Two types of isoquinoline compounds and application thereof to preparing anti-cancer medicaments

An anti-cancer drug, the technology of isoquinoline, is applied in the direction of boron compound active ingredient, compound containing periodic table Group 3/13 elements, anti-tumor drug, etc. Research reports on cancer activity, literature reports on unseen structures and synthesis, etc.

Inactive Publication Date: 2012-08-08
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, so far, there is no research report on the biological activities (including anticancer activities) of class A and class B compounds
Simultaneously, all B class compounds involved in the present invention are new compounds, and there is no bibliographical report about its structure and synthesis

Method used

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  • Two types of isoquinoline compounds and application thereof to preparing anti-cancer medicaments
  • Two types of isoquinoline compounds and application thereof to preparing anti-cancer medicaments
  • Two types of isoquinoline compounds and application thereof to preparing anti-cancer medicaments

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Embodiment Construction

[0014] In the present invention, applicants designed and synthesized N-aryl-3,4-dihydroisoquinolinate (A series) and 1-cyano or alkoxy-N-aryl-1,2,3 , The general structural formula of 4-tetrahydroisoquinoline compound (B series) is as follows:

[0015]

[0016] Among them, R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 are the same or different hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, unsaturated monocyclic hydrocarbon, alkoxy, halogen, hydroxyl, nitro, cyano, trifluoromethyl, heterocycle substituent, carboxyl, ester, amide, acyl or aldehyde;

[0017] R 6 is an aliphatic or aryl group;

[0018] R 13 Is cyano (—CN) or alkoxyl (RO—);

[0019] x - Sulfate, halide anion, carbonate, bicarbonate, phosphate, hydrogen phosphate, fatty acid, sulfonate or tetraphenylborate.

[0020] The invention established for the preparation of N-aryl-3,4-dihydroisoquinolinate (A series) and 1-cyano or alkoxy-N-aryl-1,2,3,4-tetra The typical synthetic ro...

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Abstract

The invention relates to two types of isoquinoline compounds and application thereof to preparing anti-cancer medicaments. The compounds have obvious growth suppression and activity killing effects on various human cancer cells. The two types of isoquinoline compounds have the molecular structural characteristics shown in the specification respectively, wherein R1, R2, R3, R4, R5, R7, R8, R9, R10, R11 and R12 are same or different hydrogen, alkyl group, naphthenic group, alkenyl group, alkine group, unsaturated monocyclic alkyl group, alkoxy group, halogen, hydroxyl group, nitryl group, cyano group, trifluoromethyl group, heterocyclic substituent, carboxyl group, ester group, amido group, acryl group or aldehyde group; R6 is an aliphatic hydrocarbon group or aryl group; R13 is cyano (-CH) or alkoxy (RO-); and X- is sulfate radical, halogen anion, carbonate, bicarbonate radical, phosphate radical, hydrogen phosphate radical, fatty acid radical, sulfonic acid radical or tetraphenyl borate radical.

Description

1. Technical field: [0001] The invention relates to two types of isoquinoline compounds with brand new structures, in particular to two types of isoquinoline compounds and their application as preparation of anticancer drugs. 2. Background technology: [0002] In many plants, there is a class of natural alkaloids with important pharmacological activities, that is, quaternary ammonium benzophenanthridine compounds (quaternary benzo[ c ]phenanthridine alkaloids, QBAs). For example, sanguinarine, chelerythrine, sanguilutine, chelirubine, chelilutine, sangrirubine, nitidine, fagaronine, etc. Pharmacological activity studies have proved that quaternary ammonium benzophenanthridine compounds have significant antitumor and antimicrobial activities, and the iminium salt (—C=N + -) structure is its main active group. However, the chemical properties of natural QBAs are relatively active, and it is easy to interact with many nucleophiles (such as OH - 、CN - , NH 3 , amines, alco...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/26C07D217/16C07F5/02A61K31/472A61K31/69A61P35/00
Inventor 周乐苗芳曹芳君杨新娟
Owner NORTHWEST A & F UNIV
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