Synthesis of Polyoxygenated 4,5-Diarylpyridazines with Antiproliferative and Antitubulin Activity via Inverse Electron-Demand Diels-Alder Reaction of 1,2,4,5- Tetrazine#

IF 1.7 3区化学 Q3 CHEMISTRY, ORGANIC

Current Organic Chemistry Pub Date : 2024-07-04 DOI:10.2174/0113852728314401240613045216

Olga I. Adaeva, Dmitry V. Demchuk, Roman A. Dolotov, Tatiana S. Kuptsova, Marina N. Semenova, Victor V. Semenov

引用次数: 0

Abstract

: The synthesis of a series of multifunctionalized 4,5-diarylpyridazines via inverse electron-demand Diels-Alder reaction between highly oxygenated diarylacetylenes and unsubstituted 1,2,4,5-tetrazine was developed using polyalkoxybenzenes isolated from industrial essential oils as starting material. The reaction proceeded smoothly to afford combretastatin A-4 analogs with pyridazine linker in consistently high yield. In a phenotypic sea urchin embryo assay, diarylpyridazine with 3,4,5-trimethoxyphenyl and 3-amino-4- methoxyphenyl aryl rings was identified as a potent antimitotic microtubule-destabilizing compound.

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通过 1,2,4,5- 四嗪的逆电子需求 Diels-Alder 反应合成具有抗增殖和抗微管蛋白活性的多氧合 4,5-Diarylpyridazines #

:以从工业精油中分离出的多烷氧基苯为起始原料，通过高含氧二芳基乙炔与未取代的 1,2,4,5- 四嗪之间的反电子需求 Diels-Alder 反应，合成了一系列多功能 4,5- 二芳基哒嗪。反应顺利进行，以持续的高产率获得了带有哒嗪连接物的考布他丁 A-4 类似物。在表型海胆胚胎试验中，具有 3,4,5-三甲氧基苯基和 3-氨基-4-甲氧基苯基芳基环的哒嗪被鉴定为一种有效的抗畸形微管破坏化合物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Current Organic Chemistry 化学-有机化学

CiteScore

3.70

自引率

7.70%

发文量

审稿时长

1 months

期刊介绍： Current Organic Chemistry aims to provide in-depth/mini reviews on the current progress in various fields related to organic chemistry including bioorganic chemistry, organo-metallic chemistry, asymmetric synthesis, heterocyclic chemistry, natural product chemistry, catalytic and green chemistry, suitable aspects of medicinal chemistry and polymer chemistry, as well as analytical methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by chosen experts who are internationally known for their eminent research contributions. The Journal also accepts high quality research papers focusing on hot topics, highlights and letters besides thematic issues in these fields. Current Organic Chemistry should prove to be of great interest to organic chemists in academia and industry, who wish to keep abreast with recent developments in key fields of organic chemistry.

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