Pyrrolo [2, 3-c] pyrazole compound as well as preparation method and application thereof

Abstract

The invention discloses a pyrrolo [2, 3-c] pyrazole compound as well as a preparation method and application thereof. The pyrrolo [2, 3-c] pyrazole compound has a structural formula as shown in a formula I: # imgabs0. The invention provides the pyrrolo [2, 3-c] pyrazole compound with a novel structure, and the compound has anti-tumor activity, especially for colon cancer, breast cancer, prostatic cancer and leukemia.

Description

Technical Field

[0001] The present invention relates to the technical field of small molecule compounds, and in particular to a pyrrolo[2,3-c]pyrazole compound and a preparation method and application thereof. Background Art

[0002] Polycyclic nitrogen-containing heterocyclic skeletons are widely present in natural products and active pharmaceutical ingredients, serving as core building blocks for biological activity. Compounds containing this type of skeleton, particularly pyrrolo[2,3-c]pyrazole structures, exhibit significant antibacterial activity. For example, the Shawkat group demonstrated in vitro antibacterial activity against Bacillus cereus and Escherichia coli, with inhibition zones ranging from 19 to 41 mm. Compounds also exhibited in vitro antifungal activity against Aspergillus flavus and Stachybotrys atra, with inhibition zones ranging from 7 to 34 mm. Notably, their activity was similar to or even slightly higher than that of the standard drug tioconazole. For patients requiring androgen receptor antagonist therapy, compound A3 could be used as a tissue-selective androgen receptor modulator, demonstrating similar efficacy to androgen receptor antagonist carboxamides.

[0003]

[0004] Given the medicinal value of the core skeleton of this type of compound, the development of such pyrazolopyrrole structures is of great significance. Summary of the Invention

[0005] The present invention aims to solve at least one of the technical problems existing in the prior art. To this end, in a first aspect, the present invention provides a pyrrolo[2,3-c]pyrazole compound having anti-tumor activity.

[0006] The second aspect of the present invention also provides a method for preparing a pyrrolo[2,3-c]pyrazole compound.

[0007] The third aspect of the present invention further provides an application of a pyrrolo[2,3-c]pyrazole compound.

[0008] According to the first aspect of the present invention, a pyrrolo[2,3-c]pyrazole compound is provided; it has the structural formula shown in Formula I:

[0009]

[0010] Wherein, R1 is selected from C 1～6 Alkyl, naphthyl, isoquinolyl, phenyl or C 1～6 Alkyl, C 1～6Alkoxy, halogen, nitro, C 2～10 an ester-substituted phenyl group;

[0011] R2 is selected from H, C 1～6 Alkyl, phenyl;

[0012] R3 is selected from C 1～6 Alkyl, naphthyl, phenyl or C 1～6 Alkyl, C 1～6 haloalkyl, C 1～6 Alkoxy, halogen-substituted phenyl;

[0013] R4, R5 are independently selected from H, C 1～6 Alkyl, halogen.

[0014] According to a preferred embodiment of the present invention, R1 is selected from C 3～6 Cycloalkyl, naphthyl, isoquinolyl, phenyl or C 1～3 Alkyl, C 1～3 Alkoxy, F, Cl, nitro, C 2～10 Phenyl substituted with an ester group.

[0015] According to a preferred embodiment of the present invention, R2 is selected from H, C 1～3 Alkyl, phenyl.

[0016] According to a preferred embodiment of the present invention, R3 is selected from C 3～6 Cycloalkyl, naphthyl, phenyl or C 1～3 Alkyl, C 1～3 Fluorinated alkyl, C 1～3 Alkoxy, F, Cl, Br substituted phenyl.

[0017] According to a preferred embodiment of the present invention, the pyrrolo[2,3-c]pyrazole compound is selected from the following structural formula:

[0018]

[0019] The pyrrolo[2,3-c]pyrazole compound provided according to the embodiment of the present invention has at least the following beneficial effects:

[0020] The present invention provides novel pyrrolo[2,3-c]pyrazole compounds, which have anti-tumor activity, especially against colon cancer, breast cancer, prostate cancer and blood cancer.

[0021] According to a second aspect of the present invention, a method for preparing a pyrrolo[2,3-c]pyrazole compound is provided, comprising the following steps:

[0022] S1. Mixing compound 2-1, compound 2-2, and a solvent to react under blue light irradiation;

[0023] S2. After step S1 is completed, compound 3-3 and a catalyst are added to the system and the reaction is continued;

[0024] Among them, the structural formulas of compound 2-1, compound 2-2 and compound 3-3 are as follows:

[0025]

[0026] The definitions of R1, R2, R3, R4 and R5 are consistent with those in the specification of the present invention.

[0027] According to a preferred embodiment of the present invention, the Bronsted acid catalyst includes at least one of p-toluenesulfonic acid monohydrate, diphenyl phosphate, trifluoroacetic acid, binaphthol phosphate, rac camphorsulfonic acid, and squaric acid.

[0028] According to a preferred embodiment of the present invention, the solvent includes at least one of a benzene solvent, a chlorinated solvent, and an ether solvent.

[0029] According to a preferred embodiment of the present invention, the benzene solvent includes chlorobenzene and toluene.

[0030] According to a preferred embodiment of the present invention, the chlorinated solvent includes dichloromethane and dichloroethane.

[0031] According to a preferred embodiment of the present invention, the ether solvent includes ethylene glycol dimethyl ether.

[0032] According to a preferred embodiment of the present invention, in step S2, the reaction temperature is 40-80°C.

[0033] According to a preferred embodiment of the present invention, in step S2, the reaction time is 6 to 48 hours.

[0034] According to a preferred embodiment of the present invention, the molar ratio of compound 2-1, compound 2-2 and compound 3-3 is (1-2): (1-2):1.

[0035] The method for preparing pyrrolo[2,3-c]pyrazole compounds provided in accordance with an embodiment of the present invention has at least the following beneficial effects:

[0036] The present invention uses compound 2-1, compound 2-2 and compound 3-3 as raw materials and can prepare them through a two-step one-pot method. The method is simple to operate, has good substrate universality and high yield.

[0037] The third aspect of the present invention provides a use of the above-mentioned pyrrolo[2,3-c]pyrazole compound in the preparation of a drug for treating and / or preventing anti-tumor.

[0038] According to a preferred embodiment of the present invention, the tumor includes colon cancer, breast cancer, prostate cancer, and blood cancer.

[0039] Definitions and General Terms

[0040] “C 1-6 "alkyl" means an alkyl group having a total carbon number of 1 to 6, including C 1-6 Straight chain alkyl, C 1-6 Branched alkyl and C 3-6 The cycloalkyl group may be, for example, a straight-chain alkyl group having 1, 2, 3, 4, 5 or 6 carbon atoms, a branched-chain alkyl group having 1, 2, 3, 4, 5 or 6 carbon atoms, or a cycloalkyl group having 3, 4, 5 or 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, cyclopropyl, methylcyclopropyl, ethylcyclopropyl, cyclopentyl, methylcyclopentyl, cyclohexyl, etc. 1-3 The "alkyl group" has a similar explanation, except that the number of carbon atoms is different.

[0041] “C 1-6 "alkoxy" means an alkoxy group having a total carbon number of 1 to 6, including C 1-6 Straight chain alkoxy, C 1-6 Branched alkoxy and C 2-6 The cycloalkoxy group may be, for example, a straight chain alkoxy group having 1, 2, 3, 4, 5 or 6 carbon atoms, a branched chain alkoxy group having 1, 2, 3, 4, 5 or 6 carbon atoms, or a cycloalkoxy group having 2, 3, 4, 5 or 6 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, etc. 1-3 The "alkoxy group" has a similar explanation, except that the number of carbon atoms is different.

[0042] “C 1～6 The alkyl halide and C 1-6 The definition of "alkyl" is similar, except that "C 1～6 Any one H atom in the "haloalkyl" is replaced by any halogen.

[0043] The "halogen" includes any one or two or more of fluorine, chlorine, bromine and iodine.

[0044] “C 2～10 The term "ester group" refers to an ester group having 2 to 10 carbon atoms, and representative examples include methyl formate, ethyl formate, ethyl acetate, methyl acetate, and the like.

[0045] Other features and advantages of the present invention will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by practice of the present invention. BRIEF DESCRIPTION OF THE DRAWINGS

[0046] The above and / or additional aspects and advantages of the present invention will become apparent and readily understood from the following description of the embodiments with reference to the accompanying drawings, in which:

[0047] Figure 1 The IC of the pyrrolo[2,3-c]pyrazole compound prepared in the embodiment of the present invention on cancer cells is 50 picture. DETAILED DESCRIPTION

[0048] The following are specific embodiments of the present invention, and the technical solutions of the present invention are further described in conjunction with the embodiments, but the present invention is not limited to these embodiments.

[0049] Unless otherwise specified, the reagents, methods and equipment used in the present invention are conventional reagents, methods and equipment in the art.

[0050] Example 1

[0051] This example provides a pyrrolo[2,3-c]pyrazole compound 3-4a, the reaction equation and preparation method of which are as follows:

[0052]

[0053] Phenylacetylene 2-1a (0.4 mmol) and benzoquinone 2-2a (0.3 mmol) were used as template substrates, and acetonitrile was used as the reaction solvent. The reaction was carried out at room temperature under 70 W blue light for 4 h. Subsequently, compound 3-1a (0.2 mmol) and diphenyl phosphate (20 mol%) were added at room temperature, and the temperature was then raised to 60 ° C for a two-step one-pot reaction for 12 h to obtain pyrrolo[2,3-c]pyrazole compound 3-4a.

[0054] The data are as follows:

[0055] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white solid,mp253-254℃,65.7mg,90%yield). 1H NMR (500MHz, DMSO) δ11.41(s,1H),9.38(s,1H),7.86(d,J=7.7Hz,2H),7.48(dd,J=8.4,7.6Hz,2H),7.40(d,J=7.2Hz,2H),7. 33(t,J=7.6Hz,2H),7.25(t,J=7.3Hz,1H),7.19(t,J=7.4Hz,1H),7.13(d,J=8.5Hz,2H),6.74(d,J=8.5Hz,2H),2.28(s,3H). 13 C{1H}NMR(126MHz,DMSO)δ155.8,140.1,139.2,139.0,133.2,131.2,130.5, 129.3,128.6,128.2,126.7,125.1,123.9,117.1,117.0,115.3,111.2,13.9.

[0056] Example 2

[0057] This example provides a pyrrolo[2,3-c]pyrazole compound 3-5a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-1a is as follows:

[0058] The structural formula and data obtained are as follows:

[0059]

[0060] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,52.3mg,69%yield). 1 HNMR (500MHz, Acetone) δ10.43(s,1H),8.36(s,1H),7.87(d,J=7.7Hz,2H),7.46(dd,J=8.4,7.5Hz,2H),7.31(s,1H ),7.24(d,J=8.5Hz,2H),7.21–7.12(m,3H),7.05(d,J=7.3Hz,1H),6.85(d,J=8.5Hz,2H),2.35(s,3H),2.26(s,3H). 13C{1H}NMR(126MHz,Acetone)δ156.9,141.4,140.6,140.5,138.4,134.4,132.2,131.6,130.1,129. 7,128.9,128.2,127.1,126.5,124.7,118.5,118.0,116.0,112.8,21.4,14.2.HRMS(ESI)m / z:[M+H] + Calcd for C 25 H 22 N3O 380.1757; Found 380.1763.

[0061] Example 3

[0062] This example provides a pyrrolo[2,3-c]pyrazole compound 3-6a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-1a is as follows

[0063] The structural formula and data obtained are as follows:

[0064]

[0065] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,63.7mg,84%yield). 1 HNMR (500MHz, Acetone) δ10.41(s,1H),8.43(s,1H),7.87(d,J=7.8Hz,2H),7.46(t,J=8.0Hz,2H),7.32(d,J=8.1Hz,2H ),7.23(t,J=5.6Hz,2H),7.17(t,J=7.4Hz,1H),7.11(d,J=7.9Hz,2H),6.84(d,J=8.5Hz,2H),2.34(s,3H),2.31(s,3H). 13 C{1H}NMR(126MHz,Acetone)δ156.9,141.3,140.6,140.5,137.1,132.2,131.6,130.1,1 29.7,129.1,127.1,124.7,118.5,118.0,116.1,112.4,21.1,14.2.HRMS(ESI)m / z:[M+H] + Calcd for C 25 H 22N3O 380.1757; Found 380.1761.

[0066] Example 4

[0067] This example provides a pyrrolo[2,3-c]pyrazole compound 3-7a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-1a is as follows

[0068] The structural formula and data obtained are as follows:

[0069]

[0070] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,45.8mg,58%yield). 1 H NMR (500MHz, Acetone) δ10.43(s,1H),8.38(s,1H),7.87(d,J=8.3Hz,2H),7.46(t,J=8.0Hz,2H),7.25(d,J=8.5Hz,2H),7. 22–7.15(m,2H),7.00(dd,J=4.0,1.7Hz,2H),6.86(d,J=8.5Hz,2H),6.79(dd,J=7.9,2.0Hz,1H),3.69(s,3H),2.33(s,3H). 13 C{1H}NMR(126MHz,Acetone)δ160.5,157.0,141.3,140.63,140.56,135.7,132.0,131.7,130.1,130 .0,127.0,124.8,121.4,118.6,118.0,116.1,114.5,113.2,113.1,55.3,14.2.HRMS(ESI)m / z:[M+H] + Calcd for C 25 H 22 N3O2 396.1707; Found 396.1712.

[0071] Example 5

[0072] This example provides a pyrrolo[2,3-c]pyrazole compound 3-8a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-1a is as follows:

[0073] The structural formula and data obtained are as follows:

[0074]

[0075] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,63.9mg,72%yield). 1 HNMR(500MHz,Acetone)δ10.54(s,1H),8.46(s,1H),7.89–7.80(m,2H),7.47(dt,J=8.3,3.7Hz,4H),7 .37(d,J=8.5Hz,2H),7.23(d,J=8.5Hz,2H),7.19(t,J=7.4Hz,1H),6.86(d,J=8.5Hz,2H),2.32(s,3H). 13 C{1H}NMR(126MHz,Acetone)δ157.1,141.6,140.6,140.5,133.7,132.1,131.6,130.9,13 0.8,130.1,126.6,124.9,120.7,118.6,118.1,116.3,113.6,14.1.HRMS(ESI)m / z:[M+H] + Calcd for C 24 H 19 BrN3O445.0740; Found 445.0743.

[0076] Example 6

[0077] This example provides a pyrrolo[2,3-c]pyrazole compound 3-9a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-1a is as follows:

[0078] The structural formula and data obtained are as follows:

[0079]

[0080] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,54.2mg,68%yield). 1HNMR (500MHz, DMSO) δ11.44(s,1H),9.42(s,1H),7.85(dd,J=8.6,0.9Hz,2H),7.49(dd,J=8.5,7.5Hz,2H ),7.39(s,4H),7.20(dd,J=10.6,4.2Hz,1H),7.13(d,J=8.6Hz,2H),6.76(d,J=8.6Hz,2H),2.27(s,3H). 13 C{1H}NMR(126MHz,DMSO)δ156.0,140.2,139.3,139.0,132.0,131.1,130.5,130.0,129 .8,129.4,128.2,124.8,124.0,117.2,117.0,115.4,111.8,13.8.HRMS(ESI)m / z:[M+H] + Calcd for C 24 H 19 ClN3O400.1211; Found 400.1217.

[0081] Example 7

[0082] This example provides a pyrrolo[2,3-c]pyrazole compound 3-10a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-1a is as follows:

[0083] The structural formula and data obtained are as follows:

[0084]

[0085] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,73.5mg,96%yield). 1 HNMR (500MHz, DMSO) δ11.43(s,1H),9.41(s,1H),7.85(d,J=7.7Hz,2H),7.48(t,J=8.0Hz,2H),7.42(dd,J =8.8,5.6Hz,2H),7.18(dd,J=11.7,6.1Hz,3H),7.12(d,J=8.5Hz,2H),6.75(d,J=8.5Hz,2H),2.28(s,3H). 13 C{1H}NMR(126MHz,DMSO)δ161.09(J C-F=244.2Hz),155.9,140.1,139.2,139.1,130.6,130.53,130.46,130.2,12 9.7,129.4,125.0,124.0,117.0,116.9,115.4,115.2,115.0,111.2,13.9. 19 FNMR(471MHz,DMSO)δ-115.23.HRMS(ESI)m / z:[M+H] + Calcd for C 24 H 19 FN3O 384.1507; Found384.1511.

[0086] Example 8

[0087] This example provides a pyrrolo[2,3-c]pyrazole compound 3-11a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-1a is as follows:

[0088] The structural formula and data obtained are as follows:

[0089]

[0090] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,62.0mg,81%yield). 1 HNMR (500MHz, Acetone) δ10.51(s,1H),8.46(s,1H),7.87(d,J=7.8Hz,2H),7.46(t,J=8.0Hz,2H ),7.34–7.23(m,4H),7.22–7.13(m,2H),7.03–6.93(m,1H),6.89(d,J=8.5Hz,2H),2.33(s,3H). 13 C{1H}NMR(126MHz,Acetone)δ163.44(J C-F =242.9Hz),157.2,141.5,140.7,140.5,136.8,136.7,131.7,130.9,130.8,130.6,130.6,1 30.1,126.6,124.90,124.87,118.7,118.1,116.3,115.4,115.2,114.0,113.9,113.8,14.1. 19F NMR(471MHz,Acetone)δ-114.64.HRMS(ESI)m / z:[M+H] + Calcd for C 24 H 19 FN3O384.1507; Found 384.1512.

[0091] Example 9

[0092] This example provides a pyrrolo[2,3-c]pyrazole compound 3-12a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-1a is as follows:

[0093] The structural formula and data obtained are as follows:

[0094]

[0095] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,68.2mg,89%yield). 1 HNMR(500MHz,Acetone)δ10.57(s,1H),8.32(s,1H),7.93–7.80(m,2H),7.52–7.42 (m,2H),7.41–7.31(m,2H),7.24–7.06(m,5H),6.80(d,J=8.6Hz,2H),2.40(s,3H). 13 C{1H}NMR(126MHz,Acetone)δ161.11(J C-F =247.3Hz),156.8,141.6,140.6,140.5,133.4,133.4,131.0,130.31,130.25,130.1,126.9, 125.4,124.93,124.90,124.8,122.3,122.2,117.8,117.6,116.7,116.5,116.0,114.8,14.5. 19 F NMR(471MHz,Acetone)δ-114.30.HRMS(ESI)m / z:[M+H] + Calcd for C 24 H 19 FN3O 384.1507; Found384.1511.

[0096] Example 10

[0097] This example provides a pyrrolo[2,3-c]pyrazole compound 3-13a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-1a is as follows:

[0098] The structural formula and data obtained are as follows:

[0099]

[0100] (eluent:petroleum ether / ethyl acetate 3:1 to 2:1,12h,black solid,58.2mg,71%yield). 1 H NMR (500MHz, Acetone) δ10.72(s,1H),8.54(s,1H),8.13(d,J=8.8Hz,2H),7.85(d,J=8.2Hz,2H),7.66(d,J=8.8 Hz,2H),7.48(t,J=7.9Hz,2H),7.27(d,J=8.4Hz,2H),7.21(t,J=7.4Hz,1H),6.91(d,J=8.4Hz,2H),2.32(s,3H). 13 C{1H}NMR(126MHz,Acetone)δ157.6,146.4,142.2,141.1,140.3,131.8,130.2,129.89 ,128.89,126.1,125.2,124.3,119.3,118.2,116.5,116.4,14.0.HRMS(ESI)m / z:[M+H] + Calcd for C 24 H 19 N4O3 411.1452; Found 411.1457.

[0101] Example 11

[0102] This example provides a pyrrolo[2,3-c]pyrazole compound 3-14a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-1a is as follows:

[0103] The structural formula and data obtained are as follows:

[0104]

[0105] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,57.5mg,68%yield). 1 HNMR(500MHz,DMSO)δ11.53(s,1H),9.47(s,1H),7.87(t,J=7.6Hz,4H),7.63–7.38(m,4H),7 .21(t,J=7.4Hz,1H),7.15(d,J=8.5Hz,2H),6.78(d,J=8.5Hz,2H),3.84(s,3H),2.28(s,3H). 13 C{1H}NMR(126MHz,DMSO)δ166.0,156.2,140.7,139.5,138.9,137.9,130.6,129.9,129.4,129 .0,128.1,127.1,124.7,124.1,117.6,117.1,115.5,113.2,52.1,13.8.HRMS(ESI)m / z:[M+H] + Calcd for C 26 H 22 N3O3424.1656;Found 424.1660.

[0106] Example 12

[0107] This example provides a pyrrolo[2,3-c]pyrazole compound 3-15a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-1a is as follows:

[0108] The structural formula and data obtained are as follows:

[0109]

[0110] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,21.6mg,26%yield). 1HNMR (500MHz, Acetone) δ10.61(s,1H),8.02(s,1H),7.90(dd,J=8.6,1.0Hz,2H),7.87–7.82(m,1H),7.82–7.77(m,1H),7.75(d,J=8.6 Hz,1H),7.47(ddd,J=6.5,4.8,3.3Hz,5H),7.33–7.24(m,2H),7.19(t,J=7.4Hz,1H),6.86(d,J=8.6Hz,2H),6.67(s,1H),2.38(s,3H). 13 C{1H}NMR(126MHz,Acetone)δ157.0,151.1,141.6,140.7,140.6,134.5,133.2,132.11,132.09,131.7,130.1,128.6,1 28.4,128.3,127.7,127.3,127.1,126.9,126.6,124.8,118.6,118.0,116.6,116.2,113.5,14.3.HRMS(ESI)m / z:[M+H] + Calcd for C 28 H 22 N3O 416.1757; Found 416.1761.

[0111] Example 13

[0112] This example provides a pyrrolo[2,3-c]pyrazole compound 3-16a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-1a is as follows:

[0113] The structural formula and data obtained are as follows:

[0114]

[0115] (eluent:petroleum ether / ethyl acetate 2:1 to 1:1,12h,yellow solid,25mg,30%yield). 1H NMR (500MHz, DMSO) δ11.60(s,1H),9.44(s,1H),8.85(d,J=2.7Hz,1H),8.31(d,J=8.0Hz,1H),8.08(s,1H),7.88(dd,J=8.2,4.5Hz,3H),7. 62(dd,J=8.8,1.7Hz,1H),7.52(dt,J=14.2,6.4Hz,3H),7.22(t,J=7.3Hz,1H),7.17(d,J=8.4Hz,2H),6.75(d,J=8.4Hz,2H),2.31(s,3H). 13 C{1H}NMR(126MHz,DMSO)δ156.1,150.2,146.7,140.4,139.4,139.0,135.8,131.4,130.6,130.5,129 .4,128.4,128.0,126.6,124.8,124.1,121.8,117.2,117.0,115.4,112.3,13.9.HRMS(ESI)m / z:[M+H] + Calcd for C 27 H 21 N4O417.1710;Found417.1712.

[0116] Example 14

[0117] This example provides a pyrrolo[2,3-c]pyrazole compound 3-17a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-1a is as follows:

[0118] The structural formula and data obtained are as follows:

[0119]

[0120] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,22.4mg,34%yield). 1HNMR (500MHz, DMSO) δ10.71(s,1H),9.34(s,1H),7.77(d,J=7.7Hz,2H),7.46(t,J=8.0Hz,2H),7.35(d,J=8.5Hz,2H),7.1 7(t,J=7.4Hz,1H),6.83(d,J=8.5Hz,2H),2.29(s,3H),2.09–1.99(m,1H),0.88–0.80(m,2H),0.72(dd,J=5.3,1.9Hz,2H). 13 C{1H}NMR(126MHz,DMSO)δ155.4,139.1,138.8,138.4,133.0,130.0,129.3,1 25.7,123.8,116.9,115.5,115.1,111.4,14.2,8.5,7.5.HRMS(ESI)m / z:[M+H] + Calcd for C 21 H 20 N3O 330.1601; Found 330.1604.

[0121] Example 15

[0122] This example provides a pyrrolo[2,3-c]pyrazole compound 3-18a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-2a is as follows:

[0123] The structural formula and data obtained are as follows:

[0124]

[0125] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,64.4mg,85%yield). 1HNMR(500MHz,DMSO)δ11.37(s,1H),9.24(s,1H),7.85(dd,J=8.6,0.9Hz,2H) ,7.48(dd,J=8.5,7.5Hz,2H),7.43–7.37(m,2H),7.33(dd,J=10.4,4.8Hz,2H ),7.24(dd,J=8.2,6.4Hz,1H),7.19(t,J=7.4Hz,1H),7.05(d,J=1.7Hz,1H), 6.91(dd,J=8.1,2.0Hz,1H),6.72(d,J=8.2Hz,1H),2.28(s,3H),2.08(s,3H). 13 C{1H}NMR(126MHz,DMSO)δ153.9,140.1,139.3,139.1,133.3,131.7,131.1,129.3,128.5,128.1, 127.7,126.6,125.1,123.9,123.7,117.2,116.9,114.7,111.4,16.1,13.9.HRMS(ESI)m / z:[M+H] + Calcd for C 25 H 22 N3O 380.1757; Found 380.1762.

[0126] Example 16

[0127] This example provides a pyrrolo[2,3-c]pyrazole compound 3-19a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-2a is as follows:

[0128] The structural formula and data obtained are as follows:

[0129]

[0130] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,60.0mg,75%yield). 1HNMR (500MHz, DMSO) δ11.53(s,1H),10.15(s,1H),7.87(d,J=7.8Hz,2H),7.48(t,J=8.0Hz,2H),7.45–7.39(m,2H),7.35(dd,J =15.1,7.2Hz,2H),7.29(t,J=7.3Hz,1H),7.25–7.15(m,2H),7.11(dd,J=8.3,2.1Hz,1H),6.96(d,J=8.3Hz,1H),2.31(s,3H). 13 C{1H}NMR(126MHz,DMSO)δ151.4,140.2,139.1,139.0,132.8,131.7,130.3,129.3,129.1,128 .7,128.3,127.0,126.7,124.0,119.5,117.0,116.8,116.7,109.7,13.9.HRMS(ESI)m / z:[M+H] + Calcd for C 24 H 19 ClN3O 400.1211; Found 400.1217.

[0131] Example 17

[0132] This example provides a pyrrolo[2,3-c]pyrazole compound 3-20a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-3a is as follows:

[0133] The structural formula and data obtained are as follows:

[0134]

[0135] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,53.0mg,70%yield). 1 H NMR(500MHz,Acetone)δ10.39(s,1H),8.37(s,1H),7.75(d,J=8.5Hz,2H),7.46– 7.36(m,2H),7.33–7.15(m,7H),6.84(d,J=8.5Hz,2H),2.35(s,3H),2.33(s,3H). 13C{1H}NMR(126MHz,Acetone)δ156.9,141.4,140.0,138.4,134.5,134.3,132.0,131.6,130. 5,129.2,129.0,127.4,127.1,118.4,118.0,116.1,112.8,20.8,14.2.HRMS(ESI)m / z:[M+H] + Calcd for C 25 H 22 N3O 380.1757; Found 380.1763.

[0136] Example 18

[0137] This example provides a pyrrolo[2,3-c]pyrazole compound 3-21a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-3a is as follows:

[0138] The structural formula and data obtained are as follows:

[0139]

[0140] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,53.7mg,68%yield). 1 H NMR (500MHz, DMSO) δ11.31(s,1H),9.37(s,1H),7.76(d,J=9.0Hz,2H),7.39(d,J=7.3Hz,2H),7.32(t,J=7.6Hz,2H), 7.23(t,J=7.3Hz,1H),7.13(d,J=8.5Hz,2H),7.04(d,J=9.0Hz,2H),6.74(d,J=8.5Hz,2H),3.80(s,3H),2.27(s,3H). 13 C{1H}NMR(126MHz,DMSO)δ156.1,155.8,140.3,138.3,133.3,132.8,131.0,130.0,128.4, 128.2,126.6,125.3,118.8,116.8,115.3,114.5,111.2,55.4,13.8.HRMS(ESI)m / z:[M+H] + Calcd for C 25 H 22N3O2 396.1707; Found 396.1712.

[0141] Example 19

[0142] This example provides a pyrrolo[2,3-c]pyrazole compound 3-22a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-3a is as follows:

[0143] The structural formula and data obtained are as follows:

[0144]

[0145] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,75.0mg,87%yield). 1 HNMR (500MHz, Acetone) δ10.61(s,1H),8.43(s,1H),8.07(d,J=8.5Hz,2H),7.78(d,J=8.6Hz,2H),7.43(dd ,J=5.2,3.3Hz,2H),7.34–7.26(m,2H),7.23(ddd,J=6.1,4.0,1.6Hz,3H),6.92–6.78(m,2H),2.35(s,3H). 13 C{1H}NMR(126MHz,Acetone)δ157.0,143.2,142.4,141.2,134.2,132.5,131 .7,129.3,129.1,127.6,127.37,127.35,127.32,127.29,126.6,125.55(q,J C-F =32.3Hz),125.41(J C-F =270.9Hz),119.0,117.7,116.1,113.0,14.2. 19 F NMR(471MHz,Acetone)δ-62.24.HRMS(ESI)m / z:[MH] - Calcdfor C 25 H 17 F3N3O 432.1329;Found 432.1331.

[0146] Example 20

[0147] This example provides a pyrrolo[2,3-c]pyrazole compound 3-23a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-3a is as follows:

[0148] The structural formula and data obtained are as follows:

[0149]

[0150] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,66.6mg,87%yield). 1 HNMR(500MHz,Acetone)δ10.46(s,1H),8.39(s,1H),7.93–7.78(m,2H),7.49–7.36(m,2H),7 .29(t,J=7.5Hz,2H),7.23(ddd,J=10.9,5.6,3.3Hz,5H),6.85(d,J=8.5Hz,2H),2.33(s,3H). 13 C{1H}NMR(126MHz,Acetone)δ160.26(J C-F =241.5Hz),156.9,141.4,140.6,137.11,137.09,134.4,132.1,131.6,129.2, 129.1,127.5,126.9,119.83,119.76,118.5,116.7,116.5,116.1,112.9,14.2. 19 F NMR(471MHz,Acetone)δ-120.76.HRMS(ESI)m / z:[M+H] + Calcd for C 24 H 19 FN3O 384.1507; Found 384.1512.

[0151] Example 21

[0152] This example provides a pyrrolo[2,3-c]pyrazole compound 3-24a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-3a is as follows:

[0153] The structural formula and data obtained are as follows:

[0154]

[0155] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,58.3mg,73%yield). 1 HNMR (500MHz, Acetone) δ10.24(s,1H),8.45(s,1H),7.61(ddd,J=18.3,7.9,1.5Hz,2H),7.47(td,J=7.7,1 .4Hz,1H),7.44–7.36(m,3H),7.30–7.22(m,4H),7.18(t,J=7.3Hz,1H),6.86(d,J=8.5Hz,2H),2.32(s,3H). 13 C{1H}NMR(126MHz,Acetone)δ156.9,143.9,141.1,138.3,134.6,131.6,131.4,131.1,129.4,129 .3,129.1,129.0,128.63,128.58,127.3,127.2,117.2,116.1,112.6,14.1.HRMS(ESI)m / z:[M+H] + Calcd for C 24 H 19 ClN3O 400.1211; Found 400.1217.

[0156] Example 22

[0157] This example provides a pyrrolo[2,3-c]pyrazole compound 3-25a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-3a is as follows:

[0158] The structural formula and data obtained are as follows:

[0159]

[0160] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,66.2mg,83%yield). 1HNMR (500MHz, Acetone) δ10.63(s,1H),8.38(s,1H),7.89(t,J=2.0Hz,1H),7.86–7.78(m,1H),7.50–7.37(m,3H ),7.30(dd,J=10.2,4.7Hz,2H),7.26–7.20(m,3H),7.18(dd,J=8.0,1.2Hz,1H),6.89–6.80(m,2H),2.34(s,3H). 13 C{1H}NMR(126MHz,Acetone)δ157.0,141.7,141.6,141.2,135.5,134.3,132.4,131.63,131.58,12 9.3,129.1,127.6,126.8,124.5,118.8,117.5,116.12,116.10,113.0,14.2.HRMS(ESI)m / z:[M+H] + Calcd for C 24 H 19 ClN3O 400.1211; Found 400.1218.

[0161] Example 23

[0162] This example provides a pyrrolo[2,3-c]pyrazole compound 3-26a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-3a is as follows:

[0163] The structural formula and data obtained are as follows:

[0164]

[0165] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,66.2mg,83%yield). 1 HNMR(500MHz,DMSO)δ11.47(s,1H),9.38(s,1H),7.96–7.79(m,2H),7.60–7.46(m,2H),7.44–7.36(m,2H) ,7.33(t,J=7.6Hz,2H),7.25(t,J=7.3Hz,1H),7.12(d,J=8.5Hz,2H),6.74(d,J=8.5Hz,2H),2.28(s,3H). 13C{1H}NMR(126MHz,DMSO)δ155.9,140.0,139.9,137.8,133.1,131.4,130.5,129.2,128 .5,128.2,127.7,126.8,125.0,118.5,117.3,115.3,111.3,13.8.HRMS(ESI)m / z:[M+H] + Calcd for C 24 H 19 ClN3O400.1211; Found 400.1215.

[0166] Example 24

[0167] This example provides a pyrrolo[2,3-c]pyrazole compound 3-27a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-3a is as follows:

[0168] The structural formula and data obtained are as follows:

[0169]

[0170] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,69.4mg,79%yield). 1 HNMR(500MHz,DMSO)δ11.48(s,1H),9.38(s,1H),7.91–7.76(m,2H),7.70–7.57(m,2H),7.44–7.37(m,2 H),7.33(t,J=7.6Hz,2H),7.26(d,J=7.3Hz,1H),7.12(d,J=8.5Hz,2H),6.83–6.61(m,2H),2.28(s,3H). 13 C{1H}NMR(126MHz,DMSO)δ155.9,140.0,139.9,138.2,133.1,132.1,131.4,130.5,128 .6,128.2,126.8,125.0,118.8,117.3,115.7,115.3,111.3,13.9.HRMS(ESI)m / z:[M+H] + Calcd for C 24 H 19 BrN3O445.0740; Found 440.0745.

[0171] Example 25

[0172] This example provides a pyrrolo[2,3-c]pyrazole compound 3-28a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-3a is as follows:

[0173] The structural formula and data obtained are as follows:

[0174]

[0175] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,61.4mg,74%yield). 1 H NMR (500MHz, DMSO) δ11.58(s,1H),9.40(s,1H),8.30(s,1H),8.16(dd,J=8.9,2.0Hz,1H),8.01(dd,J=16.3,8.6Hz,2H),7.93(d,J=8.1Hz,1H),7 .55(t,J=7.4Hz,1H),7.50–7.41(m,3H),7.37(t,J=7.6Hz,2H),7.28(t, J=7.3Hz,1H),7.16(d,J=8.4Hz,2H),6.76(d,J=8.4Hz,2H),2.34(s,3H). 13 C{1H}NMR(126MHz,DMSO)δ155.9,140.2,139.6,136.6,133.7,133.2,131.4,130.5,130.1,129.2,128.7,128. 3,127.7,127.4,126.82,126.79,125.1,124.9,117.7,117.3,115.3,112.3,111.3,13.9.HRMS(ESI)m / z:[M+H] + Calcd for C 28 H 22 N3O 416.1757; Found 416.1761.

[0176] Example 26

[0177] This example provides a pyrrolo[2,3-c]pyrazole compound 3-29a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-3a is as follows:

[0178] The structural formula and data obtained are as follows:

[0179]

[0180] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,52.7mg,71%yield). 1 HNMR (500MHz, DMSO) δ10.82(s,1H),9.31(s,1H),7.37–7.31(m,2H),7.28(dd,J=10.4,5.0Hz,2H),7.21–7.15(m,1H),7.09(d,J= 8.6Hz,2H),6.71(d,J=8.6Hz,2H),4.24–3.97(m,1H),2.15(s,3H),2.00–1.76(m,6H),1.67(d,J=12.3Hz,1H),1.48–1.15(m,3H). 13 C{1H}NMR(126MHz,DMSO)δ155.6,142.0,134.7,133.8,130.3,129.6,128.2,127.6,1 26.1,126.0,115.2,115.0,110.7,57.6,31.7,25.3,24.8,13.9.HRMS(ESI)m / z:[M+H] + Calcd for C 24 H 26 N3O 372.2070; Found 372.2075.

[0181] Example 27

[0182] This example provides a pyrrolo[2,3-c]pyrazole compound 3-30a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-3a is as follows:

[0183] The structural formula and data obtained are as follows:

[0184]

[0185] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,12h,white foamysolid,54.1mg,77%yield). 1HNMR(500MHz,DMSO)δ11.52(s,1H),9.35(s,1H),7.91(d,J=8.1Hz,2H),7.80(s,1H),7.51(dd,J=14.0,7.5Hz,4H) ,7.40(t,J=7.5Hz,2H),7.33(t,J=7.3Hz,1H),7.25(t,J=7.3Hz,1H),7.19(d,J=8.3Hz,2H),6.71(d,J=8.3Hz,2H). 13 C{1H}NMR(126MHz,DMSO)δ155.6,139.8,139.0,133.4,131.6,130.5,129.4,129.0,1 28.9,128.3,127.2,125.6,124.6,118.1,117.4,115.4,109.8.HRMS(ESI)m / z:[M+H] + Calcd for C 23 H 18 N3O 352.1444; Found 352.1448.

[0186] Example 28

[0187] This example provides a pyrrolo[2,3-c]pyrazole compound 3-31a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-3a is as follows:

[0188] The structural formula and data obtained are as follows:

[0189]

[0190] (eluent:petroleum ether / ethyl acetate 3:1 to 2:1,12h,white foamysolid,32.5mg,38%yield). 1 HNMR (500MHz, DMSO) δ11.66(s,1H),9.43(s,1H),8.00(d,J=7.8Hz,2H),7.56(t,J=7.9Hz,2H),7.49–7.42(m,2H),7.39(d,J=7. 3Hz,2H),7.30(dd,J=16.1,8.1Hz,3H),7.27–7.21(m,2H),7.19(t,J=7.3Hz,2H),7.01(d,J=8.4Hz,2H),6.71(d,J=8.5Hz,2H). 13C{1H}NMR(126MHz,DMSO)δ156.2,141.8,140.8,138.9,133.04,133.02,133.01,131.8,129.4,128.4 ,128.1,127.9,127.5,127.4,126.7,125.7,124.8,117.9,115.9,115.0,111.4.HRMS(ESI)m / z:[M+H] + Calcd for C 29 H 22 N3O 428.1757; Found 428.1761.

[0191] Example 29

[0192] This example provides a pyrrolo[2,3-c]pyrazole compound 3-32a, the preparation method of which is the same as that of Example 1, except that the structural formula of 3-1a is as follows:

[0193] The structural formula and data obtained are as follows:

[0194]

[0195] (eluent:petroleum ether / ethyl acetate 5:1 to 3:1,3h, white foamy solid, 66.5mg, 61% yield). 1 H NMR (500MHz, Acetone) δ10.60(s,1H),8.47(s,1H),7.94(d,J=8.3Hz,2H),7.86(d,J=8.2Hz,2H),7.56(d,J=8.3Hz,2H ),7.47(t,J=7.8Hz,2H),7.27(d,J=8.4Hz,2H),7.20(t,J=7.4Hz,1H),6.89(d,J=8.4Hz,2H),5.10(dd,J=7.2,2.4Hz, 1H),2.44(ddd,J=13.8,5.8,4.1Hz,1H),2.33(s,3H),2.20–2.10(m,1H),1.81(ddd,J=12.0,7.8,3.6Hz,1H),1.73(t, J=4.4Hz,1H),1.48–1.38(m,1H),1.37–1.26(m,1H),1.12(dd,J=13.6,3.6Hz,1H),0.98(s,3H),0.92(d,J=9.7Hz,6H). 13C{1H}NMR(126MHz,Acetone)δ166.6,157.3,141.9,140.8,140.5,139.0,131.7,131.0,130.1,130.0,129.2,128.6,126.6, 125.0,119.0,118.1,116.3,114.8,80.7,49.7,48.5,45.8,37.5,28.6,28.0,20.0,19.1,14.1,13.9.HRMS(ESI)m / z:[M+H] + Calcd for C 35 H 36 N3O3 546.2751; Found546.2745.

[0196] Activity test

[0197] The pyrrolo[2,3-c]pyrazole compounds prepared by the present invention are used for activity testing; the steps are as follows:

[0198] Cell lines and cell culture

[0199] MCF-7, Caco-2, Raw 264.7, and 22RV1 cell lines were cultured under standard culture conditions (37°C, 5% CO2, 95% humidity) using the following media:

[0200] MCF-7: Minimal Essential Medium (MEM; catalog #11095080, Gibco, Thermo Fisher Scientific, Waltham, MA, USA);

[0201] Caco-2: MEM medium supplemented with 1% non-essential amino acids (NEAA; catalog #11140050, Gibco);

[0202] 22RV1: RPMI 1640 medium (catalog #11875093, Gibco).

[0203] All culture media contained 10% fetal bovine serum (FBS; Gibco) and 1% penicillin / streptomycin (100 U / mL penicillin, 100 μg / mL streptomycin). Routine passage was performed when the cells reached 80-90% confluence.

[0204] Cell viability assay

[0205] The MTT assay was used to assess cell viability. The steps are briefly as follows:

[0206] 1. Seed the cells in 96-well plates (5×10 3cells, 150 μL complete medium) and allowed to adhere for 24 hours.

[0207] 2. Remove the original culture medium and add the test compound (at the indicated concentration) dissolved in fresh culture medium.

[0208] 3. After incubation for 48 hours, 10 μL of MTT solution (5 mg / mL dissolved in PBS; catalog number #HY-15924, MedChemExpress, Monmouth Junction, NJ, USA) was added to each well.

[0209] 4. Continue incubation at 37°C for 4 hours, carefully discard the supernatant, and add 100 μL of dimethyl sulfoxide (DMSO; Sigma-Aldrich, St. Louis, MO, USA) to dissolve the formazan crystals.

[0210] 5. Shake the plate on an orbital shaker for 10 minutes. Measure absorbance at 490 nm using a Bio-Rad 680 microplate reader (Hercules, CA, USA). Untreated control wells (cells alone) and blank control wells (medium alone) were included in all experiments. The inhibition rate data are shown in Table 1; cell inhibition rate = (1 - experimental group cell viability / control group cell viability) x 100%.

[0211] Table 1 Inhibition rate of pyrrolo[2,3-c]pyrazole compounds (compound concentration is 40 μM)

[0212]

[0213]

[0214] From the data in Table 1, it can be seen that the pyrrolo[2,3-c]pyrazole compounds provided by the present invention have varying degrees of inhibitory effects on colon cancer Caco-2, breast cancer MCF-7, prostate cancer 22RV1 and blood cancer Raw 264.7.

[0215] Furthermore, the present invention selects three compounds, pyrrolo[2,3-c]pyrazole compounds 3-19a, 3-22a, and 3-26a, to calculate IC 50 The result is as follows Figure 1 As shown, from Figure 1 The data show that: 3-19a (MCF-7 cell IC 50 =23.9 μM; Caco-2 cell IC 50 =22.9 μM; Raw 264.7 cell IC 50 =19.1 μM), 3-22a (MCF-7 cell IC 50 =21.8 μM; Caco-2 cell IC 50=12.4 μM; Raw 264.7 cell IC 50 =0.46 μM) and 3-26a (MCF-7 cell IC 50 =22.2 μM; Caco-2 cell IC 50 0 = 20.9 μM; Raw 264.7 cell IC 50 =12.1 μM) showed good anticancer efficacy.

[0216] The above is a detailed description of the embodiments of the present invention, but the present invention is not limited to the above embodiments. Various changes can be made within the knowledge of ordinary technicians in the relevant technical field without departing from the scope of the present invention.

Claims

1. A pyrrolo[2,3-c]pyrazole compound, characterized in that: It has the structural formula shown in Formula I: Wherein, R1 is selected from C 1～6 Alkyl, naphthyl, isoquinolyl, phenyl or C 1～6 Alkyl, C 1～6 Alkoxy, halogen, nitro, C 2～10 an ester-substituted phenyl group; R2 is selected from H, C 1～6 Alkyl, phenyl; R3 is selected from C 1～6 Alkyl, naphthyl, phenyl or C 1～6 Alkyl, C 1～6 haloalkyl, C 1～6 Alkoxy, halogen-substituted phenyl; R4, R5 are independently selected from H, C 1～6 Alkyl, halogen.

2. The pyrrolo[2,3-c]pyrazole compound according to claim 1, characterized in that R1 is selected from C 3～6 Cycloalkyl, naphthyl, isoquinolyl, phenyl or C 1～3 Alkyl, C 1～3 Alkoxy, F, Cl, nitro, C 2～10 Phenyl substituted with an ester group.

3. The pyrrolo[2,3-c]pyrazole compound according to claim 1 or 2, characterized in that R2 is selected from H, C 1～3 Alkyl, phenyl.

4. The pyrrolo[2,3-c]pyrazole compound according to claim 1 or 2, characterized in that R3 is selected from C 3～6 Cycloalkyl, naphthyl, phenyl or C 1～3 Alkyl, C 1～3 Fluorinated alkyl, C 1～3 Alkoxy, F, Cl, Br substituted phenyl.

5. The pyrrolo[2,3-c]pyrazole compound according to claim 1 or 2, characterized in that The pyrrolo[2,3-c]pyrazole compound is selected from the following structural formula:

6. A method for preparing the pyrrolo[2,3-c]pyrazole compound according to any one of claims 1 to 5, characterized in that: The steps include: S1. Mixing compound 2-1, compound 2-2 and a solvent and reacting them under blue light irradiation; S2. After step S1 is completed, compound 3-3 and a Bronsted acid catalyst are added to the system and the reaction is continued; Among them, the structural formulas of compound 2-1, compound 2-2 and compound 3-3 are as follows: 。 7. The preparation method according to claim 6, characterized in that The Bronsted acid catalyst includes at least one of p-toluenesulfonic acid monohydrate, diphenyl phosphate, trifluoroacetic acid, binaphthol phosphate, rac camphorsulfonic acid, and squaric acid.

8. The preparation method according to claim 6, characterized in that The solvent includes at least one of a benzene solvent, a chlorinated solvent, and an ether solvent; Preferably, in step S2, the reaction temperature is 40-80°C; Preferably, in step S2, the reaction time is 6 to 48 hours.

9. Use of the pyrrolo[2,3-c]pyrazole compound according to any one of claims 1 to 5 in the preparation of a drug for treating and / or preventing antitumor.

10. The use according to claim 9, characterized in that The tumors include colon cancer, breast cancer, prostate cancer, and blood cancer.

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