Pyrrolidinone 2-indolinimine spiro compounds, and preparation method and application thereof

Abstract

The application discloses a pyrrolidone 2-indoline imine spiro compound with a structure as shown in formula A and a preparation method and application thereof. The preparation method comprises the following steps: taking benzylidene indoline-2-imine as raw material, and reacting with 2-chloro-2-aryl acetyl hydroxylamine under the action of an organic or inorganic base to obtain the target object A. The pyrrolidone 2-indoline imine spiro compound disclosed by the application has certain antibacterial activity, is a novel substance with a novel structure, raw materials are easy to obtain, reaction conditions are mild, green and environment-friendly, and operation is simple.

Description

Technical Field

[0001] This invention belongs to the fields of compound technology and medicinal chemistry, specifically a pyrrolidone 2-indolineimine spirocyclic compound, its preparation method, and its application. Background Technology

[0002] Indole rings are widely found in natural products and synthetic drugs, and related studies have shown that compounds containing indole skeletons possess a variety of important biological activities and pharmacological effects. Pyrrolidones are also present in many drug molecules. However, there is limited exploration of substances that simultaneously possess both indole and pyrrolidone spirocyclic structures. Research indicates that combining these two skeleton structures within the same molecule yields novel substances with certain antibacterial activity, which can serve as drugs or drug lead compounds. Summary of the Invention

[0003] The purpose of this invention is to provide a novel pyrrolidone 2-indolineimine spirocyclic compound, its preparation method, and its application, the structure of which is shown in Formula A:

[0004]

[0005] In the above chemical structural formula: R 1 Selected from any one of the atoms or groups of H, methoxy, and Cl; R 2 Selected from any one of the following groups: phenyl and substituted phenyl, naphthyl, pyridyl, straight-chain alkyl, branched-chain alkyl, and cycloalkyl; R 3 Selected from any one atom or group of H, allyl; R 4 Selected from any one of the groups selected from phenyl and substituted phenyl, naphthyl, and pyridyl; R 5 It is selected from any one of the groups, phenyl and ethyl.

[0006] This invention provides a method for preparing the above-described compound of formula A:

[0007]

[0008] Take benzylidene indoline-2-imine (B) and 2-chloro-2-arylacetylhydroxylamine (C), add an organic solvent and a base, react at a certain temperature, and then obtain A after post-treatment;

[0009] Furthermore, the molar ratio of compound (B) to compound (C) is 5:1-1:5, a more preferred ratio is 3:1-1:3, and a more preferred ratio is 1:2;

[0010] Furthermore, the reaction temperature is -20℃ to 50℃, with 20℃ to 25℃ being more preferred;

[0011] Furthermore, the base used is one or more of the following: triethylamine (TEA), diisopropylethylamine (DIPEA), DBU (1,8-diazabicyclo[5,4,0]undec-7-ene), DABCO (1,4-diazabicyclo[2,2,2]octane), sodium carbonate, potassium carbonate, cesium carbonate, sodium phosphate, and potassium phosphate; preferably cesium carbonate and / or potassium carbonate.

[0012] Furthermore, the reaction time is 0.5-6 hours, with 0.5-2 hours being preferred;

[0013] Furthermore, the amount of alkali used is 1-3 eq, with a preferred amount being 2.2 eq;

[0014] Furthermore, the organic solvent used is one or more of acetonitrile, dichloromethane, chloroform, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl tert-butyl ether, with tetrahydrofuran being preferred.

[0015] Furthermore, based on the above preparation method, the present invention provides compounds with the following structures:

[0016]

[0017]

[0018]

[0019] This invention also provides the application of compound A as an antibacterial active substance.

[0020] Compared with the prior art, the present invention has the following beneficial effects:

[0021] This invention yields a novel compound with a pyrrolidone-2-indolineimine spirocyclic skeleton structure. Experimental results show that most of these new compounds possess certain antibacterial activity. Detailed Implementation

[0022] The technical solution of the present invention will be further described in detail below through specific embodiments, but the present invention is not limited to these embodiments. All reagents used in the present invention are commercially available; unless otherwise specified, they are all produced using existing technology or under natural conditions of room temperature and pressure.

[0023] Example 1. Preparation of compound A

[0024] Compound B (benzylidene indoline-2-imine) 0.1 mmol, compound C (2-chloro-2-arylacetylhydroxylamine) 0.2 mmol, and cesium carbonate 0.22 mmol were added to a reaction tube, followed by 1 mL of tetrahydrofuran. The mixture was stirred at 25 °C for 0.5 h, and the reaction was monitored by TLC until completion. After concentration under reduced pressure, the product was purified by silica gel column chromatography with petroleum ether:ethyl acetate = 10:1-3:1 as the eluent. The product was collected, concentrated, and dried to obtain the target compound A.

[0025] The following compounds were prepared according to the method in Example 1:

[0026] Compound 1: N-((Z)-1'-(benzyloxy)-5'-oxo-2',4'-diphenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0027]

[0028] White solid, yield: 95%. 1 H NMR (600MHz, CDCl3) δ (ppm): 9.60 (s, 1H), 7.80 (d, J = 8.4Hz, 2H), 7.41-7.40 (m, 2H), 7.36 (d, J=6.6Hz,1H),7.34-7.31(m,7H),7.15(t,J=7.8Hz,1H),7.06(t,J=7.8Hz,1H),7.02(d,J=6. 6Hz,1H),6.84-6.79(m,3H),6.75(t,J=7.8Hz,1H),6.58(d,J=7.2Hz,2H),5.84(d,J=7.8Hz, 1H),5.31(d,J=10.2Hz,1H),5.12(s,1H),5.05(d,J=10.2Hz,1H),4.23(s,1H),2.44(s,3H). 13 C{ 1 H}NMR(151MHz, CDCl3)δ(ppm):168.9,166.7,143.7,141.2,138.1,134.8,134.0,130.3,129.6,129.5,129.4,129.2,129.1,12 8.7,128.5,128.3,127.9,127.7,126.9,125.6,125.2,123.3,110.7,77.2,65.9,60.1,52.4,21.5.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 37 H 31 N3O4SNa+ :636.1927,found:636.1917.

[0029] Compound 2: N-((Z)-1'-(benzyloxy)-2'-(4-fluorophenyl)-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0030]

[0031] Pale yellow solid, yield: 99%. 1 H NMR (600MHz, CDCl3) δ (ppm): 9.55 (s, 1H), 7.79 (d, J = 8.4Hz, 2H), 7.40-7.39 (m, 2H), 7.33-7.31(m,5H),7.18(t,J=7.8Hz,1H),7.07(t,J=7.8Hz,1H),7.05-7.02(m,2H),7 .00-6.97(m,2H),6.83-6.79(m,4H),6.57(d,J=7.8Hz,2H),5.93(d,J=7.8Hz,1H),5. 30(d,J=10.2Hz,1H),5.10(s,1H),5.03(d,J=10.8Hz,1H),4.19(s,1H),2.45(s,3H). 13 C{ 1 H}NMR(151MHz,CDCl3)δ(ppm):168.7,166.7,163.0(d, 1 J C-F =248.7Hz,1C),143.8,141.2,138.0,134.8,130.2,129.9(d, 4 J C-F =3.0Hz, 1C), 129.62, 129.6(d, 3 J C-F =7.2Hz,1C),129.5,129.4,129.2,128.6,128.4,128.0,127.8,126.9,125.4,125.2,123.5,115.8(d, 2 J C-F =21.7Hz,1C),110.8,77.3,65.3,60.0,52.3,21.6. 19 FHMR(564MHz,CDCl3)δ(ppm):-111.948.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C37 H 30 FN3O4SNa + :654.1833,found:654.1828.

[0032] Compound 3: N-((Z)-1'-(benzyloxy)-2'-(4-chlorophenyl)-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0033]

[0034] Pale yellow solid, yield: 81%. 1 H NMR (600MHz, CDCl3) δ (ppm): 9.53 (s, 1H), 7.79 (d, J = 8.4Hz, 2H), 7.40-7.38 (m, 2 H),7.34-7.31(m,7H),7.20(t,J=7.2Hz,1H),7.07(t,J=7.2Hz,1H),6.95(d,J=7. 8Hz,2H),6.85-6.79(m,4H),6.56(d,J=7.2Hz,2H),5.96(d,J=7.8Hz,1H),5.30( d,J=10.8Hz,1H),5.09(s,1H),5.03(d,J=10.2Hz,1H),4.18(s,1H),2.45(s,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 168.7, 166.7, 143.9, 141.2, 138.0, 135.0, 134.7, 132.6, 130.1, 129.7, 129.6, 129.4, 129.3, 129.1 ,129.0,128.7,128.4,128.0,127.8,126.9,125.3,125.2,123.6,110.9,77.3,65.4,59.9,52.4,21.6.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 37 H 30 35 ClN3O4SNa + :670.1538, found:670.1540; calculated for C 37 H 30 37 ClN3O4SNa + :672.1508,found:672.1516.

[0035] Compound 4: N-((Z)-1'-(benzyloxy)-2'-(4-bromophenyl)-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0036]

[0037] Pale yellow solid, yield: 97%. 1 H NMR (600MHz, CDCl3) δ (ppm): 9.69 (s, 1H), 7.80 (d, J = 8.4Hz, 2H), 7.44 (d, J = 8.4Hz, 2H) ,7.40-7.38(m,2H),7.32-7.30(m,5H),7.16(t,J=7.8Hz,1H),7.05(t,J=6.6Hz,1H),6 .88(d,J=7.8Hz,2H),6.83-6.80(m,4H),6.58(d,J=7.2Hz,2H),5.97(d,J=7.2Hz,1H), 5.29(d,J=10.8Hz,1H),5.07(s,1H),5.03(d,J=10.8Hz,1H),4.21(s,1H),2.44(s,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 168.7, 166.7, 143.9, 141.2, 138.0, 134.8, 133.2, 131.9, 130.1, 129.7, 129.6, 129.4, 129.3, 12 8.7,128.4,128.0,127.8,127.0,125.3,125.2,123.6,123.1,110.9,77.3,65.5,59.8,52.4,21.6.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 37 H 30 79 BrN3O4SNa + :714.1033, found:714.1033; calculated for C 37 H 30 81 BrN3O4SNa + :716.1012,found:716.1022.

[0038] Compound 5: N-((Z)-1'-(benzyloxy)-5'-oxo-4'-phenyl-2'-(p-methylphenyl)spiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0039]

[0040] Pale yellow solid, yield: 90%. 1 H NMR (600MHz, CDCl3) δ (ppm): 9.52 (s, 1H), 7.80 (d, J = 8.4Hz, 2H), 7.41-7.39 (m, 2H), 7.33-7.3 1(m,5H),7.18-7.17(m,1H),7.14(d,J=7.8Hz,2H)7.07(t,J=6.6Hz,1H),6.91(d,J=7.8Hz,2H) ,6.83(t,J=7.8Hz,2H),6.79-6.77(m,2H),6.58(d,J=7.2Hz,2H),5.91(d,J=7.8Hz,1H),5.29( d,J=10.8Hz,1H),5.09(s,1H),5.03(d,J=10.2Hz,1H),4.22(s,1H),2.44(s,3H),2.37(s,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 169.0, 166.7, 143.8, 141.2, 139.0, 138.2, 134.9, 131.0, 130.4, 129.6, 129.4, 129.3, 128.8, 128. 5,128.3,127.9,127.7,127.6,126.9,125.7,125.4,123.4,110.6,77.2,65.7,60.1,52.6,21.6,21.2.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 38 H 33 N3O4SNa + :650.2084,found:650.2081.

[0041] Compound 6: N-((Z)-1'-(benzyloxy)-2'-(4-methoxyphenyl)-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0042]

[0043] Pale yellow solid, yield: 61%. 1 H NMR (600MHz, CDCl3) δ (ppm): 9.47 (s, 1H), 7.79 (d, J = 8.4Hz, 2H), 7.41-7.39 (m, 2H), 7.33-7.31 (m,5H),7.18(t,J=6.6Hz,1H),7.07(t,J=7.8Hz,1H),6.94(d,J=7.8Hz,2H),6.86(d,J=8.4Hz,2 H),6.84-6.80(m,3H),6.78(d,J=7.8Hz,1H),6.57(d,J=7.2Hz,2H),5.96(d,J=7.8Hz,1H),5.2 9(d,J=10.2Hz,1H),5.08(s,1H),5.03(d,J=10.2Hz,1H),4.21(s,1H),3.82(s,3H),2.45(s,3H) 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 168.9, 166.7, 160.1, 143.7, 141.2, 138.1, 134.9, 130.4, 129.6, 129.4, 129.3, 128.9, 128.5, 128. 4,127.9,127.7,126.9,125.9,125.8,125.4,123.4,114.1,110.7,77.2,65.5,60.3,55.3,52.5,21.6.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 38 H 33 N3O5SNa + :666.2033,found:666.2029.

[0044] Compound 7: N-((Z)-1'-(benzyloxy)-2'-(3-fluorophenyl)-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0045]

[0046] Pale yellow solid, yield: 99%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.59 (s, 1H), 7.80 (d, J = 8.4Hz, 2H), 7.41-7.39 (m, 2H),7.33-7.28(m,6H),7.18(t,J=7.2Hz,1H),7.08-7.05(m,2H),6.83-6.79(m, 5H),6.74(d,J=7.8Hz,1H),6.58(d,J=7.2Hz,2H),5.95(d,J=7.2Hz,1H),5.31(d ,J=10.2Hz,1H),5.09(s,1H),5.04(d,J=11.4Hz,1H),4.22(s,1H),2.44(s,3H). 13 C{ 1 H}NMR(151MHz,CDCl3)δ(ppm):168.7,166.6,162.9(d, 1 J C-F =248.7Hz,1C),143.8,141.2,138.0,136.8(d, 4 J C-F =5.7Hz, 1C), 134.7, 130.4(d, 3 J C-F =8.8Hz,1C),130.1,129.7,129.6,129.4,129.3,128.6,128.4,127.9,127.8,126.9,125.3,125.0,123.5,123.4,116.1(d, 2 J C-F =21.6Hz, 1C), 114.9(d, 2 J C-F =20.2Hz,1C),110.9,77.3,65.5,59.9,52.3,21.5. 19 F HMR(564MHz,CDCl3)δ(ppm):-111.299.HRMS(ESI-TOF)m / z:[M+Na] + calculated for C 37 H 30 FN3O4SNa + :654.1833,found:654.1828.

[0047] Compound 8: N-((Z)-1'-(benzyloxy)-2'-(3-chlorophenyl)-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0048]

[0049] Pale yellow solid, yield: 72%. 1 H NMR (600MHz, CDCl3) δ (ppm): 9.57 (s, 1H), 7.78 (d, J=8.4Hz, 2H), 7.40-7.38 (m, 2H), 7.34 (d, J= 7.2Hz,1H),7.32-7.31(m,5H),7.25(t,J=7.8Hz,1H),7.18(t,J=7.8Hz,1H),7.06(t,J=7.2Hz,1 H),7.01(s,1H),6.88(d,J=6.6Hz,1H),6.83-6.79(m,4H),6.57(d,J=7.8Hz,2H),5.93(d,J=7.2 Hz,1H),5.29(d,J=10.2Hz,1H),5.06(s,1H),5.01(d,J=10.8Hz,1H),4.20(s,1H),2.43(s,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 168.6, 166.6, 143.8, 141.2, 138.0, 136.3, 134.9, 134.7, 130.1, 130.0, 129.8, 129.6, 129.5, 129.3, 12 8.7,128.4,127.9,127.8,127.7,126.9,126.0,125.2,125.1,123.5,111.0,77.3,65.4,59.9,52.3,21.6.HRMS(ESI-TOF)m / z:[M+Na] + calculated for C 37 H 30 35 ClN3O4SNa + :670.1538,found:670.1544; calculated for C 37 H 30 37 ClN3O4SNa + :672.1508,found:672.1509.

[0050] Compound 9: N-((Z)-1'-(benzyloxy)-2'-(3-bromophenyl)-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0051]

[0052] White solid, yield: 89%. 1 H NMR (600MHz, CDCl3) δ (ppm): 9.56 (s, 1H), 7.79 (d, J = 8.4Hz, 2H), 7.51 (d, J = 9.0Hz, 1H), 7.4 0(q,J=3.0Hz,2H),7.41-7.39(m,2H),7.33-7.32(m,5H),7.21-7.16(m,3H),7.07(t,J=7.2 Hz,1H),6.94(d,J=9.0Hz,1H),6.84-6.80(m,4H),6.58(d,J=6.6Hz,2H),5.93(d,J=7.2Hz, 1H),5.30(d,J=10.8Hz,1H),5.06(s,1H),5.02(d,J=10.8Hz,1H),4.20(s,1H),2.44(s,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 168.6, 166.6, 143.9, 141.2, 138.0, 136.5, 134.7, 132.3, 130.6, 130.2, 130.0, 129.8, 129.6, 129.5, 12 9.3,128.7,128.4,128.0,127.8,126.9,126.4,125.1,123.5,123.0,110.9,77.3,65.3,60.0,52.3,21.6.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 37 H 30 79 BrN3O4SNa + :714.1033, found:714.1033; calculated for C 37 H 30 81 BrN3O4SNa + :716.1012,found:716.1015.

[0053] Compound 10: N-((Z)-1'-(benzyloxy)-5'-oxo-4'-phenyl-2'-(m-methylphenyl)spiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide (3j).

[0054]

[0055] Pale yellow solid, yield: 92%. 1 H NMR (600MHz, CDCl3) δ (ppm): 9.51 (s, 1H), 7.80 (d, J = 8.4Hz, 2H), 7.42-7.40 (m, 2H), 7.3 3-7.31(m,5H),7.21(t,J=7.8Hz,1H),7.18-7.15(m,2H),7.07(t,J=7.8Hz,1H),6.85-6. 82(m,3H),6.79-6.75(m,3H),6.58(d,J=7.8Hz,2H),5.85(d,J=7.2Hz,1H),5.30(d,J=1 0.2Hz,1H),5.09(s,1H),5.03(d,J=10.8Hz,1H),4.23(s,1H),2.44(s,3H),2.30(s,3H). 13 C{ 1 H}NMR(151MHz, CDCl3)δ(ppm):169.0,166.7,143.8,141.1,138.6,138.1,134.9,133.9,130.4,129.9,129.6,129.5,129.3,129.1,128.8,12 8.62,128.56,128.4,127.9,127.7,126.9,125.7,125.3,125.0,123.3,110.6,77.2,65.8,60.2,52.5,21.6,21.4.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 38 H 33 N3O4SNa + :650.2084,found:650.2091.

[0056] Compound 11: N-((Z)-1'-(benzyloxy)-2'-(3-methoxyphenyl)-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide (3k).

[0057]

[0058] Pale yellow solid, yield: 60%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.49 (s, 1H), 7.79 (d, J = 8.4Hz, 2H), 7.42-7.40 (m, 2H), 7.33-7.31 (m,6H),7.18(t,J=7.8Hz,1H),7.07(t,J=7.2Hz,1H),6.90(dd,J=8.4,2.4Hz,1H),6.84-6.77( m,4H),6.66(d,J=6.0Hz,1H),6.58(d,J=7.2Hz,2H),6.50(s,1H),5.97(d,J=7.8Hz,1H),5.30( d,J=10.2Hz,1H),5.08(s,1H),5.04(d,J=10.2Hz,1H),4.23(s,1H),3.69(s,3H),2.45(s,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 168.9, 166.6, 158.8, 143.6, 141.3, 138.2, 134.9, 134.0, 131.7, 129.6, 129.4, 129.2, 129.04, 128.97, 128.7, 128.5,128.3,127.7,126.7,125.8,125.2,123.3,121.7,114.2,114.0,110.8,77.1,65.8,60.0,54.7,52.2,21.5.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 38 H 33 N3O5SNa + :666.2033,found:666.2036.

[0059] Compound 12: N-((Z)-1'-(benzyloxy)-2'-(2-fluorophenyl)-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0060]

[0061] Pale yellow solid, yield: 99%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.57 (s, 1H), 7.79 (d, J = 8.4Hz, 2H), 7.41-7.40 (m, 3H),7.38-7.31(m,7H),7.21(t,J=7.2Hz,1H),7.07(t,J=7.2Hz,1H),6.88-6.8 7(m,1H),6.85-6.79(m,4H),6.61(d,J=7.2Hz,2H),6.05-5.89(m,1H),5.41(s, 1H), 5.30 (d, J = 10.2Hz, 1H), 4.98 (d, J = 10.2Hz, 1H), 4.17 (s, 1H), 2.43 (s, 3H). 13 C{ 1 H}NMR(151MHz,CDCl3)δ(ppm):168.6,166.8,160.8(d, 1 J C-F =248.7Hz,1C),143.7,141.4,138.2,134.6,130.7(d, 3 J C-F =7.2Hz,1C),130.1,129.7,129.6,129.5,129.3,128.6,128.4,127.9,127.7,126.8,125.6,124.5(d, 4 J C-F =2.9Hz,1C),123.9,123.4,121.96,121.88,115.8(d, 2 J C-F =20.2Hz,1C),110.9,77.1,59.86,59.47,52.2,21.5. 19 FHMR(564MHz,CDCl3)δ(ppm):-116.672.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 37 H 30 FN3O4SNa + :654.1833,found:654.1836.

[0062] Compound 13: N-((Z)-1'-(benzyloxy)-2'-(2-chlorophenyl)-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0063]

[0064] Pale yellow solid, yield: 99%. 1 H NMR (600MHz, CDCl3) δ (ppm): 9.64 (s, 1H), 7.81 (d, J = 8.4Hz, 2H), 7.48 (dd, J = 8.4, 1.8Hz, 1H), 7.41-7.38(m,3H),7.32-7.30(m,6H),7.21-7.18(m,2H),7.08(t,J=7.2Hz,1H),6.87-6.85(m, 2H),6.80(d,J=7.8Hz,1H),6.78-6.76(t,J=7.2Hz,1H),6.63(d,J=6.6Hz,2H),5.90(d,J=7.2H z,1H),5.52(s,1H),5.31(d,J=10.2Hz,1H),4.95(d,J=10.2Hz,1H),4.16(s,1H),2.43(s,3H). 13 C{ 1 H}NMR(151MHz, CDCl3)δ(ppm):168.7,166.7,143.7,141.7,138.3,135.0,134.6,131.8,130.1,130.0,129.9,129.61,129.56,129.3,1 28.6,128.4,127.9,127.8,127.5,127.3,126.8,126.0,123.7,123.4,110.8,77.1,62.7,59.3,52.5,21.5.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 37 H 30 35 ClN3O4SNa + :670.1538,found:670.1535; calculated for C 37 H 30 37 ClN3O4SNa + :672.1508,found:672.1517.

[0065] Compound 14: N-((Z)-1'-(benzyloxy)-2'-(2-bromophenyl)-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0066]

[0067] Pale yellow solid, yield: 99%. 1 H NMR (600MHz, CDCl3) δ (ppm): 9.65 (s, 1H), 7.82 (d, J = 8.4Hz, 2H), 7.47 (dd, J = 8.4, 2.4Hz, 1H), 7.43 (t, J = 8.4Hz,1H),7.39-7.37(m,3H),7.32-7.29(m,5H),7.23(t,J=8.4Hz,1H),7.19(t,J=7.8Hz,1H),7.08(t,J =7.8Hz,1H),6.89-6.86(m,2H),6.79(d,J=7.8Hz,1H),6.77(t,J=7.2Hz,1H),6.64(d,J=6.6Hz,2H),5.88 (d,J=7.2Hz,1H),5.50(s,1H),5.30(d,J=10.2Hz,1H),4.93(d,J=10.2Hz,1H),4.16(s,1H),2.42(s,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 168.7, 166.7, 143.7, 141.9, 138.3, 134.6, 133.2, 133.1, 130.3, 130.0, 129.60, 129.57, 129.5, 129.3, 12 8.6,128.4,127.93,127.85,127.8,126.8,126.1,125.6,123.8,123.4,110.8,77.1,64.8,59.3,52.6,21.5.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 37 H 30 79 BrN3O4SNa + :714.1033, found:714.1027; calculated for C 37 H 30 81 BrN3O4SNa + :716.1012,found:716.1007.

[0068] Compound 15: N-((Z)-1'-(benzyloxy)-5'-oxo-4'-phenyl-2'-(o-methylphenyl)spiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0069]

[0070] Pale yellow solid, yield: 98%. 1 H NMR (600MHz, CDCl3) δ (ppm): 9.65 (s, 1H), 7.82 (d, J = 8.4Hz, 2H), 7.42-7.40 (m, 2H), 7.38 (d, J = 6.6H) z,2H),7.34-7.30(m,5H),7.28-7.25(m,2H),7.16(t,J=8.4Hz,1H),7.05(t,J=7.2Hz,1H),6.97(d,J =7.2Hz,1H),6.81-6.78(m,3H),6.73(t,J=7.8Hz,1H),6.58(d,J=7.2Hz,2H),5.80(d,J=7.2Hz,1H), 5.33(d,J=11.4Hz,1H),5.22(s,1H),5.05(d,J=10.8Hz,1H),4.19(s,1H),2.46(s,3H),1.34(s,3H). 13 C{ 1 H}NMR(151MHz, CDCl3)δ(ppm):168.8,166.9,143.7,141.2,138.2,137.2,135.2,131.8,130.9,130.2,129.6,129.5,129.4,129.1,128.7,1 28.5,128.3,127.9,127.6,126.8,126.4,125.8,125.7,124.4,123.4,110.6,77.4,62.7,59.5,52.4,21.5,18.3.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 38 H 33 N3O4SNa + :650.2084,found:650.2084.

[0071] Compound 16: N-((Z)-1'-(benzyloxy)-2'-(2,4-dichlorophenyl)-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0072]

[0073] Pale yellow solid, yield: 94%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.70 (s, 1H), 7.80 (d, J = 7.2Hz, 2H), 7.41 (d, J = 8.4Hz, 1H), 7.37-7.26 (m, 9H), 7.20 (s, 1H), 7.06 (t, J = 7.2Hz, 1H), 6.85 -6.82(m,4H),6.62(d,J=7.8Hz,2H),6.01(d,J=7.8Hz,1H),5.44(s,1H), 5.29(d,J=10.8Hz,1H),4.94(d,J=10.8Hz,1H),4.15(s,1H),2.42(s,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 168.5, 166.7, 143.7, 141.7, 138.2, 135.5, 135.3, 134.5, 130.5, 129.8, 129.70, 129.67, 129.6, 129.5, 129. 2,128.7,128.5,128.4,127.9,127.8,127.6,126.7,125.7,123.6,123.5,111.0,77.2,62.4,59.1,52.3,21.5.HRMS(ESI-TOF)m / z:[M+Na] + calculated for C 37 H 30 35 Cl2N3O4SNa + :704.1148, found:704.1141; calculated for C 37 H 30 35 Cl 37 ClN3O4SNa + :706.1119,found:706.1123; calculated for,C 37 H 30 37 Cl2N3O4SNa + :708.1089,found:708.1094.

[0074] Compound 17: N-((Z)-1'-(benzyloxy)-2'-(3,4-dimethylphenyl)-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0075]

[0076] Pale yellow solid, yield: 99%. 1 H NMR (600MHz, CDCl3) δ (ppm): 9.58 (s, 1H), 7.80 (d, J = 8.4Hz, 2H), 7.42-7.41 (m, 2H), 7 .33-7.29(m,5H),7.15(t,J=7.8Hz,1H),7.08-7.05(m,5H),6.84-6.76(m,5H),6.73-6 .72(m,1H),6.59(d,J=7.8Hz,2H),5.90(d,J=7.8Hz,1H),5.29(d,J=10.2Hz,1H),5.0 6(s,1H),5.03(d,J=10.8Hz,1H),4.25(s,1H),2.44(s,3H),2.27(s,3H),2.20(s,3H). 13 C{ 1 H}NMR(151MHz, CDCl3)δ(ppm):169.0,166.7,143.7,141.1,138.2,137.5,137.1,134.9,131.2,130.4,129.9,129.6,129.5,129.4,129.3,128.5 ,128.3,127.9,127.6,126.9,125.7,125.4,125.28,125.26,123.2,110 .6,77.1,65.7,60.2,52.5,21.5,19.7,19.5.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 39 H 35 N3O4SNa + :664.2240,found:664.2242.

[0077] Compound 18: N-((Z)-1'-(benzyloxy)-2'-(1-naphthyl)-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0078]

[0079] Pale yellow solid, yield: 72%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.64 (s, 1H), 7.88 (d, J = 8.4Hz, 1H), 7.85 (d, J = 8.4Hz, 2H), 7.77 (d, J = 8.4Hz, 1H), 7.65 (d, J=7.2Hz,1H),7.57(t,J=7.8Hz,1H),7.41-7.40(m,2H),7.35(d,J=8.4Hz,2H),7.29(d,J=6.6Hz,1H),7.28-7.26(m,4H ),7.08-7.04(m,2H),6.92-6.89(m,2H),6.83-6.81(m,2H),6.69(d,J=7.8Hz,1H),6.60(d,J=6.6Hz,2H),6.29(t,J=7. 8Hz,1H),5.94(s,1H),5.55(d,J=7.8Hz,1H),5.38(d,J=10.2Hz,1H),5.09(d,J=10.2Hz,1H),4.25(s,1H),2.46(s,3H). 13 C{ 1 H}NMR(151MHz,CDCl3)δ(ppm):168.9,166.9,143.8,140.8,138.2,134.8, 133.5,131.6,130.4,129.7,129.6,129.5,129.3,129.2,128.62,128.57,1 28.4,127.9,127.7,126.9,126.1,126.0,125.6,125.1,124.2,124.0,123 .0,121.7,110.4,77.2,62.4,59.8,52.5,21.6.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 41 H 33 N3O4SNa + :686.2084,found:686.2085.

[0080] Compound 19: N-((Z)-1'-(benzyloxy)-2'-(2-naphthyl)-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0081]

[0082] Pale yellow solid, yield: 98%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.70 (s, 1H), 7.85-7.84 (m, 3H), 7.79 (d, J = 7.8Hz, 1H), 7.76 (d, J = 9.0Hz, 1H),7.66(s,1H),7.54-7.49(m,2H),7.41-7.39(m,2H),7.33(d,J=7.8Hz,2H),7.31-7.27(m,4H),7.1 0(t,J=8.4Hz,1H),7.07(t,J=7.8Hz,1H),6.96(s,1H),6.85-6.81(m,3H),6.63-6.58(m,3H),5.81(d, J=7.8Hz,1H),5.35(d,J=10.2Hz,1H),5.30(s,1H),5.09(d,J=10.8Hz,1H),4.35(s,1H),2.45(s,3H). 13 C{ 1 H}NMR(151MHz,CDCl3)δ(ppm):168.9,166.8,143.7,141.2,138.1,134.8, 133.4,132.9,131.4,130.3,129.6,129.48,129.45,129.2,128.5,128.4, 128.3,128.2,127.9,127.69,127.67,126.9,126.65,126.61,125.4,125. 2,123.3,110.8,77.2,66.0,60.1,52.5,21.5.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 41 H 33 N3O4SNa + :686.2084,found:686.2090.

[0083] Compound 20: N-((Z)-1'-(benzyloxy)-5'-oxo-4'-phenyl-2'-(2-pyridyl)spiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0084]

[0085] Yellow solid, yield: 35% 1H NMR (600MHz, CDCl3) δ (ppm): 9.53 (s, 1H), 8.62 (d, J = 4.8Hz, 1H), 7.78 (d, J = 7.8Hz, 2H), 7.63 (t, J = 7.2H z,1H),7.39-7.37(m,2H),7.31-7.26(m,6H),7.14(t,J=7.8Hz,1H),7.05(t,J=7.8Hz,1H),7.00(d,J=7. 8Hz,1H),6.83-6.80(m,2H),6.77(d,J=7.8Hz,1H),6.73(t,J=7.8Hz,1H),6.59(d,J=6.6Hz,2H),5.90( d,J=7.8Hz,1H),5.24(d,J=10.8Hz,1H),5.04(s,1H),4.98(d,J=10.8Hz,1H),4.57(s,1H),2.43(s,3H). 13 C{ 1 H}NMR(151MHz, CDCl3)δ(ppm):168.6,167.9,154.4,149.8,143.7,141.3,138.1,136.9,135.1,130.7,129.6,129.52,129.45,129.4,1 28.6,128.4,127.9,127.6,126.9,125.9,124.4,124.0,123.5,123.4,110.9,77.5,67.0,59.6,52.9,21.6.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 36 H 30 N4O4SNa + :637.1880,found:637.1878.

[0086] Compound 21: N-((Z)-1'-(benzyloxy)-2'-cyclopentyl-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0087]

[0088] Pale yellow solid, yield: 78%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.51 (s, 1H), 7.79 (d, J = 8.4Hz, 2H), 7.52-7.51 (m, 2H), 7.42-7.38 (m, 4H), 7. 33-7.30(m,3H),7.22(t,J=7.8Hz,1H),7.11(t,J=7.2Hz,1H),6.94-6.92(m,2H),6.83(d,J=7.8Hz,1H),6 .65(d,J=7.8Hz,2H),5.41(d,J=9.0Hz,1H),4.86(d,J=9.6Hz,1H),4.04(s,1H),4.00(d,J=9.6Hz,1H),2. 45(s,3H),2.36-2.28(m,2H),2.14-2.08(m,1H),1.47-1.41(m,1H),1.36-1.28(m,3H),1.16-1.03(m,2H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 167.9, 166.2, 143.6, 141.0, 138.5, 134.7, 130.2, 129.6, 129.55, 129.52, 129.47, 128.8, 128.5, 12 7.92,127.89,126.8,124.2,122.7,111.1,78.0,69.0,59.9,56.4,40.1,32.9,28.1,24.6,24.2,21.6.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 36 H 35 N3O4SNa + :628.2240,found:628.2232.

[0089] Compound 22: N-((Z)-1'-(benzyloxy)-2'-butyl-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0090]

[0091] Pale yellow solid, yield: 63%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.57 (s, 1H), 7.77 (d, J = 7.2Hz, 2H), 7.51-7.48 (m, 2H), 7.40-7.39 (m, 4H), 7.34-7. 30(m,3H),7.23(t,J=6.6Hz,1H),7.09(t,J=7.2Hz,1H),6.90(t,J=7.2Hz,2H),6.86(d,J=7.8Hz,1H),6.69(d,J =7.8Hz,2H),5.37(d,J=9.6Hz,1H),4.83(d,J=9.6Hz,1H),4.09(s,1H),4.04-4.02(m,1H),2.44(s,3H),1.87-1 .83(m,1H),1.56-1.53(m,1H),1.04-0.97(m,2H),0.95-0.84(m,1H),0.76-0.73(m,1H),0.62(t,J=7.2Hz,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 168.2, 165.6, 143.6, 141.2, 138.4, 134.9, 130.6, 129.7, 129.52, 129.48, 129.4, 128.9, 128.6, 12 8.3,127.9,127.8,126.8,124.2,122.7,111.0,78.8,64.3,59.4,55.3,27.7,27.2,22.4,21.6,13.5.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 35 H 36 N3O4SH + :594.2421,found:594.2429.

[0092] Compound 23: N-((Z)-1'-(benzyloxy)-2'-isobutyl-5'-oxo-4'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0093]

[0094] White solid, yield: 99%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.56 (s, 1H), 7.77 (d, J = 8.4Hz, 2H), 7.48 (d, J = 7.8Hz, 2H), 7.43-7.40 (m, 3H), 7 .35-7.30(m,4H),7.22(t,J=7.8Hz,1H),7.10(t,J=7.8Hz,1H),6.93-6.90(m,2H),6.87(d,J=7.2Hz,1H),6.7 1(d,J=7.2Hz,2H),5.38(d,J=10.2Hz,1H),4.81(d,J=9.6Hz,1H),4.13(t,J=6.6Hz,1H),4.10(s,1H),2.44(s ,3H),1.71-1.66(m,1H),1.39-1.34(m,1H),1.22-1.16(m,1H),0.61(d,J=6.6Hz,3H),0.54(d,J=6.0Hz,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 168.2, 165.6, 143.6, 141.2, 138.4, 134.9, 130.6, 129.8, 129.7, 129.5, 129.4, 128.9, 128.6, 128 .0,127.9,127.8,126.9,124.1,122.7,111.0,78.7,61.9,59.5,55.3,36.5,24.2,22.8,22.1,21.6.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 35 H 35 N3O4SNa + :616.2240,found:616.2248.

[0095] Compound 24: (Z)-1'-(benzyloxy)-5'-oxo-4'-phenyl-2-(p-methylsulfonylimide)spiro[indoline-3,3'-pyrrolline]-2'-carboxylic acid ethyl ester

[0096]

[0097] Pale yellow solid, yield: 64%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.81 (s, 1H), 7.89 (d, J = 8.4Hz, 2H), 7.51 (d, J = 6.0Hz, 2H), 7.40-7.35 (m, 5H),7.04(t,J=8.4Hz,1H),6.96(t,J=7.8Hz,1H),6.89-6.86(m,2H),6.75(t,J=7.2Hz,1H),6.70(d,J= 7.2Hz,1H),6.68(d,J=7.8Hz,1H),6.49(d,J=6.6Hz,2H),5.30(d,J=11.4Hz,1H),5.17(d,J=11.4Hz,1H ),4.50(s,1H),4.27-4.22(m,1H),4.17-4.13(m,1H),4.12(s,1H),2.46(s,3H),1.28(t,J=6.6Hz,3H). 13 C{ 1 H}NMR(151MHz, CDCl3)δ(ppm):171.0,165.8,165.6,144.0,139.7,137.8,135.5,131.1,129.6,129.5,129.04,128.99,128.92 ,128.7,128.2,128.0,127.6,126.9,124.1,123.6,110.9,77.5,67.1,62.5,57.6,53.7,21.6,14.0.HRMS(ESI-TOF)m / z:[M+H] + Calculated for C 34 H 31 N3O6SH + :610.2006,found:610.2013.

[0098] Compound 25: N-((Z)-1'-(benzyloxy)-5-methoxy-5'-oxo-2',4'-diphenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0099]

[0100] Pale yellow solid, yield: 68%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.49 (s, 1H), 7.79 (d, J = 8.4Hz, 2H), 7.42-7.40 (m, 2H),7.38-7.35(m,3H),7.32-7.31(m,5H),7.08-7.05(m,3H),6.84-6.82(m,2H ),6.71-6.67(m,2H),6.60(d,J=7.2Hz,2H),5.40(s,1H),5.31(d,J=10.8,Hz,1 H),5.13(s,1H),5.05(d,J=10.2Hz,1H),4.20(s,1H),3.39(s,3H),2.44(s,3H). 13 C{ 1 H}NMR(151MHz, CDCl3)δ(ppm):168.9,166.7,156.0,143.6,138.3,134.9,134.6,134.2,130.3,129.6,129.4,129.3,129.0,128.8,1 28.5,128.3,127.9,127.8,127.7,126.9,126.8,115.8,111.4,110.4,77.2,65.8,60.2,55.5,52.5,21.5.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 38 H 33 N3O5SNa + :666.2033,found:666.2036.

[0101] Compound 26: N-((Z)-1'-(benzyloxy)-6-chloro-5'-oxo-2',4'-diphenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0102]

[0103] Yellow solid, yield: 37%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.52 (s, 1H), 7.79 (d, J = 8.4Hz, 2H), 7.40-7.36 (m, 3H), 7. 35-7.28(m,7H),7.09(t,J=7.8Hz,1H),7.02(d,J=7.2Hz,2H),6.87-6.84(m,2H),6.79( s,1H),6.73(dd,J=8.4Hz,J=1.8Hz,1H),6.58(d,J=7.2Hz,2H),5.72(d,J=8.4Hz,1H), 5.29(d,J=11.4Hz,1H),5.09(s,1H),5.02(d,J=10.2Hz,1H),4.18(s,1H),2.46(s,3H). 13 C{ 1 H}NMR(151MHz, CDCl3)δ(ppm):168.8,166.5,144.1,142.2,137.8,135.4,134.8,133.8,130.1,129.7,129.5,129.3,128.9,12 8.7,128.4,128.1,127.9,127.7,127.0,126.1,124.1,123.5,111.3,77.3,65.9,59.8,52.5,21.6.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 37 H 30 35 ClN3O4SNa + :670.1538, found:670.1528; calculated for C 37 H 30 37 ClN3O4SNa + :672.1508,found:672.1509.

[0104] Compound 27: N-((Z)-1-allyl-1'-(benzyloxy)-5'-oxo-2',4'-diphenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0105]

[0106] White solid, yield: 85%. 1H NMR (600MHz, CDCl3) δ (ppm): 7.99 (d, J = 8.4Hz, 2H), 7.38-7.32 (m, 3H), 7.27-7.23 (m, 4H), 7.22-7 .17(m,5H),7.15-7.13(m,2H),7.09(d,J=6.6Hz,2H),6.82-6.78(m,3H),6.76(d,J=8.4Hz,1H),5. 79(d,J=7.2Hz,1H),5.18(s,1H),5.17-5.12(m,1H),5.09-5.05(m,1H),4.99(d,J=10.2Hz,1H),4 .77(d,J=17.4Hz,1H),4.37(dd,J=16.8,6.6Hz,1H),4.23-4.19(m,2H),4.19(s,1H),2.06(s,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 166.2, 164.5, 144.1, 143.2, 140.2, 134.6, 134.2, 130.7, 130.0, 129.6, 129.5, 129.3, 129.2, 129.0, 128.8 ,128.5,128.18,128.16,127.7,127.2,126.4,124.8,123.8,118.1,110.8,76.3,65.4,60.0,54.3,48.3,21.1.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 40 H 35 N3O4SNa + :676.2240,found:676.2242.

[0107] Compound 28: N-((Z)-1'-(benzyloxy)-4'-(4-fluorophenyl)-5'-oxo-2'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0108]

[0109] Pale yellow solid, yield: 83%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.67 (s, 1H), 7.79 (d, J = 8.4Hz, 2H), 7.41-7.39 (m, 2H), 7.37 (t ,J=7.8Hz,1H),7.34-7.31(m,7H),7.17(t,J=7.2Hz,1H),7.00(d,J=7.8Hz,2H),6.83(d,J= 7.8Hz,1H),6.75(t,J=7.8Hz,1H),6.57-6.55(m,2H),6.49-6.46(m,2H),5.84(d,J=7.8Hz, 1H),5.29(d,J=10.2Hz,1H),5.10(s,1H),5.03(d,J=10.2Hz,1H),4.21(s,1H),2.45(s,3H). 13 C{ 1 H}NMR(151MHz,CDCl3)δ(ppm):168.8,166.7,162.2(d, 1 J C-F =255.9Hz,1C),144.0,141.2,138.1,134.8,133.9,131.1(d, 3 J C-F =7.2Hz,1C),129.7,129.3,129.1,128.8,128.6,128.4,127.7,126.9,126.2(d, 4 J C-F =3.0Hz,1C),125.5,125.1,123.5,114.8(d, 2 J C-F =21.7Hz,1C),110.9,77.2,65.9,60.0,51.6,21.5. 19 F HMR(564MHz,CDCl3)δ(ppm):-113.786.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 37 H 30 FN3O4SNa + :654.1833,found:654.1840.

[0110] Compound 29: N-((Z)-1'-(benzyloxy)-4'-(4-chlorophenyl)-5'-oxo-2'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0111]

[0112] Pale yellow solid, yield: 87%. 1 H NMR (600MHz, CDCl3) δ (ppm): 9.73 (s, 1H), 7.77 (d, J = 8.4Hz, 2H), 7.42-7.41 (m, 2H), 7.36 (t ,J=7.8Hz,1H),7.33-7.30(m,7H),7.16(t,J=7.8Hz,1H),6.98(d,J=6.6Hz,2H),6.85(d,J= 7.2Hz,1H),6.74(t,J=7.8Hz,1H),6.71-6.69(m,2H),6.52-6.50(m,2H),5.83(d,J=7.8Hz, 1H),5.30(d,J=10.8Hz,1H),5.09(s,1H),5.05(d,J=10.8Hz,1H),4.20(s,1H),2.46(s,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 168.8, 166.5, 144.0, 141.2, 138.0, 134.8, 133.9, 133.6, 130.6, 129.7, 129.3, 129.1, 129.0, 12 8.8,128.6,128.4,128.0,127.7,126.9,125.4,125.1,123.5,111.0,77.3,66.0,59.9,51.4,21.6.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 37 H 30 35 ClN3O4SNa + :670.1538,found:670.1544; calculated for C 37 H 30 37 ClN3O4SNa + :672.1508,found:672.1510.

[0113] Compound 30: N-((Z)-1'-(benzyloxy)-4'-(4-bromophenyl)-5'-oxo-2'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0114]

[0115] Pale yellow solid, yield: 91%.1 H NMR (600MHz, CDCl3) δ (ppm): 9.71 (s, 1H), 7.76 (d, J = 8.4Hz, 2H), 7.43-7.41 (m, 2H), 7. 37(t,J=7.2Hz,1H),7.38-7.30(m,8H),7.17(t,J=7.2Hz,1H),6.98(d,J=7.8Hz,2H),6 .85-6.83(m,3H),6.74(t,J=7.2Hz,1H),6.44(d,J=9.0Hz,2H),5.83(d,J=7.8Hz,1H), 5.30(d,J=10.8Hz,1H),5.08(s,1H),5.05(d,J=10.2Hz,1H),4.18(s,1H),2.48(s,3H). 13 C{ 1 H}NMR(151MHz, CDCl3)δ(ppm):168.8,166.4,144.0,141.1,138.0,134.8,133.9,131.0,130.9,129.7,129.5,129.3,129.2,12 8.8,128.6,128.4,127.7,126.9,125.4,125.1,123.5,121.9,110.9,77.3,66.0,59.8,51.4,21.6.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 37 H 30 79 BrN3O4SNa + :714.1033, found:714.1038; calculated for C 37 H 30 81 BrN3O4SNa + :716.1012,found:716.1014.

[0116] Compound 31: N-((Z)-1'-(benzyloxy)-5'-oxo-2'-phenyl-4'-(p-methylphenyl)spiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0117]

[0118] Yellow solid, yield: 88%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.57 (s, 1H), 7.81 (d, J = 7.8Hz, 2H), 7.40-7.35 (m, 3H), 7.33- 7.31(m,7H),7.15(t,J=7.8Hz,1H),7.02-7.01(m,2H),6.79(d,J=7.8Hz,1H),6.74(t,J=7 .2Hz,1H),6.61(d,J=7.8Hz,2H),6.47(d,J=7.2Hz,2H),5.83(d,J=7.8Hz,1H),5.30(d,J= 10.2Hz,1H),5.10(s,1H),5.03(d,J=10.8Hz,1H),4.19(s,1H),2.45(s,3H),2.17(s,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 169.1, 166.9, 143.7, 141.1, 138.2, 137.2, 134.9, 134.1, 129.5, 129.4, 129.2, 129.0, 128.7, 128. 6,128.5,128.3,127.7,127.2,126.9,125.8,125.2,123.3,110.7,77.2,65.9,60.2,52.2,21.6,21.1.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 38 H 33 N3O4SNa + :650.2084,found:650.2081.

[0119] Compound 32: N-((Z)-1'-(benzyloxy)-4'-(3-chlorophenyl)-5'-oxo-2'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0120]

[0121] Pale yellow solid, yield: 87%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.58 (s, 1H), 7.81 (d, J = 8.4Hz, 2H), 7.38-7.33 (m, 5H), 7.31 -7.29(m,5H),7.18(t,J=7.2Hz,1H),7.07-7.06(m,1H),7.01(d,J=7.2Hz,2H),6.84(d,J =7.8Hz,1H),6.78-6.75(m,2H),6.63(s,1H),6.59(d,J=7.2Hz,1H),5.84(d,J=7.8Hz,1H ),5.21(d,J=10.2Hz,1H),5.09(s,1H),4.94(d,J=10.2Hz,1H),4.21(s,1H),2.41(s,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 168.5, 166.2, 143.8, 141.2, 138.0, 134.7, 133.8, 133.6, 132.5, 129.8, 129.7, 129.4, 129.21, 129.17, 12 8.8,128.6,128.4,128.1,127.69,127.66,126.8,125.3,125.1,123.6,110.9,77.2,65.9,59.8,51.8,21.5.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 37 H 30 35 ClN3O4SNa + :670.1538, found:670.1530; calculated for C 37 H 30 37 ClN3O4SNa + :672.1508,found:672.1514.

[0122] Compound 33: N-((Z)-1'-(benzyloxy)-4'-(3-bromophenyl)-5'-oxo-2'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0123]

[0124] Pale yellow solid, yield: 89%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.58 (s, 1H), 7.82 (d, J = 7.8Hz, 2H), 7.38-7.31 (m, 1 0H),7.22(d,J=7.2Hz,1H),7.19(t,J=7.8Hz,1H),7.01(d,J=6.0Hz,2H),6.84(d, J=7.2Hz,1H),6.78-6.75(m,2H),6.72-6.67(m,2H),5.84(d,J=7.2Hz,1H),5.20( d,J=10.2Hz,1H),5.08(s,1H),4.93(d,J=10.2Hz,1H),4.20(s,1H),2.40(s,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 168.5, 166.1, 143.8, 141.2, 138.0, 134.7, 133.8, 132.7, 132.2, 131.0, 129.8, 129.7, 129.5, 129.2, 12 8.8,128.6,128.4,128.2,127.7,126.8,125.3,125.1,123.6,121.8,110.9,77.2,65.9,59.9,51.7,21.5.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 37 H 30 79 BrN3O4SNa + :714.1033, found:714.1024; calculated for C 37 H 30 81 BrN3O4SNa + :716.1012,found:716.1013.

[0125] Compound 34: N-((Z)-1'-(benzyloxy)-5'-oxo-2'-phenyl-4'-(m-methylphenyl)spiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0126]

[0127] Pale yellow solid, yield: 88%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.51 (s, 1H), 7.83 (d, J = 8.4Hz, 2H), 7.37-7.32 (m, 5H), 7.31-7. 29(m,5H),7.15(t,J=7.8Hz,1H),7.03(d,J=7.8Hz,2H),6.91(d,J=6.6Hz,1H),6.78(d,J=7.2 Hz,1H),6.77-6.72(m,2H),6.55(s,1H),6.40(d,J=7.8Hz,1H),5.84(d,J=7.8Hz,1H),5.24(d ,J=10.2Hz,1H),5.09(s,1H),4.92(d,J=10.8Hz,1H),4.21(s,1H),2.40(s,3H),2.04(s,3H). 13 C{ 1 H}NMR(151MHz, CDCl3)δ(ppm):168.9,166.9,143.7,141.2,138.3,137.5,134.8,134.1,130.2,130.1,129.6,129.4,129.2,129.1,128.7,1 28.6,128.5,128.3,127.8,127.7,126.8,126.5,125.7,125.2,123.3,110.6,77.1,65.8,60.1,52.6,21.5,21.1.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 38 H 33 N3O4SNa + :650.2084,found:650.2079.

[0128] Compound 35: N-((Z)-1'-(benzyloxy)-4'-(3-methoxyphenyl)-5'-oxo-2'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0129]

[0130] Pale yellow solid, yield: 82%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.62 (s, 1H), 7.79 (d, J = 8.4Hz, 2H), 7.38-7.36 (m, 3H), 7.33 (d, J = 7. 8Hz,2H),7.31-7.28(m,5H),7.15(t,J=7.8Hz,1H),7.02(d,J=7.2Hz,2H),6.82(d,J=7.8Hz,1H),6 .76-6.72(m,2H),6.64-6.62(m,1H),6.31(d,J=7.2Hz,1H),6.09(s,1H),5.85(d,J=7.2Hz,1H),5. 25(d,J=10.8Hz,1H),5.08(s,1H),4.95(d,J=10.2Hz,1H),4.22(s,1H),3.44(s,3H),2.41(s,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 168.9, 166.6, 158.8, 143.6, 141.3, 138.2, 134.9, 134.0, 131.7, 129.6, 129.4, 129.2, 129.04, 128.97, 128.7, 128.5,128.3,127.7,126.7,125.8,125.2,123.3,121.7,114.2,114.0,110.8,77.1,65.8,60.0,54.7,52.2,21.5.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 38 H 33 N3O5SNa + :666.2033,found:666.2031.

[0131] Compound 36: N-((Z)-1'-(benzyloxy)-4'-(2-chlorophenyl)-5'-oxo-2'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0132]

[0133] Pale yellow solid, yield: 90%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.70 (s, 1H), 7.82 (d, J = 8.4Hz, 2H), 7.35-7.26 (m, 11 H),7.11(t,J=7.8Hz,1H),7.03(d,J=7.2Hz,2H),7.00-6.98(m,2H),6.81(t,J=7.2 Hz,1H),6.77(d,J=7.8Hz,1H),6.73(t,J=7.8Hz,1H),6.12(d,J=7.2Hz,1H),5.23 (d,J=10.2Hz,1H),5.14(s,1H),5.00(d,J=10.2Hz,1H),4.87(s,1H),2.42(s,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 168.2, 167.7, 143.8, 140.6, 138.1, 135.0, 134.6, 133.5, 132.8, 129.6, 129.4, 129.3, 129.2, 129.1, 129.04 ,128.95,128.6,128.5,128.4,128.3,127.8,126.9,126.5,125.2,123.0,110.5,77.1,66.8,59.9,49.3,21.5.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 37 H 30 35 ClN3O4SNa + :670.1538,found:670.1540; calculated for C 37 H 30 37 ClN3O4SNa + :672.1508,found:672.1509.

[0134] Compound 37: N-((Z)-1'-(benzyloxy)-5'-oxo-2'-phenyl-4'-(o-methylphenyl)spiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0135]

[0136] White solid, yield: 92%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.66 (s, 1H), 7.83 (d, J=8.4Hz, 2H), 7.40-7.37 (m, 2H), 7.36 (d, J= 7.2Hz,1H),7.33-7.30(m,7H),7.12-7.10(m,2H),7.06(d,J=7.8Hz,2H),6.97(t,J=7.2Hz,1H) ,6.80-6.77(m,2H),6.70(t,J=7.8Hz,1H),6.64(t,J=7.8Hz,1H),5.90(d,J=7.8Hz,1H),5.29( d,J=10.2Hz,1H),5.20(s,1H),5.08(d,J=10.2Hz,1H),4.51(s,1H),2.45(s,3H),1.41(s,3H). 13 C{ 1 H}NMR(151MHz, CDCl3)δ(ppm):168.9,168.4,143.7,140.9,138.0,137.4,134.8,134.0,131.5,129.9,129.6,129.4,129.3,129.2,129.0,12 8.6,128.5,128.3,127.8,127.7,126.9,126.02,125.96,125.6,123.0,110.8,77.2,66.4,59.9,49.9,21.5,19.3.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 38 H 33 N3O4SNa + :650.2084,found:650.2092.

[0137] Compound 38: N-((Z)-1'-(benzyloxy)-5'-oxo-2'-phenyl-4'-(3-pyridyl)spiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0138]

[0139] Yellow solid, yield: 86%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.59 (s, 1H), 8.32-8.31 (m, 1H), 7.80 (d, J = 8.4Hz, 2H), 7.53 (s,1H),7.39-7.34(m,6H),7.32-7.30(m,11H),7.17(t,J=7.2Hz,1H),7.01(d,J=6.6Hz,2 H),6.82(d,J=7.8Hz,1H),6.80-6.78(m,1H),6.76(t,J=7.8Hz,1H),5.86(d,J=8.4Hz,1H ),5.23(d,J=10.2Hz,1H),5.09(s,1H),4.93(d,J=10.8Hz,1H),4.25(s,1H),2.42(s,3H). 13 C{ 1 H}NMR (151MHz, CDCl3) δ (ppm): 168.4, 166.0, 150.0, 149.1, 144.0, 141.0, 138.0, 137.7, 134.6, 133.7, 130.0, 129.7, 129.3, 129.2, 128 .8,128.7,128.4,127.6,126.85,126.78,125.2,124.8,123.8,123.1,111.0,77.2,65.9,59.8,49.8,21.5.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 36 H 30 N4O4SNa + :637.1880,found:637.1877.

[0140] Compound 39: N-((Z)-1'-(benzyloxy)-4'-(2-naphthyl)-5'-oxo-2'-phenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0141]

[0142] Pale yellow solid, yield: 88%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.56 (s, 1H), 7.73 (d, J = 8.4Hz, 2H), 7.64 (d, J = 8.4Hz, 1H), 7.42-7.40 (m, 2H),7.39-7.37(m,2H),7.36-7.32(m,7H),7.28-7.24(m,2H),7.21(d,J=8.4Hz,2H),7.15(t,J=7.2Hz ,1H),7.04(d,J=7.2Hz,2H),6.79(t,J=7.2Hz,1H),6.75(d,J=8.4Hz,1H),7.72-7.70(m,1H),5.93(d, J=7.8Hz,1H),5.33(d,J=10.2Hz,1H),5.15(s,1H),5.04(d,J=11.4Hz,1H),4.44(s,1H),2.43(s,3H). 13 C{ 1 H}NMR(151MHz,CDCl3)δ(ppm):168.9,166.9,143.6,141.2,138.1,134.8,1 34.0,132.7,132.6,129.6,129.5,129.3,129.09,129.7,128.7,128.5,128. 3,128.2,128.0,127.7,127.5,127.2,126.8,126.7,126.0,125.7,125.5,12 5.2,123.4,110.8,77.2,66.0,60.3,52.3,21.5.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 41 H 33 N3O4SNa + :686.2084,found:686.2084.

[0143] Compound 40: N-((Z)-1'-ethoxy-5'-oxo-2',4'-diphenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)-4-methylbenzenesulfonamide

[0144]

[0145] White solid, yield: 83%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.57 (s, 1H), 7.77 (d, J = 8.4Hz, 2H), 7.41-7.35 (m, 5H), 7.16 (t, J = 7.2Hz, 1H), 7.06-7.03 (m, 3H), 6.80-6.74 (m, 4H), 6.51(d,J=7.2Hz,2H),5.81(d,J=7.8Hz,1H),5.13(s,1H),4.28-4.23(m, 1H), 4.20 (s, 1H), 4.18-4.14 (m, 1H), 2.50 (s, 3H), 1.37 (t, J = 6.6Hz, 3H). 13 C{ 1 H}NMR(151MHz, CDCl3)δ(ppm):168.9,167.2,143.7,141.2,138.0,134.1,130.3,129.5,129.3,129.1,128.8,127.9,1 27.7,127.6,127.0,125.7,125.2,123.4,110.7,77.2,70.6,65.7,60.0,52.8,21.6,14.0.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 32 H 29 N3O4SNa + :574.1771,found:574.1773.

[0146] Compound 41: 4-Methyl-N-((Z)-5'-oxo-1'-phenoxy-2',4'-diphenylspiro[indoline-3,3'-pyrrolline]-2-ylidene)benzenesulfonamide

[0147]

[0148] Yellow solid, yield: 75%. 1H NMR (600MHz, CDCl3) δ (ppm): 9.72 (s, 1H), 7.78 (d, J = 8.4Hz, 2H), 7.59 (d, J = 7.8Hz, 2H ),7.44-7.36(m,6H),7.35(d,J=8.4Hz,2H),7.18(t,J=8.4Hz,1H),7.12-7.09(m,2H), 7.02(t,J=7.8Hz,1H),6.82(d,J=7.8Hz,1H),6.76(t,J=7.2Hz,1H),6.72-6.70(m,2H) ,6.51(d,J=7.8Hz,2H),5.83(d,J=7.8Hz,1H),5.33(s,1H),4.36(s,1H),2.50(s,3H). 13 C{ 1 H}NMR(151MHz, CDCl3)δ(ppm):169.0,168.8,158.2,143.8,141.3,137.9,133.4,130.1,129.7,129.6,129.3,129.1,12 8.8,128.0,127.7,127.1,126.0,125.2,123.6,123.4,114.0,110.8,66.3,60.3,52.3,21.6.HRMS(ESI-TOF)m / z:[M+Na] + Calculated for C 36 H 29 N3O4SNa + :622.1771,found:622.1780.

[0149] Example 2. Preparation of compound A by changing the alkali

[0150] By replacing cesium carbonate in Example 1 with potassium carbonate, A was obtained in almost the same yield.

[0151] Example 3. Preparation of compound A by changing the solvent

[0152] A was obtained in a slightly lower yield by replacing tetrahydrofuran with acetonitrile in Example 1.

[0153] Experimental Example 1: Study on Antibacterial Activity

[0154] The microbroth 2-fold dilution method recommended by the Clinical and Laboratory Standards Institute (CLSI) antimicrobial susceptibility testing procedure (M02-A11, M07-A9, and M11-A8) was used to determine the susceptibility of pyrrolidone 2-indolineimine spirocyclic compound A to methicillin-resistant Staphylococcus aureus (MRSA), susceptible Staphylococcus surfaceus (MSSE), and non-enzyme-producing Escherichia coli (E. coli). - The minimum inhibitory concentration (MIC) of compounds 4, 17, 20, and 38 was determined. The results showed that compounds 4, 17, 20, and 38 were effective against non-enzyme-producing *Escherichia coli* (E. coli). - All three compounds exhibited good antibacterial activity. Specifically, compounds 4, 20, and 38 all had a MIC value of 64 μg·mL against non-enzyme-producing *Escherichia coli*. -1 The MIC of compound 17 against non-enzyme-producing Escherichia coli is 8 μg·mL. -1 It has a good antibacterial effect.

[0155] The foregoing description illustrates and describes several preferred embodiments of the invention. However, as previously stated, it should be understood that the invention is not limited to the forms disclosed herein and should not be construed as excluding other embodiments. It can be used in various other combinations, modifications, and environments, and can be altered within the scope of the inventive concept described herein through the foregoing teachings or techniques or knowledge in related fields. Any modifications and variations made by those skilled in the art that do not depart from the spirit and scope of the invention should be within the protection scope of the appended claims.

Claims

1. A pyrrolidone 2-indolinimine spiro compound, characterized by, The compound has the following structural formula: In the above chemical structural formula: R 1 Selected from any one of the atoms or groups of hydrogen, chlorine, and methoxy; R 2 Selected from any one of the following groups: phenyl, halogen-substituted phenyl, methyl-substituted phenyl, methoxy-substituted phenyl, naphthyl, pyridyl, cyclopentyl, butyl, ester; R 3 Selected from any one of hydrogen, allyl, or other atoms or groups; R 4 Selected from any one of the groups selected from phenyl and substituted phenyl, naphthyl, and pyridyl; R 5 It is selected from any one of the groups, phenyl and ethyl.

2. The pyrrolidone 2-indolineimine spirocyclic compound according to claim 1, characterized in that, The compound is selected from one of the following structural formulas:

3. Process for the preparation of a compound according to claim 1 or 2, characterized in that, Includes the following steps: Benzylindoline-2-imine (B) and 2-chloro-2-arylacetylhydroxylamine (C) are dissolved in an organic solvent, and a base is added to induce a cyclization reaction. After separation and purification, A is obtained.

4. The method of claim 3, wherein: The base used is one or more of the following: triethylamine (TEA), diisopropylethylamine (DIPEA), DBU (1,8-diazabicyclo[5,4,0]undec-7-ene), DABCO (1,4-diazabicyclo[2,2,2]octane), sodium carbonate, potassium carbonate, cesium carbonate, sodium phosphate, and potassium phosphate; the organic solvent used is one or more of the following: acetonitrile, dichloromethane, chloroform, tetrahydrofuran, ethylene glycol dimethyl ether, and methyl tert-butyl ether.

5. The method of claim 3, wherein: The molar ratio of benzylidene indoline-2-imine (B) to 2-chloro-2-arylacetylhydroxylamine (C) is 3:1 to 1:3; the amount of base used is 1-3 eq.

6. The preparation method according to claim 3, characterized in that: The reaction temperature is -20℃ to 50℃.

7. The pyrrolidine 2-indolinimine spiro compound of claim 1 or 2, wherein The compound is selected from the following for the preparation of drugs against non-enzyme-producing Escherichia coli:

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