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

A 3-b, derivative 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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Problems solved by technology

However, some of these preparation methods 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 preparation method and its application in antitumor
  • A pyrano[2,3-b]quinoline derivative, its preparation method and its application in antitumor
  • A pyrano[2,3-b]quinoline derivative, its preparation method and its application in antitumor

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preparation example Construction

[0025] In the preparation method of the present invention, the molar ratio of the compound of formula II, malononitrile, 4-hydroxyquinolin-2-one and catalyst is 1:1:1:0.1-0.6.

[0026] In the preparation method of the present invention, the solvent used is one of ethanol, toluene, tetrahydrofuran, ethylene glycol, N,N-dimethylformamide, water or acetonitrile.

[0027] In the preparation method of the present invention, the catalyst used can be a base, an acid, or a small organic molecule catalyst; the base is one of sodium hydroxide, sodium carbonate, cesium carbonate or hexahydropyridine, The acid is one of p-toluenesulfonic acid or acetic acid, and the small organic molecule catalyst is L-proline.

[0028] More specifically, the reaction temperature of the preparation method of the present invention is 80-110° C., and the reaction time is 20-50 minutes.

[0029] Through the screening of multiple reaction conditions, and considering the effect of the reaction and the princip...

Embodiment 1

[0032] Add 2-chloroquinoline-3-carbaldehyde (0.2mmol), malononitrile (0.2mmol) and 4-hydroxyquinolin-2-one (0.2mmol) into a 5mL microwave reaction tube, then add L-proline (0.1mmol) and ethanol 2mL, the reaction tube was sealed, stirred for 10 seconds in advance, and the mixture was reacted at 100°C for 30 minutes under microwave radiation. After the reaction was completed, the reaction system was cooled to room temperature, and the solid was precipitated. Recrystallization with a mixed solvent of DMF and water gave 2-(6-oxo-6,7-dihydro-5H-pyrano[2,3-b:5,6-c']bisquinoline-7 -yl) malononitrile (Ia): Yield 70%; m.p.:>300℃; IR(KBr,ν,cm- 1 ):2964,2185,1654,1613,1578,1421,1397,1344,1326,1255,1180,1151,1110,795; 1 H NMR (400MHz, DMSO-d 6 )(δ,ppm):12.23(s,1H,NH),8.82(s,1H,ArH),8.14-8.11(m,2H,ArH),8.03(d,J=8.4Hz,1H,ArH), 7.90(t, J=8.4Hz, 1H, ArH), 7.72-7.65(m, 2H, ArH), 7.46(d, J=8.0Hz, 1H, ArH), 7.40(t, J=7.6Hz, 1H, ArH), 5.41(d, J=3.6Hz, 1H, CH), 5.29(d, J=3.6Hz, 1H, CH). 13 ...

Embodiment 2

[0034] 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 Hydrogen-5H-pyrano[2,3-b:5,6-c']bisquinolin-7-yl)malononitrile (Ib): Yield 68%; m.p.:>300℃; IR(KBr,ν,cm- 1 ):2963,2185,1653,1609,1576,1504,1435,1328,1262,1241,1185,1094,1029,928,897,829,750; 1 H NMR (400MHz, DMSO-d 6 )(δ,ppm):12.26(s,1H,NH),8.80(s,1H,ArH),8.15(d,J=7.6Hz,1H,ArH),8.07-7.98(m,3H,ArH), 7.76-7.72(m,1H,ArH),7.50-7.41(m,2H,ArH),5.42(d,J=3.2Hz,1H,CH),5.30(d,J=3.2Hz,1H,CH), 1.45(s,9H,(CH 3 ) 3 C). 13 C NMR (100MHz, DMSO-d 6 )(δ,ppm):161.1,156.3,154.7,149.6,144.6,141.0,138.9,132.8,131.1,127.6,126.9,123.3,123.2,122.8,116.3,113.6,113.0,112.7,10...

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Abstract

The present invention relates to a kind of pyrano[2,3-b]quinoline derivatives and its preparation method and the application in antitumor aspect, and this preparation method utilizes multi-component reaction, with formula II compound, malononitrile and 4 -Hydroxyquinoline-2-ketone is a raw material, and through a three-component reaction under solvent, catalyst catalysis and microwave radiation, one-step synthesis obtains the target compound, i.e. pyrano[2,3-b]quinoline derivatives (formula I). The advantage of the present invention is that: the preparation method 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 particularly relates to pyrano[2,3-b]quinoline derivatives, a preparation method thereof and an antitumor 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): C07D491/147A61P35/00
CPCC07D491/147
Inventor 朱春林吴玉祥严宾
Owner JINGHUA PHARMA GRP NANTONG
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