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Tryptanthrin derivative and medicinal use thereof

The technology of a derivative, tryptanthrin, is applied in the field of new tryptanthrin derivatives and their medicinal uses, which can solve the problems of difficult to obtain and isatoic anhydride derivatives, and achieve the goal of inhibiting tumor cells and simple synthesis method Effect

Inactive Publication Date: 2019-08-20
NORTHWEST UNIV(CN)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, isatoic anhydride derivatives are not easy to obtain, so tryptanthrin 1-4 derivatives are difficult to obtain

Method used

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  • Tryptanthrin derivative and medicinal use thereof
  • Tryptanthrin derivative and medicinal use thereof
  • Tryptanthrin derivative and medicinal use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Example 1. Synthesis of 2,7-dichloroindo[2,1-b]quinazoline-6,12-dione (1a):

[0072] Weigh 1.0g (0.0055mol) of 4-chloroisatin and 1.15g (0.0058mol) of 5-chloroisatic anhydride into a 100ml three-necked bottle equipped with a magnet, then add 40ml of chloroform to the three-necked bottle , 1.5ml of triethylamine, heating and refluxing in an oil bath at 80°C for 3h, after the reaction, stop heating, wait for cooling, and suction filter to obtain a yellow solid powder of the crude product, wash the product with 10ml of ethanol for 3 times, and obtain a yellow solid powder of the pure product , dried and weighed 1.12g, yield 64.4%.

[0073] 2,7-dichloroindole[2,1-b]quinazoline-6,12-dione (1a):

[0074] Yellow solid powder, yield 64.4%; m.p.291.2-293.4°C; 1 H NMR (400MHz, DMSO) δ8.47 (d, J = 8.1Hz, 1H), 8.29 (dd, J = 1.8, 1.0Hz, 1H), 8.02 (s, 1H), 7.92–7.84 (m, 1H) ,7.56(t,J=7.7Hz,1H),7.16(s,1H);IR(KBr)ν:3081,3030,1733,1686,1584,1549,1460,1418,915,796,726cm -1 ; EI-MS: c...

Embodiment 2

[0075] Example 2. Synthesis of 2,9-dichloroindo[2,1-b]quinazoline-6,12-dione (1b):

[0076] Weigh 0.3g (0.0017mol) of 6-chloroisatin and 0.36g (0.0018mol) of 5-chloroisatic anhydride and add them to a 100ml three-necked bottle with a magnet, then add 40ml of chloroform to the three-necked bottle , 1.5ml of triethylamine, heating and refluxing in an oil bath at 80°C for 3h, after the reaction, stop heating, wait for cooling, and suction filter to obtain a yellow solid powder of the crude product, wash the product with 10ml of ethanol for 3 times, and obtain a yellow solid powder of the pure product , dried, weighed 0.34g, and the yield was 63.0%.

[0077] 2,9-Dichloroindole[2,1-b]quinazoline-6,12-dione (1b):

[0078] Yellow solid powder, yield 63.0%; m.p.274.5-276.4°C; 1 H NMR (400MHz, DMSO) δ8.02(s, 1H), 7.94(s, 1H), 7.54(d, J=8.1Hz, 1H), 7.13(d, J=1.8Hz, 1H), 7.11(d ,J=1.8Hz,1H),6.95(d,J=1.7Hz,1H); IR(KBr)ν:3117,3060,1725,1678,1591,1553,1464,1428,847,775cm －1 ; EI-MS: cal...

Embodiment 3

[0079] Example 3. Synthesis of 2-chloro-9-bromoindo[2,1-b]quinazoline-6,12-dione (1c):

[0080] Weigh 0.70g (0.0031mol) of 6-bromoisatin and 0.66g (0.0033mol) of 5-chloroisatic anhydride and add them to a 100ml three-necked bottle equipped with a magnet, then add 40ml chloroform to the three-necked bottle , 1.5ml triethylamine, heating and refluxing in an oil bath at 80°C for 3h, after the reaction, stop heating, wait for cooling, and suction filter to obtain the crude product yellow solid powder, wash the product 3 times with 10ml ethanol to obtain the pure product yellow solid powder , dried, weighed 0.63g, and the yield was 56.3%.

[0081] 2-Chloro-9-bromoindole[2,1-b]quinazoline-6,12-dione (1c):

[0082] Yellow solid powder, yield 56.3%; m.p.283.4-285.1°C; 1 H NMR (400MHz, DMSO) δ8.66(d, J=1.6Hz, 1H), 8.32(d, J=2.1Hz, 1H), 8.05(s, 1H), 7.90(s, 1H), 7.88(s ,1H),7.78(d,J=1.6Hz,1H);IR(KBr)ν:3115,3068,1725,1678,1586,1552,1463,1421,911,843,755cm －1 ; EI-MS: calcd for C 15 ...

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Abstract

The invention discloses a tryptanthrin derivative and a medicinal use thereof. The chemical formula of the tryptanthrin derivative is shown in the description. The tryptanthrin derivative is preparedby a reaction of an isatoic anhydride derivative and an indoquinone derivative. The new compound tryptanthrin with a good inhibition effect on cancer cells is preliminarily screened by MTT experiments. The compound has a pharmacological effect in antitumor.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a new derivative of tryptanthrin and its medicinal use. Background technique [0002] Tryptanthrin (see formula Ⅰ for structure, chemical name is indole[2,1-b]quinazolin-6,12-dione (indolo[2,1-b]quinazolin-6,12-dione), exists In plants such as Strobilanthes cusia, Polygonum tinctorum Lour and Isatis Einetorial, it is also one of the main components of the traditional Chinese medicine Qingdai and Daqingye. Tryptanthrin and its derivatives have good anticancer , anti-inflammatory and antibacterial effects. [0003] [0004] Tryptanthrin is found in very small amounts in plants and is mainly obtained through synthesis. The research group studied the biosynthetic pathway of tryptanthrin, and developed a simple synthetic method: using indole quinone and its derivatives and isatoic anhydride and its derivatives as raw materials, under triethylamine alkaline conditions...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K31/519A61P35/00
CPCA61P35/00C07D487/04
Inventor 王翠玲白逍张晓斌刘建利
Owner NORTHWEST UNIV(CN)
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