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微波辅助合成含氮杂环在药物化学中的益处及应用

Benefits and applications of microwave-assisted synthesis of nitrogen containing heterocycles in medicinal chemistry.

作者信息

Henary Maged, Kananda Carl, Rotolo Laura, Savino Brian, Owens Eric A, Cravotto Giancarlo

机构信息

Department of Chemistry, Georgia State University 100 Piedmont Ave SE Atlanta Georgia 30303 USA

Center for Diagnostics and Therapeutics, Georgia State University 100 Piedmont Ave SE Atlanta Georgia 30303 USA.

出版信息

RSC Adv. 2020 Apr 7;10(24):14170-14197. doi: 10.1039/d0ra01378a. eCollection 2020 Apr 6.

Abstract

Nitrogen containing heterocycles are of immense research interest because they are often found as naturally occurring bioactive compounds. The prominence of N-heterocycles makes it vital to develop methods to increase their synthetic efficiencies and probe the effects of their modifications on biological efficacy. Medicinal chemists have exploited microwave-assisted organic synthesis (MAOS) to facilitate the development of complex heterocyclic structures. MAOS is a growing synthetic methodology among medicinal chemists and has proven to be more efficient in terms of reaction yield, reaction time, product purity and environmental friendliness for many reactions when compared to conventional thermal methods for cycloaddition and selective functionalization. The importance of nitrogen containing ring systems in medicine cannot be understated, as such ring systems have shown to be applicable in compounds such as vitamins, herbicides, anti-fungal agents, anti-bacterial agents and anti-cancer agents, among other things. The significance of these applications has created an unprecedented need for more efficient synthetic methods. This review presents an overview of MAOS and its role in recent and pressing advancements for the synthesis of small- and medium-sized nitrogen containing heterocycles, including pyrroles, indoles, pyridines, pyrrolidines, imidazoles, pyrazoles, pyrazolines, lactams, and 1,2,3-triazoles, which are significant scaffolds for compounds with medicinal uses.

摘要

含氮杂环化合物具有极大的研究价值,因为它们常作为天然存在的生物活性化合物被发现。氮杂环化合物的重要性使得开发提高其合成效率的方法以及探究其修饰对生物活性的影响变得至关重要。药物化学家利用微波辅助有机合成(MAOS)来促进复杂杂环结构的开发。MAOS在药物化学家中是一种不断发展的合成方法,并且与传统的热环加成和选择性官能化方法相比,已被证明在许多反应的反应产率、反应时间、产物纯度和环境友好性方面更有效。含氮环系统在医学中的重要性不容小觑,因为这类环系统已被证明可应用于维生素、除草剂、抗真菌剂、抗菌剂和抗癌剂等化合物中。这些应用的重要性引发了对更高效合成方法前所未有的需求。本综述概述了MAOS及其在近期和迫切需要的中小型含氮杂环化合物合成进展中的作用,这些杂环化合物包括吡咯、吲哚、吡啶、吡咯烷、咪唑、吡唑、吡唑啉、内酰胺和1,2,3 - 三唑,它们是具有药用价值化合物的重要骨架。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7035/9051880/10c56b9ad3b2/d0ra01378a-f1.jpg

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