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2-(3',4',5'-三甲氧基苯甲酰基)-3-N,N-二甲基氨基苯并[b]呋喃衍生物作为微管蛋白聚合抑制剂的合成及生物学评价

Synthesis and biological evaluation of 2-(3',4',5'-trimethoxybenzoyl)-3-N,N-dimethylamino benzo[b]furan derivatives as inhibitors of tubulin polymerization.

作者信息

Romagnoli Romeo, Baraldi Pier Giovanni, Sarkar Taradas, Carrion Maria Dora, Cruz-Lopez Olga, Lopez Cara Carlota, Tolomeo Manlio, Grimaudo Stefania, Di Cristina Antonietta, Pipitone Maria Rosaria, Balzarini Jan, Gambari Roberto, Ilaria Lampronti, Saletti Roberto, Brancale Andrea, Hamel Ernest

机构信息

Dipartimento di Scienze Farmaceutiche, Università di Ferrara, Via Fossato di Mortara 17-19, 44100 Ferrara, Italy.

出版信息

Bioorg Med Chem. 2008 Sep 15;16(18):8419-26. doi: 10.1016/j.bmc.2008.08.029. Epub 2008 Aug 17.

DOI:10.1016/j.bmc.2008.08.029
PMID:18755591
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2574800/
Abstract

Molecules that target microtubules have an important role in the treatment of cancer. A new class of inhibitors of tubulin polymerization based on the 2-(3,4,5-trimethoxybenzoyl)-2-dimethylamino-benzo[b]furan molecular skeleton was synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization, and cell cycle effects. The most promising compound in this series was 2-(3,4,5-trimethoxybenzoyl)-3-dimethylamino-6-methoxy-benzo[b]furan, which inhibits cancer cell growth at nanomolar concentrations and interacts strongly with tubulin by binding to the colchicine site.

摘要

靶向微管的分子在癌症治疗中具有重要作用。基于2-(3,4,5-三甲氧基苯甲酰基)-2-二甲基氨基苯并[b]呋喃分子骨架，合成了一类新型微管蛋白聚合抑制剂，并对其抗增殖活性、微管蛋白聚合抑制作用和细胞周期效应进行了评估。该系列中最有前景的化合物是2-(3,4,5-三甲氧基苯甲酰基)-3-二甲基氨基-6-甲氧基苯并[b]呋喃，它在纳摩尔浓度下就能抑制癌细胞生长，并通过与秋水仙碱结合位点结合而与微管蛋白强烈相互作用。

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本文引用的文献

1
Benzoylurea derivatives as a novel class of antimitotic agents: synthesis, anticancer activity, and structure-activity relationships.作为一类新型抗有丝分裂剂的苯甲酰脲衍生物：合成、抗癌活性及构效关系
J Med Chem. 2008 Jun 12;51(11):3094-103. doi: 10.1021/jm070890u. Epub 2008 May 6.
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Synthesis and biological evaluation of 1-methyl-2-(3',4',5'-trimethoxybenzoyl)-3-aminoindoles as a new class of antimitotic agents and tubulin inhibitors.新型抗有丝分裂剂和微管蛋白抑制剂1-甲基-2-(3',4',5'-三甲氧基苯甲酰基)-3-氨基吲哚的合成及生物学评价
J Med Chem. 2008 Mar 13;51(5):1464-8. doi: 10.1021/jm7011547. Epub 2008 Feb 9.
3
Targeting microtubules to inhibit angiogenesis and disrupt tumour vasculature: implications for cancer treatment.靶向微管以抑制血管生成并破坏肿瘤脉管系统：对癌症治疗的意义
Curr Cancer Drug Targets. 2007 Sep;7(6):566-81. doi: 10.2174/156800907781662266.
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Synthesis and biological evaluation of 2- and 3-aminobenzo[b]thiophene derivatives as antimitotic agents and inhibitors of tubulin polymerization.2-和3-氨基苯并[b]噻吩衍生物作为抗有丝分裂剂和微管蛋白聚合抑制剂的合成及生物学评价
J Med Chem. 2007 May 3;50(9):2273-7. doi: 10.1021/jm070050f. Epub 2007 Apr 10.
5
Recent progress in discovery and development of antimitotic agents.抗有丝分裂药物发现与开发的最新进展。
Anticancer Agents Med Chem. 2007 Mar;7(2):189-208. doi: 10.2174/187152007780058650.
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Current development status of small-molecule vascular disrupting agents.小分子血管破坏剂的当前发展状况。
Curr Opin Investig Drugs. 2006 Jun;7(6):522-8.
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Medicinal chemistry of combretastatin A4: present and future directions.秋水仙素A4的药物化学：现状与未来方向
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Antimitotic agents of natural origin.天然来源的抗有丝分裂剂。
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Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain.从与秋水仙碱和类微管相关蛋白结构域的复合物中洞察微管蛋白调控机制。
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