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布洛芬和萘普生的合成新进展。

Recent Advances in the Synthesis of Ibuprofen and Naproxen.

机构信息

Jeju Research Institute of Pharmaceutical Sciences, College of Pharmacy, Jeju National University, 102 Jejudaehak-ro, Jeju 63243, Jeju-do, Korea.

Interdisciplinary Graduate Program in Advanced Convergence Technology & Science, Jeju National University, 102 Jejudaehak-ro, Jeju 63243, Jeju-do, Korea.

出版信息

Molecules. 2021 Aug 7;26(16):4792. doi: 10.3390/molecules26164792.

DOI:10.3390/molecules26164792
PMID:34443379
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8399189/
Abstract

Herein, we review the recent progress in the synthesis of representative nonsteroidal anti-inflammatory drugs (NSAIDs), ibuprofen and naproxen. Although these drugs were discovered over 50 years ago, novel practical and asymmetric approaches are still being developed for their synthesis. In addition, this endeavor has enabled access to more potent and selective derivatives from the key frameworks of ibuprofen and naproxen. The development of a synthetic route to ibuprofen and naproxen over the last 10 years is summarized, including developing methodologies, finding novel synthetic routes, and applying continuous-flow chemistry.

摘要

本文综述了近年来具有代表性的非甾体抗炎药(NSAIDs)布洛芬和萘普生的合成进展。尽管这些药物是在 50 多年前发现的,但仍在不断开发新的实用和不对称方法来合成它们。此外,这一努力还使人们能够从布洛芬和萘普生的关键框架中获得更有效和选择性的衍生物。本文总结了过去 10 年中布洛芬和萘普生合成路线的发展,包括开发方法学、寻找新的合成路线以及应用连续流动化学。

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2
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J Med Chem. 2020 Nov 12;63(21):12614-12622. doi: 10.1021/acs.jmedchem.0c00813. Epub 2020 Oct 26.
3
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4
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6
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Drug Deliv Transl Res. 2024 Nov 20. doi: 10.1007/s13346-024-01737-0.
7
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7
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10
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