膦催化[4 + 1]环构建3-氧- 3h -螺[苯并呋喃-2,1 ' -环戊烷]羧酸衍生物及其抗纤维化生物学评价

IF 3 3区医学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Bioorganic & Medicinal Chemistry Pub Date : 2025-04-09 DOI:10.1016/j.bmc.2025.118192

Sheng-Hong Li , Feng-Yi Lu , Muralikrishna Katta, Yun-Yun Liu, Danling Huang, Yong-Xian Cheng

{"title":"膦催化[4 + 1]环构建3-氧- 3h -螺[苯并呋喃-2,1 ' -环戊烷]羧酸衍生物及其抗纤维化生物学评价","authors":"Sheng-Hong Li , Feng-Yi Lu , Muralikrishna Katta, Yun-Yun Liu, Danling Huang, Yong-Xian Cheng","doi":"10.1016/j.bmc.2025.118192","DOIUrl":null,"url":null,"abstract":"<div><div>A novel phosphine-catalyzed [4 + 1] cyclization reaction was developed to construct the 3-oxo-3<em>H</em>-spiro[benzofuran-2,1′-cyclopentane] scaffold. Utilizing this innovative method, twenty diverse 3-oxo-3<em>H</em>-spiro[benzofuran-2,1′-cyclopentane] carboxylic acid derivatives were synthesized and evaluated for their anti-fibrotic activities. Compound <strong>L10-P1</strong> possessed potential anti-fibrotic activity by inhibiting the expression of fibronectin, collagen I, and α-SMA. This study presents a new synthetic route for 3<em>H</em>-spiro[benzofuran-2,1′<em>-</em>cyclopentan]-3-one derivatives, contributing valuable insights into the chemical and biological diversity of these compounds.</div></div>","PeriodicalId":255,"journal":{"name":"Bioorganic & Medicinal Chemistry","volume":"124 ","pages":"Article 118192"},"PeriodicalIF":3.0000,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Construction of 3-oxo-3H-spiro[benzofuran-2,1′-cyclopentane] carboxylic acid derivatives via phosphine-catalyzed [4 + 1] annulations and their biological evaluation against fibrosis\",\"authors\":\"Sheng-Hong Li , Feng-Yi Lu , Muralikrishna Katta, Yun-Yun Liu, Danling Huang, Yong-Xian Cheng\",\"doi\":\"10.1016/j.bmc.2025.118192\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A novel phosphine-catalyzed [4 + 1] cyclization reaction was developed to construct the 3-oxo-3<em>H</em>-spiro[benzofuran-2,1′-cyclopentane] scaffold. Utilizing this innovative method, twenty diverse 3-oxo-3<em>H</em>-spiro[benzofuran-2,1′-cyclopentane] carboxylic acid derivatives were synthesized and evaluated for their anti-fibrotic activities. Compound <strong>L10-P1</strong> possessed potential anti-fibrotic activity by inhibiting the expression of fibronectin, collagen I, and α-SMA. This study presents a new synthetic route for 3<em>H</em>-spiro[benzofuran-2,1′<em>-</em>cyclopentan]-3-one derivatives, contributing valuable insights into the chemical and biological diversity of these compounds.</div></div>\",\"PeriodicalId\":255,\"journal\":{\"name\":\"Bioorganic & Medicinal Chemistry\",\"volume\":\"124 \",\"pages\":\"Article 118192\"},\"PeriodicalIF\":3.0000,\"publicationDate\":\"2025-04-09\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Bioorganic & Medicinal Chemistry\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0968089625001336\",\"RegionNum\":3,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Bioorganic & Medicinal Chemistry","FirstCategoryId":"3","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0968089625001336","RegionNum":3,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}

引用次数: 0

摘要

建立了一种新的膦催化[4 + 1]环化反应，构建了3-氧- 3h -螺[苯并呋喃-2,1 ' -环戊烷]支架。利用这种创新的方法，合成了20种不同的3-氧- 3h -螺[苯并呋喃-2,1 ' -环戊烷]羧酸衍生物，并对其抗纤维化活性进行了评价。化合物L10-P1通过抑制纤维连接蛋白、I型胶原和α-SMA的表达而具有潜在的抗纤维化活性。本研究提出了一种新的3h -螺[苯并呋喃-2,1 ' -环戊烷]-3- 1衍生物的合成路线，为这些化合物的化学和生物多样性提供了有价值的见解。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Construction of 3-oxo-3H-spiro[benzofuran-2,1′-cyclopentane] carboxylic acid derivatives via phosphine-catalyzed [4 + 1] annulations and their biological evaluation against fibrosis

查看原文本刊更多论文

Construction of 3-oxo-3H-spiro[benzofuran-2,1′-cyclopentane] carboxylic acid derivatives via phosphine-catalyzed [4 + 1] annulations and their biological evaluation against fibrosis

A novel phosphine-catalyzed [4 + 1] cyclization reaction was developed to construct the 3-oxo-3H-spiro[benzofuran-2,1′-cyclopentane] scaffold. Utilizing this innovative method, twenty diverse 3-oxo-3H-spiro[benzofuran-2,1′-cyclopentane] carboxylic acid derivatives were synthesized and evaluated for their anti-fibrotic activities. Compound L10-P1 possessed potential anti-fibrotic activity by inhibiting the expression of fibronectin, collagen I, and α-SMA. This study presents a new synthetic route for 3H-spiro[benzofuran-2,1′-cyclopentan]-3-one derivatives, contributing valuable insights into the chemical and biological diversity of these compounds.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Bioorganic & Medicinal Chemistry 医学-生化与分子生物学

CiteScore

6.80

自引率

2.90%

发文量

413

审稿时长

17 days

期刊介绍： Bioorganic & Medicinal Chemistry provides an international forum for the publication of full original research papers and critical reviews on molecular interactions in key biological targets such as receptors, channels, enzymes, nucleotides, lipids and saccharides. The aim of the journal is to promote a better understanding at the molecular level of life processes, and living organisms, as well as the interaction of these with chemical agents. A special feature will be that colour illustrations will be reproduced at no charge to the author, provided that the Editor agrees that colour is essential to the information content of the illustration in question.