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Microtubule inhibitor as well as preparation method and application thereof

A compound and alkyl technology, applied in the field of microtubule inhibitors and its preparation, can solve problems such as easy conversion to trans conformation, decreased biological activity, etc.

Active Publication Date: 2018-08-17
WEST VAC BIOPHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The object of the present invention is to provide a microtubule inhibitor and its preparation method and use, so as to solve the problem that the existing microtubule inhibitor CA-4 cis conformation is easily converted into a trans conformation, resulting in a sharp decline in biological activity

Method used

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  • Microtubule inhibitor as well as preparation method and application thereof
  • Microtubule inhibitor as well as preparation method and application thereof
  • Microtubule inhibitor as well as preparation method and application thereof

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Embodiment 1

[0131] The synthesis of embodiment 1 compound of the present invention

[0132] 1. General description of the synthetic scheme

[0133] The present invention synthesizes 1,4-substituted-3-(3,4,5-trimethoxyphenyl)-5-aminopyrazole analogs 6a1-6d4 through five steps of chemical reactions (synthetic route 1). First, after the initial raw material 3,4,5-trimethoxybenzoic acid methyl esterification, compound 2 is obtained; then sodium hydride is used as the base, acetonitrile-tetrahydrofuran is used as the solvent, and the compound 3 obtained by reflux reaction; further with the corresponding hydrazine ( Methylhydrazine, tert-butylhydrazine, p-fluorophenylhydrazine and p-methoxyphenylhydrazine) react to form pyrazole ring compounds 4a-4d through ring closure; next, after NBS (N-Bromosuccinimide, N-bromobutyl Diimide) bromination reaction to obtain important intermediates 5a-5d; then by Suzuki reaction, that is, with Cs 2 CO 3 as base, PdCl 2 (PPh 3 ) 2 As a catalyst, 1,2-ethyl...

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Abstract

The invention relates to a microtubule inhibitor as well as a preparation method and application thereof, belongs to the field of chemical medicines and aims to solve the problem that the biological activity is rapidly reduced because the existing microtubule inhibitor CA-4 cisoid conformation is easily transformed into trans-conformation. The technical scheme provides a compound expressed by a formula I as well as pharmaceutically acceptable salts or crystals thereof. Experiment results show that the compound shows extremely strong in-vitro anti-proliferation activity in tumor cells such as ovarian cancer cells, cervical cancer cells, non-small cell lung cancer cells, colon cancer cells and breast cancer cells, can obviously inhibit the tumor progression in the body, and is high in safety; the formula I is as shown in the description.

Description

technical field [0001] The invention relates to a microtubule inhibitor, a preparation method and application thereof, and belongs to the field of chemical medicine. Background technique [0002] Microtubules are composed of α- and β-tubulin dimers and are an important part of the cytoskeleton. Microtubules have a wide range of important roles, including cell division, signal transduction, cell fluidity, maintenance of cell shape, and intracellular vesicle transport, among others. Therefore, microtubules have become attractive targets for antitumor drugs. The assembly and disassembly of α- and β-tubulin dimers is a kinetic equilibrium process. A number of molecules capable of disrupting this balance have been developed as microtubule inhibitors. These microtubule inhibitors mainly function by binding to one of the three binding sites in β-tubulin. For example, paclitaxel acts as a microtubule stabilizer by binding to taxane sites, and vincristine binds to vincristine sit...

Claims

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Application Information

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IPC IPC(8): C07D231/38C07D231/12A61P35/00
CPCA61P35/00C07D231/12C07D231/38
Inventor 赖钦淮陈浩苏小兰王誉熹姚于勤杨金亮
Owner WEST VAC BIOPHARMA CO LTD
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