Direct Arylation of Juglone Enables Divergent Access to WS-5995 Analogs.

IF 1.5 4区医学 Q4 CHEMISTRY, MEDICINAL

Chemical & pharmaceutical bulletin Pub Date : 2026-01-01 DOI:10.1248/cpb.c26-00475

Yusuke Akagi, Yoshimi Shimizu, Erika Iwasaki, Yuichiro Taira, Toshiya Komatsu

引用次数: 0

Abstract

The direct arylation of juglone enables concise access to WS-5995A and the related natural product WS-5995C, providing an entry to the WS-5995 family. The method affords access to lactam analogs via either C-2 or C-3 arylation, enabling the variation of the phenolic hydroxyl position. Cytotoxicity studies reveal a pronounced effect of the phenolic hydroxyl group positioning on biological activity, with the C-3-derived lactam showing enhanced potency. Further demethylation of WS-5995A increases activity, suggesting an important role of a free phenolic hydroxyl group.

查看原文本刊更多论文

核桃酮的直接芳基化使WS-5995类似物的不同访问成为可能。

木酮的直接芳基化使WS-5995A和相关的天然产物WS-5995C能够简洁地访问，从而为WS-5995家族提供了一个入口。该方法可通过C-2或C-3芳基化获得内酰胺类似物，从而使酚羟基位置发生变化。细胞毒性研究揭示了酚羟基定位对生物活性的显著影响，其中c -3衍生的内酰胺显示出增强的效力。WS-5995A进一步去甲基化可增加活性，提示游离酚羟基的重要作用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Chemical & pharmaceutical bulletin 医学-化学综合

CiteScore

3.20

自引率

5.90%

发文量

132

审稿时长

1.7 months

期刊介绍： The CPB covers various chemical topics in the pharmaceutical and health sciences fields dealing with biologically active compounds, natural products, and medicines, while BPB deals with a wide range of biological topics in the pharmaceutical and health sciences fields including scientific research from basic to clinical studies. For details of their respective scopes, please refer to the submission topic categories below. Topics: Organic chemistry In silico science Inorganic chemistry Pharmacognosy Health statistics Forensic science Biochemistry Pharmacology Pharmaceutical care and science Medicinal chemistry Analytical chemistry Physical pharmacy Natural product chemistry Toxicology Environmental science Molecular and cellular biology Biopharmacy and pharmacokinetics Pharmaceutical education Chemical biology Physical chemistry Pharmaceutical engineering Epidemiology Hygiene Regulatory science Immunology and microbiology Clinical pharmacy Miscellaneous.