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天然产物结构修饰中的异恶唑/异恶唑啉骨架:综述

Isoxazole/Isoxazoline Skeleton in the Structural Modification of Natural Products: A Review.

作者信息

Wang Xiyue, Hu Qingyun, Tang Hui, Pan Xinhui

机构信息

Laboratory of Xinjiang Phytomedicine Resource and Utilization, Ministry of Education, School of Pharmaceutical Sciences, Shihezi University, Shihezi 832002, China.

出版信息

Pharmaceuticals (Basel). 2023 Feb 2;16(2):228. doi: 10.3390/ph16020228.

DOI:10.3390/ph16020228
PMID:37259376
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9964809/
Abstract

Isoxazoles and isoxazolines are five-membered heterocyclic molecules containing nitrogen and oxygen. Isoxazole and isoxazoline are the most popular heterocyclic compounds for developing novel drug candidates. Over 80 molecules with a broad range of bioactivities, including antitumor, antibacterial, anti-inflammatory, antidiabetic, cardiovascular, and other activities, were reviewed. A review of recent studies on the use of isoxazoles and isoxazolines moiety derivative activities for natural products is presented here, focusing on the parameters that affect the bioactivity of these compounds.

摘要

异恶唑和异恶唑啉是含有氮和氧的五元杂环分子。异恶唑和异恶唑啉是开发新型候选药物最常用的杂环化合物。本文综述了80多种具有广泛生物活性的分子,包括抗肿瘤、抗菌、抗炎、抗糖尿病、心血管等活性。本文介绍了对异恶唑和异恶唑啉部分衍生物活性在天然产物中应用的最新研究综述,重点关注影响这些化合物生物活性的参数。

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Angew Chem Int Ed Engl. 2025 Sep 8;64(37):e202509658. doi: 10.1002/anie.202509658. Epub 2025 Aug 1.
4
Unveiling Hydrogen Bonding and Solvent Effects on Directed Nitrile Oxide [3 + 2] Cycloaddition Reactions: Selectivity of 2,2-Dimethylpropane Nitrile Oxide with Cyclopentenylbenzamide: An MEDT Study.揭示氢键和溶剂对定向腈氧化物[3 + 2]环加成反应的影响:2,2-二甲基丙烷腈氧化物与环戊烯基苯甲酰胺的选择性:一项分子中的电子密度拓扑研究
ACS Omega. 2025 Apr 3;10(14):13868-13879. doi: 10.1021/acsomega.4c07794. eCollection 2025 Apr 15.
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Bioactivity of novel isoxazole-fused heterocycles: comprehensive antimicrobial, antioxidant activities, SwissADME predictions, molecular docking, and DFT analysis.新型异恶唑稠合杂环的生物活性:综合抗菌、抗氧化活性、SwissADME预测、分子对接和密度泛函理论分析
Mol Divers. 2025 Apr 17. doi: 10.1007/s11030-025-11180-z.
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Studies of the Synthesis of Fused Isoxazoline/Isoquinolinones and Evaluation of the Antifungal Activity of Isoxazole-like Benzamide and Isoquinolinone Hybrids.稠合异恶唑啉/异喹啉酮的合成研究以及异恶唑类苯甲酰胺和异喹啉酮杂化物的抗真菌活性评估。
Molecules. 2025 Jan 27;30(3):589. doi: 10.3390/molecules30030589.
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In Silico Exploration of Isoxazole Derivatives of Usnic Acid: Novel Therapeutic Prospects Against α-Amylase for Diabetes Treatment.乌苏烷酸异恶唑衍生物的计算机探索:治疗糖尿病的新型α-淀粉酶治疗靶点
Cell Biochem Biophys. 2024 Dec;82(4):3351-3366. doi: 10.1007/s12013-024-01419-1. Epub 2024 Jul 17.
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Acridine-Isoxazole and Acridine-Azirine Hybrids: Synthesis, Photochemical Transformations in the UV/Visible Radiation Boundary Region, and Anticancer Activity.吖啶-异恶唑和吖啶-氮丙啶杂化物:合成、紫外/可见辐射边界区域的光化学转化及抗癌活性
Molecules. 2024 Mar 29;29(7):1538. doi: 10.3390/molecules29071538.
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A Convenient Synthesis of Novel Isoxazolidine and Isoxazole Isoquinolinones Fused Hybrids.新型异恶唑烷和异恶唑并异喹啉酮稠合杂化物的简便合成
Molecules. 2023 Dec 22;29(1):91. doi: 10.3390/molecules29010091.
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3-[-Bis(sulfonyl)amino]isoxazolines with Spiro-Annulated or 1,2-Annulated Cyclooctane Rings Inhibit Reproduction of Tick-Borne Encephalitis, Yellow Fever, and West Nile Viruses.含螺环或 1,2-并环[环辛烷]的 3-[双(磺酰基)氨基]异恶唑啉类化合物抑制蜱传脑炎、黄热病和西尼罗河病毒的复制。
Int J Mol Sci. 2023 Jun 28;24(13):10758. doi: 10.3390/ijms241310758.
新型蛇床子素异噁唑啉衍生物的设计、合成与生物评价作为杀虫剂候选物。
J Agric Food Chem. 2022 Jul 6;70(26):7921-7928. doi: 10.1021/acs.jafc.2c01925. Epub 2022 Jun 22.
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Exploration of Isoxazole-Carboxylic Acid Methyl Ester Based 2-Substituted Quinoline Derivatives as Promising Antitubercular Agents.探索基于异恶唑羧酸甲酯的 2-取代喹啉衍生物作为有前途的抗结核药物。
Chem Biodivers. 2022 Jul;19(7):e202200324. doi: 10.1002/cbdv.202200324. Epub 2022 Jun 23.
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Design, synthesis, evaluation of new 3-acetylisoxazolines and their hybrid analogous as anticancer agents: In vitro and in silico analysis.设计、合成、评价新型 3-乙酰异恶唑啉及其杂合类似物的抗癌活性:体外和计算分析。
Comput Biol Chem. 2022 Jun;98:107666. doi: 10.1016/j.compbiolchem.2022.107666. Epub 2022 Mar 24.
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Chemical profiling, cytotoxic activities through apoptosis induction in human fibrosarcoma and carcinoma cells, and molecular docking of some 1,2,3-triazole-isoxazoline hybrids using the eugenol as a precursors.利用丁香酚作为前体,对一些 1,2,3-三唑异恶唑啉类化合物进行化学分析、通过诱导人纤维肉瘤和癌细胞凋亡进行细胞毒性活性研究,以及分子对接。
J Biomol Struct Dyn. 2023 Apr;41(7):2759-2771. doi: 10.1080/07391102.2022.2037466. Epub 2022 Feb 17.
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Design, synthesis, and insecticidal and fungicidal activities of quaternary ammonium salt derivatives of a triazolyphenyl isoxazoline insecticide.三唑基苯基异恶唑啉杀虫剂季铵盐衍生物的设计、合成及其杀虫和杀菌活性
Pest Manag Sci. 2022 May;78(5):2011-2021. doi: 10.1002/ps.6824. Epub 2022 Feb 19.
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A Study on Synthesis of Chalcone Derived -5- Membered Isoxazoline and Isoxazole Scaffolds.查尔酮衍生的五元异噁唑啉和异噁唑骨架的合成研究。
Curr Org Synth. 2022 Aug 6;19(5):643-663. doi: 10.2174/1570179419666220127143141.
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Biological, toxicological and molecular docking evaluations of isoxazoline-thiazolidine-2,4-dione analogues as new class of anti-hyperglycemic agents.异恶唑啉-噻唑烷-2,4-二酮类似物作为新型抗高血糖药物的生物学、毒理学及分子对接评估
J Biomol Struct Dyn. 2023 Feb;41(3):1072-1084. doi: 10.1080/07391102.2021.2017348. Epub 2021 Dec 26.
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Harmine Hydrochloride Mediates the Induction of G2/M Cell Cycle Arrest in Breast Cancer Cells by Regulating the MAPKs and AKT/FOXO3a Signaling Pathways.盐酸去氢骆驼蓬碱通过调控 MAPKs 和 AKT/FOXO3a 信号通路诱导乳腺癌细胞 G2/M 期细胞周期阻滞。
Molecules. 2021 Nov 5;26(21):6714. doi: 10.3390/molecules26216714.