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Synthetic method of trans-tetrahydroisoquinolone-4-carboxylic acid derivatives and medical application

A tetrahydropyrrole-based, pharmaceutical technology, used in drug combinations, anti-tumor drugs, organic chemistry, etc., can solve problems such as low toxicity and high efficiency, and no very satisfactory treatment methods.

Inactive Publication Date: 2015-07-01
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cancer has become a major disease that seriously endangers human health and life, and there is still no satisfactory treatment method so far, so it is imminent to develop anti-tumor drugs with low toxicity and high efficiency

Method used

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  • Synthetic method of trans-tetrahydroisoquinolone-4-carboxylic acid derivatives and medical application
  • Synthetic method of trans-tetrahydroisoquinolone-4-carboxylic acid derivatives and medical application
  • Synthetic method of trans-tetrahydroisoquinolone-4-carboxylic acid derivatives and medical application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Synthesis of Perphthalic Anhydride (II-1)

[0040] Dissolve 2.0g (11.1mmol) of perphthalic acid in 20ml of dry toluene, add 1.3ml (13.3mmol) of acetic anhydride dropwise, heat to reflux for 1 hour under the protection of nitrogen, and determine the end point by TLC. After the reaction solution is cooled, it is concentrated under reduced pressure to remove the solvent. 1.8 g of a light yellow solid was obtained with a yield of 99%. MS (ESI, m / z): 163 [M+H] + .

Embodiment 2

[0042] Synthesis of 4-methoxyperphthalic anhydride (II-2)

[0043] Dissolve 2.0g (9.5mmol) of 4-methoxyperphthalic acid in 20ml of dry toluene, add dropwise 1.1ml (11.4mmol) of acetic anhydride, heat and reflux for 1 hour under the protection of nitrogen, and determine the end point by TLC. Concentrate under reduced pressure to remove the solvent to obtain 1.7 g of light yellow solid with a yield of 99%. MS (ESI, m / z): 193 [M+H] + .

Embodiment 3

[0045] Synthesis of cis-N-methyl-1-oxo-3-phenyl-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid (IV-1)

[0046] Dissolve 5.0g (30.9mmol) of perphthalic anhydride II-1 in 60ml of acetonitrile, add 3.7g (30.9mmol) N-benzylidenemethylamine III-1 and 7.4g (15.5mmol) KA1(SO 4 ) 2 12H 2 O, react at room temperature for 8 hours, determine the end point by TLC, evaporate most of the solvent from the reaction solution under reduced pressure, add 100ml of water to the residue and stir for 10min, filter with suction, and wash the filter cake with methanol (25ml) and water (25ml) successively , 7.1 g of a white solid was obtained after drying, and the yield was 82%. 1 H-NMR (300MHz, DMSO-d6): δ12.24-12.25(s, 1H, 4-COOH), 6.54~7.42(m, 9H, Ar-H), 5.01~5.03(d, J=6.24Hz, 1H, 3-CH), 4.62~4.60 (d, J=6.24Hz, 1H, 4-CH), 2.90 (s, 3H, NCH 3 ); MS (ESI, m / z): 282 [M+H] + .

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Abstract

The invention relates to the field of medicinal chemistry and particularly relates to trans-tetrahydroisoquinolone-4-carboxylic acid derivatives with a structure shown in a formula I and medical application, particular application for preparing an inhibitor medicine of angiogenesis, as well as a preparation method of selectively synthesizing a trans-structural compound I which takes 1-ethyl-(3-dimethyl amino propyl) carbonyl diimine hydrochloride (EDCI) as a condensating agent, 1-hydroxyl benzotriazole (HOBT) as a catalyst and cis-structural IV and V as reactants. The formula is shown in the description.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a selective synthesis method of a trans-tetrahydroisoquinolinone-4-carboxylic acid derivative and its medical application, especially the application for preparing an angiogenesis inhibitor drug. Background technique [0002] Tumors are diseases characterized by the uncontrolled proliferation and spread of abnormal cells. The 2014 "Global Cancer Facts and Figures" report by the American Cancer Society shows that in 2012, there were 14 million new cancer cases and 8.2 million deaths worldwide, of which 3.07 million new cancer patients were added in China and about 2.2 million people died. Accounting for 21.9% and 26.8% of the global total, respectively. The report predicts that global cancer cases will show a rapid growth trend, from 14 million in 2012 to 19 million in 2025 and 24 million in 2035. Cancer has become a major disease that seriously endangers human health and life...

Claims

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Application Information

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IPC IPC(8): C07D217/26A61K31/4725A61K31/5377A61K31/496A61P35/00
CPCC07D217/26
Inventor 向华牛绍雄唐智超劳可静唐郑普王文宾陈明琪尤启冬
Owner CHINA PHARM UNIV
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