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Isatin derivative synthesized by isatin hybrid quinazoline compound and application thereof in preparing antineoplastic drugs

A technology of hybrid quinazoline and anti-tumor drug, which is applied in the field of preparing anti-tumor drugs, can solve problems such as difficult post-treatment treatment of tumors, and achieve the effect of simple synthesis method

Active Publication Date: 2017-05-10
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 obvious drug resistance, which will bring difficulties to the later treatment of tumors

Method used

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  • Isatin derivative synthesized by isatin hybrid quinazoline compound and application thereof in preparing antineoplastic drugs
  • Isatin derivative synthesized by isatin hybrid quinazoline compound and application thereof in preparing antineoplastic drugs
  • Isatin derivative synthesized by isatin hybrid quinazoline compound and application thereof in preparing antineoplastic drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Synthetic Compound A

[0045]

[0046] 0.17g (0.5mmol) 4-(3-ethynylanilino)-6-(5-formyl furan-2-yl) quinazoline, 0.08g (0.5mmol) (Z)-3-hydrazone indole Phenolin-2-one, 0.5mL acetic acid, 10mL ethanol and 2mL N,N-dimethylformamide were added to the reaction flask, refluxed at 80°C for 6 hours, cooled to room temperature after the reaction, suction filtered, and washed with ethanol Rinse the filter cake, and recrystallize the filter cake in dimethyl sulfoxide to obtain 0.18 g of red solid, Compound A, with a yield of 73.5%, m.p.>280°C, and the structural characterization data are: HRMS (C 29 h18 N 6 o 2 )m / z[M+H] + :483.1581 (calculated value 483.1569); 1 H NMR (300MHz, DMSO-d 6 )δ(ppm):10.85(s,1H),10.15(s,1H),9.02(s,1H),8.68(s,2H),8.35(d,J=8.0Hz,2H),8.08(s, 1H), 8.02(d, J=8.3Hz, 1H), 7.92(d, J=8.8Hz, 1H), 7.59(d, J=3.4Hz, 1H), 7.47(d, J=4.6Hz, 1H) ,7.42(d,J=4.6Hz,1H),7.38(d,J=7.8Hz,1H),7.28(d,J=7.5Hz,1H),7.06(t,J=7.4Hz,1H),6.91 (d,J=7.9Hz,1H),4.25(s,1H); 13 C...

Embodiment 2

[0048] Synthetic Compound B

[0049]

[0050] In Example 1, the (Z)-3-hydrazone indoline-2-one used is replaced with equimolar (Z)-3-hydrazone-5-fluoroindoline-2-one, other steps and implementation Example 1 is the same, obtains red solid and is compound B 0.18g, and its yield is 72.6%, m.p.>280 ℃, and structural characterization data is: HRMS (C 29 h 17 FN 6 o 2 )m / z[M+H] + :501.1491 (calculated value 501.1475); 1 H NMR (400MHz, DMSO-d 6 )δ(ppm):10.83(s,1H),10.05(s,1H),9.00(s,1H),8.67(s,1H),8.63(s,1H),8.26(d,J=8.8Hz, 1H), 8.07(d, J=9.2Hz, 2H), 7.95(d, J=8.3Hz, 1H), 7.85(d, J=8.6Hz, 1H), 7.58(d, J=3.3Hz, 1H) ,7.42(t,J=7.8Hz,2H),7.26(d,J=7.9Hz,1H),7.21(d,J=8.7Hz,1H),6.86(dd,J=8.4,4.1Hz,1H) ,4.20(s,1H); 13 C NMR (151MHz, DMSO-d 6 )δ (ppm): 164.8, 158.4, 157.7, 157.0, 155.9 (d, 1 J C-F =277.9Hz), 152.3, 151.6(d, 4 J C-F =2.5Hz), 150.0, 149.1, 141.1, 139.2, 129.0, 128.9, 128.8, 127.0, 126.7, 125.2, 122.9, 121.8, 120.0, 119.9, 119.2, 117.2 (d, 3 J C-F =9.2Hz), 11...

Embodiment 3

[0052] Synthetic Compound C

[0053]

[0054] In Example 1, the (Z)-3-hydrazone indoline-2-one used is replaced with equimolar (Z)-3-hydrazone-5-chloroindoline-2-one, other steps and implementation Example 1 is the same, obtains red solid and is compound C 0.20g, and its yield is 76.3%, m.p.>280 ℃, and structural characterization data is: HRMS (C 29 h 17 ClN 6 o 2 )m / z[M+H] + :517.1182 (calculated value: 517.1180); 1 HNMR (600MHz, DMSO-d 6 )δ(ppm):10.90(s,1H),9.96(s,1H),8.93(s,1H),8.64(s,1H),8.59(s,1H),8.33(s,1H),8.24( d,J=8.7Hz,1H),8.00(s,1H),7.90(d,J=8.0Hz,1H),7.78(d,J=8.6Hz,1H),7.50(s,1H),7.42( t, J=7.9Hz, 1H), 7.37(s, 2H), 7.26(d, J=7.4Hz, 1H), 6.84(d, J=8.2Hz, 1H), 4.20(s, 1H); 13 C NMR (151MHz, DMSO-d 6 )δ (ppm): 164.5, 157.8, 157.0, 155.6, 155.0, 152.4, 150.0, 149.1, 143.5, 143.4, 139.2, 132.9, 129.1, 128.9, 127.1, 127.0, 126.7, 126.1, 126.4, 1218.2 119.3, 118.0, 115.5, 112.2, 110.5, 83.4, 80.6; IRν max (KBr)cm -1 : 3555, 3416, 3235, 2062, 1719, 1638, 161...

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Abstract

The invention discloses an isatin derivative synthesized by an isatin hybrid quinazoline compound and application thereof in preparing antineoplastic drugs. The structural formula of the derivative is shown in the description, wherein X represents hydrogen, fluorine, chlorine, bromine or iodine, Ar represents 3-acetenyl phenyl, 4-(E)-allyl phenyl, 3-Chloro-4-(3-fluorobenzyloxy)-phenyl or 3-chloro-4-fluorophenyl. The synthesis method of the isatin derivative is simple, and the isatin derivative synthesized by an isatin hybrid quinazoline compound has obvious inhibition effect on the proliferation of human skin squamous cancer cells A431, human lung cancer cells NCI-H1975, human colon cancer cells SW480 and human non-small cell lung cancer cells A549 and can be applied in preparing the antineoplastic drugs.

Description

technical field [0001] The invention belongs to the technical field of synthesis of antineoplastic drugs, in particular to a novel isatin derivative synthesized from a novel isatin hydrazone hybrid 4-arylamino-6-(5-formylfuran-2-yl)quinazoline, As well as their preparation methods and their use in the preparation of antineoplastic drugs. Background technique [0002] Cancer is one of the threats to human health. Traditional anticancer drugs are mostly cytotoxic drugs. While killing cancer cells, these drugs also have great toxic and side effects on normal human tissue cells. In order to improve the anticancer effect of drugs The selectivity of cellular action, people have begun to pay attention to the research of drugs targeting key genes, regulatory molecules and specific cell receptors. [0003] Studies have shown that when tyrosine kinases are overactivated, cell growth regulation is out of control, cell death is blocked, and cells are always in a state of proliferation,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14A61K31/517A61P35/00
Inventor 王伟张颖张娅玲李宝林吕梦娇陈丽李夏冰
Owner SHAANXI NORMAL UNIV
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