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依诺沙星类化合物的合成及生物应用进展。

Advances in the Synthesis and Biological Applications of Enoxacin-Based Compounds.

机构信息

Euromed Research Center, School of Engineering in Biomedical and Biotechnology, Euromed University of Fes (UEMF), Fez 30000, Morocco.

Institut de Chimie Organique et Analytique, Université d'Orléans, UMR CNRS 7311, BP 6759, CEDEX 2, 45067 Orléans, France.

出版信息

Biomolecules. 2024 Nov 7;14(11):1419. doi: 10.3390/biom14111419.

DOI:10.3390/biom14111419
PMID:39595595
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11592230/
Abstract

A comprehensive review of advances in the synthesis and biological applications of enoxacin (1, referred to as ENX)-based compounds is presented. ENX, a second-generation fluoroquinolone (FQ), is a prominent 1,8-naphthyridine containing compounds studied in medicinal chemistry. Quinolones, a class of synthetic antibiotics, are crucial building blocks for designing multi-biological libraries due to their inhibitory properties against DNA replication. Chemical modifications at positions 3 and 7 of the quinolone structure can transform antibacterial FQs into anticancer analogs. ENX and its derivatives have been examined for various therapeutic applications, including anticancer, antiviral, and potential treatment against COVID-19. Several synthetic methodologies have been devised for the efficient and versatile synthesis of ENX and its derivatives. This review emphasizes all-inclusive developments in the synthesis of ENX derivatives, focusing on modifications at C3 (carboxylic acid, Part A), C7 (piperazinyl, Part B), and other modifications (Parts A and B). The reactions considered were chosen based on their reproducibility, ease of execution, accessibility, and the availability of the methodology reported in the literature. This review provides valuable insights into the medicinal properties of these compounds, highlighting their potential as therapeutic agents in various fields.

摘要

本文全面综述了依诺沙星（1，简称 ENX）为基础的化合物的合成和生物应用方面的进展。ENX 是第二代氟喹诺酮（FQ）类药物，是药物化学中研究的一种重要的 1,8-萘啶化合物。喹诺酮类是一类合成抗生素，由于其对 DNA 复制的抑制作用，是设计多生物学文库的重要构建块。喹诺酮结构 3 位和 7 位的化学修饰可以将抗菌 FQ 转化为抗癌类似物。ENX 及其衍生物已被研究用于各种治疗应用，包括抗癌、抗病毒以及 COVID-19 的潜在治疗。已经设计了几种合成方法来高效和多功能地合成 ENX 和其衍生物。本文重点综述了 ENX 衍生物的全合成发展，侧重于 C3（羧酸，A 部分）、C7（哌嗪基，B 部分）和其他修饰（A 部分和 B 部分）的修饰。选择考虑的反应是基于它们的重现性、执行的容易程度、可及性以及文献中报道的方法的可用性。本文综述提供了对这些化合物的药用性质的深入了解，强调了它们作为各种领域治疗剂的潜力。

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