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Chromene [2,3-b] quinoline derivative as well as preparation method and application thereof

A technology of derivatives and chromenes, applied in the field of organic synthesis, can solve the problems of cytotoxic activity and other problems, and achieve the effect of simple and convenient synthetic process route, good in vitro proliferation inhibition effect, and mild conditions

Active Publication Date: 2017-07-21
JIANGSU UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Recently, it has been reported in the literature that derivatives such as chromenoquinolines with a spiro ring structure have good antitumor activity, and the results show that this type of compound has cytotoxic activity against breast cancer and cervical cancer.

Method used

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  • Chromene [2,3-b] quinoline derivative as well as preparation method and application thereof
  • Chromene [2,3-b] quinoline derivative as well as preparation method and application thereof
  • Chromene [2,3-b] quinoline derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Add 2-chloroquinoline-3-carbaldehyde (0.2mmol), malononitrile (0.2mmol) and 5,5-dimethyl-1,3-cyclohexanedione (0.2mmol) into a 5mL microwave reaction tube, Then add L-proline (0.1mmol) and ethanol 2mL, seal the reaction tube, stir for 10 seconds in advance, and react the mixture at 100°C for 30 minutes under microwave radiation. After the reaction, cool the reaction system to room temperature and wait for precipitation Suction filtration after the solid, and then recrystallization with a mixed solvent of DMF and water to obtain 2-(3,3-dimethyl-1-oxo-2,3,4,12-tetrahydro-1H-chromene and [2,3-b]quinolin-12-yl)malononitrile (Ia): Yield 71%; m.p.: 248-250°C; IR (KBr, ν, cm -1 ):3047,2920,2254,1622,1598,1448,1399,1215,1091,1055,1027,999,752,689; 1 H NMR (400MHz, DMSO-d 6 )(δ,ppm):8.71(s,1H,ArH),8.07(d,J=7.6Hz,1H,ArH),7.94(d,J=8.4Hz,1H,ArH),7.88-7.84(m, 1H, ArH), 7.67-7.63(m, 1H, ArH), 5.23(d, J=4.0Hz, 1H, CH), 5.00(d, J=4.0Hz, 1H, CH), 2.81(d, J= 18.0Hz,1H,CH),2.68(d,J=18...

Embodiment 2

[0021] According to the method for embodiment 1, 2-chloroquinoline-3-formaldehyde is changed into 6-methoxyl group-2-chloroquinoline-3-formaldehyde, with L-proline as catalyst, reacted under microwave radiation for 30 minutes, Recrystallization with a mixed solvent of DMF and water gave the target product 2-(9-methoxy-3,3-dimethyl-1-oxo-2,3,4,12-tetrahydro-1H-chromeno [2,3-b]quinolin-12-yl)malononitrile (Ib): 74% yield; m.p.: 268-270°C; IR (KBr, ν, cm -1 ):2896,2254,1635,1613,1466,1356,1238,1216,1142,1112,1029,834; 1 H NMR (400MHz, DMSO-d 6 )(δ,ppm):8.57(s,1H,ArH),7.84(d,J=9.2Hz,1H,ArH),7.51-7.48(m,1H,ArH),7.45(d,J=2.4Hz, 1H, ArH), 5.20(d, J=4.0Hz, 1H, CH), 4.97(d, J=3.6Hz, 1H, CH), 3.93(s, 3H, CH 3 O), 2.79(d, J=17.6Hz, 1H, CH), 2.65(d, J=17.2Hz, 1H, CH), 2.45(d, J=16.4Hz, 1H, CH), 2.33(d, J =16.4Hz,1H,CH),1.15(s,3H,CH 3 ),1.13(s,3H,CH 3 ).

Embodiment 3

[0023] According to the method for Example 1, 2-chloroquinoline-3-formaldehyde is replaced with 6-tert-butyl-2-chloroquinoline-3-formaldehyde, and L-proline is used as a catalyst to react under microwave radiation for 30 minutes, Recrystallization with a mixed solvent of DMF and water gave the target product 2-(9-tert-butyl-3,3-dimethyl-1-oxo-2,3,4,12-tetrahydro-1H-chromene [2,3-b]quinolin-12-yl)malononitrile (Ic): 75% yield; m.p.: 228-230°C; IR (KBr, ν, cm -1 ):2960,2937,2254,1642,1611,1439,1394,1346,1265,1236,1212,1174,1145,1118,1024,997,831; 1 HNMR (400MHz, DMSO-d 6 )(δ,ppm):8.68(s,1H,ArH),8.01-7.89(m,3H,ArH),5.25(d,J=3.6Hz,1H,CH),4.99(d,J=3.6Hz, 1H, CH), 2.81(d, J=18.0Hz, 1H, CH), 2.52(d, J=18.8Hz, 2H, CH 2 ), 2.36(d, J=16.0Hz, 1H, CH), 1.41(s, 9H, (CH 3 ) 3 C).

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Abstract

The invention discloses a chromene [2,3-b] quinoline derivative. The structure formula of the derivative is as shown in the specification, in the formula, R1 is any one of H, CH3O, C1 or (CH3)3C; R2 is H or CH3; R3 is H, CH3 or Ph. The derivative is synthesized at one step from 2-chloroquinoline-3-formaldehyde or a derivative thereof, malononitrile and 1,3-cyclohexanedione or derivatives thereof as raw materials. The derivative is simple and rapid in synthesis process route and gentle in condition, and the total yield is up to 61% or greater. Pharmacology experiment of the compound disclosed by the invention shows that the derivative has a relatively good in-vitro inhibition multiplication function upon a human liver cancer cell system HepG2, has a function of inhibiting tumor cell growth and can be applied to preparation of anti-tumor medicines.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a preparation method of chromeno[2,3-b]quinoline derivatives and their application in antitumor drugs Background technique [0002] Chromene, also known as benzopyran, its skeleton widely exists in natural products, for example, vitamin E, flavonoids, isoflavones, etc. all contain chromene skeleton. Chromene derivatives have a wide range of biological and pharmacological activities. There have been reports of anti-allergic and anti-cancer activities. [0003] Quinoline, also known as benzopyridine or aziridine, is a very important class of nitrogen-containing heterocyclic compounds, especially in the pharmaceutical industry and has a wide range of applications. Moreover, they are also the mother nucleus of the structure of many natural products and bioactive drugs, such as: chloroquine, camelline, camptothecin. After continuous research by pharmacologists, a large numb...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/052A61P35/00
CPCC07D491/052
Inventor 林伟蔡琦胡秀秀王雅珍王赟
Owner JIANGSU UNIV OF TECH
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