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6,7-methylene-dioxy-1,2,3,4-tetrahydroisoquinoline derivative and preparation method and application thereof

A methylenedioxy, tetrahydroisoquinoline technology, applied in the direction of drug combination, pharmaceutical formula, medical preparations containing active ingredients, etc.

Inactive Publication Date: 2011-04-27
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005]The anti-tumor mechanism of narcotin and its derivatives is to act on microtubules, stabilize the conformation of microtubules, inhibit the dynamic instability of interfering microtubules, and thus prevent Cell mitosis, induction of apoptosis and anti-tumor activities, narcotin can cause cell apoptosis in G2 / M phase, some narcotin derivatives can cause cell apoptosis in S phase, these characteristics Noscapine and its derivatives can be developed as anti-tumor drugs, which has great potential, but its pharmacological activity is relatively limited

Method used

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  • 6,7-methylene-dioxy-1,2,3,4-tetrahydroisoquinoline derivative and preparation method and application thereof
  • 6,7-methylene-dioxy-1,2,3,4-tetrahydroisoquinoline derivative and preparation method and application thereof
  • 6,7-methylene-dioxy-1,2,3,4-tetrahydroisoquinoline derivative and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0104] Example 1: 5-[1-(2-chlorobenzyl)-3-indolyl]-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxa[4 ,5-g] Preparation of Isoquinoline (Compound 1)

[0105] 1) Preparation of 1,2-methylenedioxy-4-(2-nitro-vinyl)-benzene

[0106] Add 17.5g of piperonal (0.117mol) and 7.63g of ammonium acetate (0.096mol) into 100ml of glacial acetic acid, add dropwise 18.2ml of nitromethane, react at 105°C for 6h, and cool to room temperature. Suction filtration, washing the filter cake with a small amount of cold ethanol, and drying. 17.1 g was obtained, and the yield was 76%. Melting point: 161-163°C.

[0107] 2) Preparation of 2-(1,2-methylenedioxy-4-phenyl)-ethylamine hydrochloride

[0108] Under the condition of ice bath, 18g of lithium aluminum hydride (0.5mol) was dissolved in 800ml of dry tetrahydrofuran solution, and the reaction temperature was kept below 10°C. Slowly put 22.3g (0.1mol) of 1,2-methylenedioxy-4-(2-nitro-vinyl)-benzene into the reaction solution and stir at room temperature ...

Embodiment 2

[0119] Embodiment two: 5-[1-(3 -Chlorobenzyl ) - 3 -indolyl ]-6- methyl -5,6,7,8- Tetrahydro- [1,3] Dioxa [4,5-g] Preparation of isoquinoline (compound 2)

[0120] 5-(3- Indolyl )-6- methyl -5,6,7,8- Tetrahydro -[1,3] Dioxa [4,5-g] Isoquinoline reacts with 3-chlorobromobenzyl, the same operation 1 Preparation, yield: quantitative. 1 H-NMR (300MHz, CDCl 3 , ppm) δ: 2.35(s, 3H), 2.72(t, 1H), 2.85(t, 1H), 3.18(q, 2H), 4.69(s, 1H), 5.27(s, 2H), 5.80(d , 2H), 6.33(s, 2H), 6.60(s, 1H), 6.92(d, 1H), 7.04(m, 4H), 7.10(m, 1H), 7.22(s, 2H), 7.47(d, 1H, J =7.8); ESI-MS: m / z 431.1 [M+H] + .

Embodiment 3

[0121] Embodiment three: 5-[1-(4 -Chlorobenzyl )-3 -indolyl ]-6- methyl -5,6,7,8- Tetrahydro -[1,3] Dioxa [4,5-g] Preparation of isoquinoline (compound 3)

[0122] Depend on 5-(3- Indolyl )-6- methyl -5,6,7,8- Tetrahydro -[1,3] Dioxa [4,5-g] Prepared by reacting isoquinoline with 4-chlorobromobenzyl, the same operation 1 Preparation, yield: quantitative. 1 H-NMR (600MHz, CDCl 3 , ppm) δ: 2.21(s, 3H), 2.52(t, 1H), 2.72(t, 1H), 3.05(m, 2H), 4.43(s, 1H), 5.18(s, 2H), 5.72(d , 2H), 6.25(s, 1H), 6.52(s, 1H), 6.94(q, 1H), 7.07(t, 1H), 7.11(t, 1H), 7.18(t, 2H), 7.42(d, 1H, J =3.9); ESI-MS: m / z 431.2 [M+H] + .

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Abstract

The invention belongs to the field of synthesis of medicaments, and relates to a 6,7-methylene-dioxy-1,2,3,4-tetrahydroisoquinoline derivative and a preparation method and application thereof, in particular to a 6,7-methylene-dioxy-1,2,3,4-tetrahydroisoquinoline derivative of which sites 1 and 2 are provided with N-substituted indole and the preparation method and application thereof. The general formula of the derivative is shown as the formula (I) in the specification. In-vitro antitumor experiments show that the compound provided by the invention has high activity and high biological activity and can be further researched and developed to be a novel antitumor medicament which is shown as the formula (I) in the specification.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and relates to 6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline derivatives and their preparation methods and applications. It specifically relates to a 6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline derivative with N-substituted indole at the 1 or 2 position, its preparation method and its application in medicine on the application. Background technique [0002] A tumor is a new organism formed by excessive proliferation or abnormal differentiation of mature or developing normal cells in the body under the action of relevant factors, usually forming a mass, hence the name tumor. Tumors are divided into two categories, benign and malignant. Malignant tumors are often called cancer, which is a common and frequently-occurring disease that seriously threatens human health. Today, cancer has become the second leading cause of death in the world. In 2007, about 7.6 million people died of cancer, ac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/056A61K31/475A61P35/00
Inventor 赵冬梅程卯生黄文林宋帅蒋智
Owner SHENYANG PHARMA UNIVERSITY
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