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A pyrano[2,3-b]quinoline derivative, its synthesis process and its application in antitumor

A synthetic process, 3-b technology, applied in the direction of antineoplastic drugs, drug combinations, organic chemistry, etc., can solve the problem that the synthetic raw materials are not easy to obtain, and achieve a good effect of inhibiting proliferation in vitro

Active Publication Date: 2021-11-23
JINGHUA PHARMA GRP NANTONG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, some of these synthetic processes need to use noble metals as catalysts, and some synthetic raw materials are not easy to obtain

Method used

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  • A pyrano[2,3-b]quinoline derivative, its synthesis process and its application in antitumor
  • A pyrano[2,3-b]quinoline derivative, its synthesis process and its application in antitumor
  • A pyrano[2,3-b]quinoline derivative, its synthesis process and its application in antitumor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add 2-chloroquinoline-3-carbaldehyde (0.2mmol), malononitrile (0.2mmol) and 4-hydroxycoumarin (0.2mmol) into a 5mL microwave reaction tube, then add L-proline (0.1mmol ) and 2 mL of ethanol, seal the reaction tube, stir for 10 seconds in advance, and react the mixture at 100°C for 30 minutes under microwave radiation. A mixed solvent of water was recrystallized to obtain 2-(6-oxo-6,7-dihydrochromeno[3',4':5,6]pyrano[2,3-b]quinoline-7 -yl) malononitrile (Ia): Yield 71%; m.p.:274-276°C; IR(KBr,ν,cm -1 ):2917,2250,1701,1638,1607,1493,1404,1332,1244,1204,1169,1151,1050,1025,987,769,754; 1 H NMR (400MHz, DMSO-d 6 )(δ,ppm):8.84(s,1H,ArH),8.15(d,J=8.0Hz,2H,ArH),8.04(d,J=8.4Hz,1H,ArH),7.94-7.90(m, 1H, ArH), 7.86-7.82(m, 1H, ArH), 7.70(t, J=7.6Hz, 1H, ArH), 7.61(d, J=8.4Hz, 1H, ArH), 7.57(t, J= 8.0Hz, 1H, ArH), 5.38(d, J=4.0Hz, 1H, CH), 5.34(d, J=3.6Hz, 1H, CH). 13 C NMR (100MHz, DMSO-d 6 )(δ,ppm):162.3,160.0,158.5,153.7,152.6,145.6,140.8,134.0,131.9,128.3,127.6,127.0,12...

Embodiment 2

[0035] 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, After the reaction, the reaction system was cooled to room temperature, and after the solid was precipitated, suction filtration was performed, and the target product 2-(10-methoxy-6-oxo-6,7-di Hydrochromeno[3',4':5,6]pyrano[2,3-b]quinolin-7-yl)malononitrile (Ib): Yield 75%; m.p.:258-260°C; IR(KBr,ν,cm -1 ):2903,2254,1686,1637,1609,1497,1455,1353,1236,1172,1113,1025,1005,993,794,747; 1 H NMR (400MHz, DMSO-d 6 )(δ,ppm):8.69(s,1H,ArH),8.14-8.11(m,1H,ArH),7.94(d,J=9.2Hz,1H,ArH),7.85-7.81(m,1H,ArH ),7.61-7.53(m,4H,ArH),5.35(d,J=3.6Hz,1H,CH),5.31(d,J=3.6Hz,1H,CH),3.94(s,3H,CH 3 O). 13 C NMR (75MHz, DMSO-d 6 )(δ,ppm):160.5,159.0,158.1,153.1,152.6,141.7,139.6,134.4,129.5,128.6,125.7,124.9,123.4,117.4,113.7,113.6,113.2,112.9,106.4,67.7 , 30.8. HRMS Calcd...

Embodiment 3

[0037] 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, After the reaction, the reaction system was cooled to room temperature, and after the solid was precipitated, suction filtration was performed, and the target product 2-(10-tert-butyl-6-oxo-6,7-di Hydrochromeno[3',4':5,6]pyrano[2,3-b]quinolin-7-yl)malononitrile (Ic): Yield 73%; m.p.:284-286°C; IR(KBr,ν,cm -1 ):2963,2255,1702,1640,1610,1497,1460,1438,1396,1380,1366,1271,1183,1169,1150,1126,1098,988,969,915,831; 1 H NMR (400MHz, DMSO-d 6 )(δ,ppm):8.82(s,1H,ArH),8.17(d,J=7.6Hz,1H,ArH),8.09-8.00(m,3H,ArH),7.86(t,J=8.0Hz, 1H, ArH), 7.64-7.58(m, 2H, ArH), 5.38(d, J=3.6Hz, 1H, CH), 5.34(d, J=3.6Hz, 1H, CH), 1.45(s, 9H, (CH 3 ) 3 C). 13 C NMR (75MHz, DMSO-d 6 )(δ,ppm):160.5,158.9,153.9,153.1,150.0,144.5,141.1,134.5,131.4,127.7,127.1,125.7,123.4,117.4...

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Abstract

The present invention relates to a pyrano[2,3-b]quinoline derivative and its synthesis process and application in anti-tumor. The synthesis process utilizes multi-component reaction to obtain chemical formula II, malononitrile and 4- Hydroxycoumarin is used as a raw material, and the target compound, namely pyrano[2,3‑b]quinoline derivative (Formula I), is synthesized in one step through a three-component reaction under solvent, catalyst catalysis and microwave irradiation. The advantage of the present invention is that: the synthesis process of the present invention utilizes multi-component reaction to synthesize a pyrano[2,3-b]quinoline derivative from three raw materials through the method of "one-pot cooking", which is a kind of Quite stable compounds, these compounds have good in vitro anti-proliferation effect on human liver tumor cell line HepG2.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to pyrano[2,3-b]quinoline derivatives, their synthesis process and their anti-tumor application. Background technique [0002] Pyran is an important class of heterocyclic compounds, and its derivatives have a wide range of biological and pharmacological activities, such as antiallergic effects (Witte, E.C.; Neubert, P.; Roesoh, A.DE 3427985, 1986), hypoglycemic effects (Jiang Hong, Wang Lijun, Zhao Zhixue, Journal of Beihua University (Natural Science Edition), 2001, 2, 489), anticancer activity (Hyama, T.; Saimoto, H.JP62181271, 1987), can be used to treat allergic tracheitis ( Chand, N.; Diamantis, W.; Sofia, R.D.Br.J.Pharmacol., 1986, 87, 443), anti-dysplasia (Brooks, G.T.; Ottridge, A.P.; Maee, D.W.Pestic. SCi., 1988, 22, 41 ) and treatment of diabetes (Suarez, M.; Ochoa, E.; Verdecia, Y.; Martin, M.; Quinteiro, C.; Seoane, J.; Soto, J.L.; Novoa, N.; Blato...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/153A61P35/00
CPCC07D491/153
Inventor 吴玉祥严宾朱春林
Owner JINGHUA PHARMA GRP NANTONG
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