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Isatin derivative synthesized by N-substituted isatin hybrid quinazoline compound and application of the isatin derivative in preparation of anti-tumor drugs

A technology of hybrid quinazoline and anti-tumor drugs, which is applied in the field of preparation of anti-tumor drugs, can solve the problems of treatment impact, reduce tumor effect, etc., and achieve the effect of simple synthesis method

Active Publication Date: 2018-04-13
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These drugs have played a good role in the treatment of tumors, but after long-term use, they will produce certain side effects and drug resistance, which reduces the effect of treating tumors and affects the later treatment

Method used

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  • Isatin derivative synthesized by N-substituted isatin hybrid quinazoline compound and application of the isatin derivative in preparation of anti-tumor drugs
  • Isatin derivative synthesized by N-substituted isatin hybrid quinazoline compound and application of the isatin derivative in preparation of anti-tumor drugs
  • Isatin derivative synthesized by N-substituted isatin hybrid quinazoline compound and application of the isatin derivative in preparation of anti-tumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthetic compound A

[0039]

[0040] 0.1018g (0.3mmol) 4-(3-ethynylanilino)-6-(5-formylfuran-2-yl)quinazoline, 0.0780g (0.3mmol) (Z)-1-(diethyl Aminoethyl)-3-hydrazone indolin-2-one, 0.3mL acetic acid, 7mL ethanol and 0.1mL N,N-dimethylformamide were added to the reaction flask, and the reaction was refluxed at 79°C for 6 hours. The reaction was completed After cooling to room temperature, the solvent was removed by rotary evaporation under reduced pressure. The residue obtained was recrystallized with MeOH / THF to obtain 0.1361 g of compound A as a red solid, with a yield of 77.9%, mp 242.0-244.4°C, and structural characterization data: HRMS (C 35 H 31 N 7 O 2 )m / z[M+H] + : 582.2614 (calculated value 582.2617); 1 H NMR(600MHz, DMSO-d 6 )δ(ppm): 10.16(s,1H),9.05(s,1H),8.74(s,1H),8.69(s,1H),8.48(d,J=6.4Hz,1H),8.36(d, J = 8.2Hz, 1H), 8.09 (s, 1H), 8.03 (d, J = 7.7 Hz, 1H), 7.93 (d, J = 8.9 Hz, 1H), 7.66-7.65 (m, 1H), 7.54 7.49(m,2H),7.47(t,J=7.7Hz,1H),7.29(d,J=7.3Hz,1H),7...

Embodiment 2

[0042] Synthetic compound B

[0043]

[0044] In this example, the equimolar (Z)-1-(diethylaminoethyl)-3-hydrazone-5-fluoroindolin-2-one is used to replace (Z)-1-(二) in Example 1. Ethylaminoethyl)-3-hydrazone indolin-2-one, other steps are the same as in Example 1, to obtain 0.1340 g of compound B as a red solid, with a yield of 74.6%, mp 253.5-256.2°C, structural characterization data For: HRMS(C 35 H 30 FN 7 O 2 )m / z[M+H] + : 600.2521 (calculated value 600.2523); 1 H NMR(600MHz, DMSO-d 6 )δ(ppm): 10.11(s,1H),9.08(s,1H),8.77(s,1H),8.67(s,1H),8.32(d,J=8.6Hz,1H), 8.24(dd, J = 8.0, 2.0 Hz, 1H), 8.08 (s, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.90 (d, J = 8.6 Hz, 1H), 7.68 (d, J = 3.5 Hz, 1H), 7.50 (d, J = 3.5 Hz, 1H), 7.45 (t, J = 7.9 Hz, 1H), 7.41 (td, J = 8.7 Hz, 2.7 Hz, 1H), 7.29-7.28 (m, 2H) ,4.21(s,1H),4.14(brs,2H),3.41(brs,2H),3.29-3.22(m,4H),1.22(t,J=6.7Hz,6H); 13 C NMR(151MHz, DMSO-d 6 )δ(ppm): 164.0, 159.0, 157.8, 157.4, 157.3, 154.1(d, 1 J C-F =270Hz),150.8,149.9,149.1,140.6,1...

Embodiment 3

[0046] Synthetic compound C

[0047]

[0048] In this example, the equimolar (Z)-1-(diethylaminoethyl)-3-hydrazone-5-chloroindolin-2-one is used to replace (Z)-1-(二) in Example 1. Ethylaminoethyl)-3-hydrazone indolin-2-one, other steps are the same as in Example 1, to obtain 0.1409g of compound C as a red solid, the yield is 76.2%, mp278.7-281.0℃, structural characterization data For: HRMS(C 35 H 30 ClN 7 O 2 )m / z[M+H] + : 616.2218 (calculated value: 616.2228); 1 H NMR(600MHz, DMSO-d 6 )δ(ppm): 10.13(s,1H),9.09(s,1H),8.80(s,1H),8.67(s,1H),8.55(brs,1H),8.37(d,J=8.6Hz, 1H), 8.03 (s, 1H), 7.91 (d, J = 8.2 Hz, 2H), 7.65 (d, J = 3.1 Hz, 1H), 7.61 (d, J = 7.9 Hz, 1H), 7.50 (d, J = 3.1Hz, 1H), 7.45 (t, J = 8.0Hz, 1H), 7.31-7.27 (m, 2H), 4.23 (s, 1H), 4.14 (brs, 2H), 3.40 (brs, 2H), 3.26(brs,4H),1.21-1.20(m,6H); 13 C NMR(151MHz, DMSO-d 6 )δ(ppm): 163.7, 157.8, 157.2, 155.0, 153.2, 150.8, 148.9, 142.9, 139.1, 132.6, 129.0, 128.9, 128.6, 127.1, 126.6, 125.4, 124.3, 123.1, 121.8, 119.6, 1...

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Abstract

The invention discloses an isatin derivative synthesized by N-substituted isatin hybrid quinazoline compound and an application of the isatin derivative in preparation of anti-tumor drugs, wherein thestructure formula of the derivative is described in the description, X represents hydrogen, fluorine, chlorine, bromine or iodine, Ar represents 3-ethynyl phenyl, 3-chlorine-4-fluorophenyl, 3-chloro-4-(3-fluorobenzyloxy) phenyl group or a 4-(E)-propenyl phenyl group. The synthetic method of the isatin derivative is simple and has an obvious inhibiting effect on is suitable for human skin squamouscarcinoma cells A431, human colon cancer cells SW480, human non-small cell lung cancer cells A549 and human lung cancer cells NCI-H1975, and can be used for preparing anti-tumor drugs.

Description

Technical field [0001] The invention belongs to the technical field of the synthesis of anti-tumor drugs, and specifically relates to a new type of isatin synthesized by N-substituted isatin hydrazone hybrid 4-arylamino-6-(5-formylfuran-2-yl)quinazoline Derivatives, and their use in the preparation of anti-tumor drugs. Background technique [0002] Cancer, also known as malignant tumor, is one of the diseases that seriously endanger human health. The traditional treatment methods for malignant tumors include radiotherapy, surgical treatment, and chemotherapy, but they all have certain limitations. Most anti-cancer drugs are cytotoxic drugs. While these drugs kill cancer cells, they also have great toxic side effects on normal human tissue cells. Therefore, the development and synthesis of highly selective anticancer drugs has become a hot spot in the research field. In recent years, people have begun to pay attention to the research of drugs targeting key genes, regulatory mol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14A61K31/517A61P35/00
CPCC07D405/14
Inventor 王伟吕梦娇李宝林张娅玲张颖李夏冰
Owner SHAANXI NORMAL UNIV
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