核苷类前药ProTides的不对称合成:磷手性中心的构建

doi:10.6023/cjoc202005030

摘要/Abstract

抗病毒药物瑞德西韦正处于临床试验阶段，以验证其对新型冠状病毒的疗效.瑞德西韦是一类结构特殊的前药（prodrug），原先由吉利德公司开发用于埃博拉病的治疗.ProTide （prodrug nucleotide）技术是McGuigan等发展的一种前药设计策略，在抗病毒、抗肿瘤等药物的开发中具有广泛应用.ProTide分子中五价磷原子的手性对药物活性的影响显著.因此，此类结构的高效不对称合成引起了学术界和工业界的广泛兴趣.归纳了近年来ProTide立体选择性偶联方法的新进展，分两类分别进行综述，即使用光学纯P（V）前体的反应和使用消旋的P（V）前体的反应.包括（动态）动力学拆分在内的多种策略被用于构建此类磷手性中心，其中一些合成方法可实现千克规模的制备.还总结了光学纯磷酰胺前体的不对称合成方法.此外，对一些代表性的ProTide试验药物的临床表现，也做了简要讨论.

关键词: 抗病毒, 不对称合成, 核苷类似物, ProTide, 磷中心手性

As an antivirus drug, remdesivir is currently in clinical studies for the treatment of COVID-19. Remdesivir is a prodrug originally developed by Gilead for the treatment of Ebola. The prodrug nucleotide (ProTide) technology is a prodrug-designing strategy developed by McGuigan and co-workers, in which a phosphoramidate side-chain is covalently attached to the hydroxy group of a drug molecule in order to enhance the cell permeability and metabolic activation efficiency. This approach has proved to be very successful in the identification of nucleoside analogues with antiviral or antitumor activities. It is also adapted in the application of non-nucleoside agents, such as neurodegeneration therapeutics, further demonstrating its usefulness in drug discovery. The chirality of the pentavalent phosphorous plays a significant role in the bioactivity of a ProTide molecule. Therefore, the efficient synthesis of such chemical scaffold in a highly enantioselective manner is very desirable and has intrigued great interests from both academia and pharmaceutical industry. In this review, based on the reactions employing optically pure P(V) precursors or P-racemic P(V) precursors, the recent advances on the stereoselective assembly of ProTide compounds are summarized. Various innovative strategies, including (dynamic) kinetic resolutions, were implemented to construct the vital P-stereogenic center with high regio- and stereo-selectivity. It is notable that several methods could be performed at kilogram scale, which are highlighted to showcase their practical values in the process chemistry. The asymmetric synthesis of enantiopure phosphoramidate precursors is illustrated in detail which will be informative for future drug development. Moreover, the clinical performance of some investigational ProTide drugs is also briefly discussed.

Key words: antiviral, asymmetric synthesis, nucleoside analogue, prodrug nucleotide (ProTide), P-stereogenic center

引用此文

刘祎辰, 程杰飞, 洪然. 核苷类前药ProTides的不对称合成:磷手性中心的构建[J]. 有机化学, 2020, 40(10): 3237-3248.

Liu Yichen, Cheng Jiefei, Hong Ran. Asymmetric Synthesis of Prodrug Nucleotides (ProTides): Construction of the P-Stereogenic Centers[J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3237-3248.

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