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3-(2-aryl-1H-indol-3-yl)-4-hydroxycoumarin derivative and synthetic method thereof

A technology of hydroxycoumarin and its synthesis method, which is applied in the field of new compound 3--4-hydroxycoumarin derivatives and its synthesis, and can solve the problems of low bioavailability, limited clinical application, and limited natural existence , to achieve the effect of simple conditions, high atom economy and short reaction time

Active Publication Date: 2016-10-12
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Natural coumarin has good anti-tumor activity, but also because of its small amount of natural existence and low bioavailability, its clinical application is limited

Method used

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  • 3-(2-aryl-1H-indol-3-yl)-4-hydroxycoumarin derivative and synthetic method thereof
  • 3-(2-aryl-1H-indol-3-yl)-4-hydroxycoumarin derivative and synthetic method thereof
  • 3-(2-aryl-1H-indol-3-yl)-4-hydroxycoumarin derivative and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Add 4-hydroxycoumarin (1mmol), phenylglyoxal (1mmol), p-methylaniline (1mmol) into the microwave reaction tube, and then add 4mL EtOH / H 2 O (volume ratio is 1:1), shake slightly to mix the substrate evenly, add dropwise (0.2mmol) trifluoroacetic acid, react in a microwave reactor at 90°C for 40min, monitor the reaction progress with TLC, after the reaction is completed, , cooling, the reaction mixture was obtained by column chromatography as 3-(5-methyl-2-phenyl-1H-indol-3-yl)-4-hydroxycoumarin (compound IVa), and the yield was 49%; melting point is 244-245°C; 1 H NMR (400MHz, DMSO-d 6 )δ (ppm): 11.49 (s, 1H, OH), 11.00 (s, 1H, NH), 7.91 (d, J = 7.6Hz, 1H, ArH), 7.67 (t, J = 8.8Hz, 1H, ArH ), 7.60(d, J=8.0Hz, 2H, ArH), 7.44(d, J=8.0Hz, 1H, ArH), 7.40-7.34(m, 4H, ArH), 7.26(t, J=7.2Hz, 1H, ArH), 6.99(t, J=6.0Hz, 2H, ArH), 2.34(s, 3H, CH 3 ).

Embodiment 2

[0045] According to the method of Example 1, p-methylaniline was replaced by p-tert-butylaniline, trifluoroacetic acid was used as a catalyst, microwave reaction was carried out at 90°C for 40 minutes, and the target product was obtained by column chromatography, which was 3-(5-tert-butyl -2-phenyl-1H-indol-3-yl)-4-hydroxycoumarin (compound IVb), yield 75%; melting point 174~175°C; 1 H NMR (400MHz, DMSO-d 6 )δ (ppm): 11.51 (s, 1H, OH), 10.96 (s, 1H, NH), 7.93 (d, J = 8.0Hz, 1H, ArH), 7.67 (t, J = 8.8Hz, 1H, ArH ), 7.67(t, J=7.2Hz, 1H, ArH), 7.61(d, J=7.6Hz, 2H, ArH), 7.44(t, J=8.4Hz, 2H, ArH), 7.38(t, J= 8.0Hz,3H,ArH),7.29-7.25(m,2H,ArH),7.19(s,1H,ArH),1.30(s,9H,(CH 3 ) 3 C).

Embodiment 3

[0047] According to the method of Example 1, p-methylaniline was replaced by m-chloroaniline, and trifluoroacetic acid was used as a catalyst, and reacted at 90° C. for 40 minutes under microwave radiation, and the target product was obtained by column chromatography, which was 3-(6-chloro- 2-Phenyl-1H-indol-3-yl)-4-hydroxycoumarin (compound IVc), yield 31%; melting point 253-254°C; 1 H NMR (400MHz, DMSO-d 6 )δ (ppm): 11.82 (s, 1H, OH), 11.12 (s, 1H, NH), 7.93 (d, J = 8.0Hz, 1H, ArH), 7.69-7.62 (m, 3H, ArH), 7.50 (s, 1H, ArH), 7.46-7.36 (m, 4H, ArH), 7.32-7.26 (m, 2H, ArH), 7.03 (d, J=8.0Hz, 1H, ArH).

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Abstract

The invention discloses a 3-(2-aryl-1H-indol-3-yl)-4-hydroxycoumarin derivative and a synthetic method thereof. The synthetic method utilizes multiple components for reaction, and takes 4-hydroxycoumarin, substituted phenylglyoxal and substituted aniline as raw materials, and through reaction of the three components under the action of a catalyst and microwave radiation, the 3-indolyl substituted 4-hydroxycoumarin derivative is obtained through one-step synthesis. The 3-(2-aryl-1H-indol-3-yl)-4-hydroxycoumarin derivative is a brand-new compound of which the molecules contain benzazole and coumarin skeleton and has good bioactivity and a potential application value. Compared with the prior art, the synthetic method has the advantages of short reaction time, simple condition, high yield, high atom economy, convergence, easiness in operation and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a novel compound 3-(2-aryl-1H-indol-3-yl)-4-hydroxycoumarin derivative and a synthesis method thereof. Background technique [0002] Coumarin is a kind of organic oxygen-containing heterocyclic compound with δ-pyranolactone ring structure. Coumarins can be divided into simple coumarins, furanocoumarins, pyranocoumarins and substituted α-pyrone coumarins according to the substituents on the ring and the positions of the substituents. In the metabolites of higher plants and microorganisms such as Asteraceae, Compositae, Orchidaceae, Solanaceae, and Daphneaceae. These compounds have good pharmaceutical physiological activities, such as: anti-tumor, anti-infection, anti-oxidation, anti-allergic, anti-thrombotic, anti-viral, antibacterial and hepatoprotective effects (Yang Shilin, Rena Kasimu, Natural Medicinal Chemistry, Science Press, 2010). Among them, umbelliferone ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04
CPCC07D405/04
Inventor 史达清黄志斌荀展
Owner SUZHOU UNIV
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