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含呫吨部分的3,3-双（羟基芳基）氧化吲哚和螺环氧化吲哚：合成、机理及生物活性

3,3-Bis(hydroxyaryl)oxindoles and Spirooxindoles Bearing a Xanthene Moiety: Synthesis, Mechanism, and Biological Activity.

作者信息

Steinsits Dániel, Rávai Bettina, Kelemen Zsolt, Hackler László, Vernyik Viktor, Puskás László G, Bálint Erika

机构信息

Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3, H-1111 Budapest, Hungary.

CycloLab Cyclodextrin Research and Development Ltd., Illatos út 7, H-1097 Budapest, Hungary.

出版信息

J Org Chem. 2025 May 16;90(19):6454-6467. doi: 10.1021/acs.joc.5c00270. Epub 2025 May 7.

DOI:10.1021/acs.joc.5c00270
PMID:40331623
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12090213/
Abstract

A facile and efficient methanesulfonic acid-catalyzed, solvent-free, microwave-assisted method was developed for the synthesis of biologically active 3,3-bis(hydroxyaryl)oxindoles and spirooxindoles bearing a xanthene moiety. The scope of the procedure was investigated with a wide range of isatin and phenol derivatives; moreover, the reaction mechanism was studied by density functional theory calculations. Both 3,3-bis(hydroxyaryl)oxindoles and spirooxindoles bearing a xanthene moiety synthesized were evaluated for their anticancer and antimicrobial activity, and most of them showed promising or significant activity on six cancer cell lines and against Gram-positive bacteria.

摘要

开发了一种简便高效的甲磺酸催化、无溶剂、微波辅助的方法，用于合成具有生物活性的含呫吨部分的3,3-双（羟基芳基）氧化吲哚和螺环氧化吲哚。用多种异吲哚酮和苯酚衍生物研究了该方法的适用范围；此外，通过密度泛函理论计算研究了反应机理。对合成的含呫吨部分的3,3-双（羟基芳基）氧化吲哚和螺环氧化吲哚进行了抗癌和抗菌活性评估，其中大多数对六种癌细胞系和革兰氏阳性菌显示出有前景或显著的活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67cf/12090213/a9f2ff740050/jo5c00270_0010.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67cf/12090213/dd7366f8bb34/jo5c00270_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67cf/12090213/7f21cccaffcf/jo5c00270_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67cf/12090213/a48acefb654c/jo5c00270_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67cf/12090213/690f33eebb70/jo5c00270_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67cf/12090213/40b5af589a1d/jo5c00270_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67cf/12090213/a9f2ff740050/jo5c00270_0010.jpg

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