Semisynthesis of Nocarterphenyl A and Its Analogues.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2025-01-24 Epub Date: 2024-12-27 DOI:10.1021/acs.jnatprod.4c01198

Yong Wang, Yanchao Xu, Dan Wu, Dongyang Wang, Peng Fu, Weiming Zhu, Liping Wang

引用次数: 0

Abstract

p-Terphenyl compounds are known to possess a diverse range of biological activities, making the synthesis of novel p-terphenyl derivatives a significant research objective. In this study, we report the first synthesis of nocarterphenyl A (1), characterized by a thiazole-fused p-terphenyl framework. Furthermore, we synthesized 18 additional analogs, including the naturally occurring compound 5-methoxy-4,7-bis(4-methoxyphenyl)benzo[d]thiazol-6-ol (9), employing a similar synthetic approach. Notably, compounds 12, 13, 15-17, and 19 demonstrated potent inhibitory effects against protein tyrosine phosphatase 1B (PTP1B), exhibiting IC₅₀ values ranging from 2.2 to 7.9 μM, which are lower than that of oleanolic acid (13.2 μM). Additionally, compound 14 was found to inhibit α-glucosidase from human colorectal adenocarcinoma (Caco-2) cells with an IC₅₀ value of 10.4 μM, which is also lower than that of acarbose (11.2 μM).

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诺卡特苯A及其类似物的半合成。

众所周知，对terphenyl化合物具有多种生物活性，因此合成新的对terphenyl衍生物是一个重要的研究目标。在这项研究中，我们报道了第一次合成nocarterphenyl A(1)，其特征是一个噻唑-融合对terphenyl框架。此外，我们还合成了另外18个类似物，包括天然化合物5-甲氧基-4,7-双（4-甲氧基苯基）苯并[d]噻唑-6-醇(9)，采用类似的合成方法。其中化合物12、13、15 ~ 17和19对蛋白酪氨酸磷酸酶1B （PTP1B）具有较强的抑制作用，IC50值在2.2 ~ 7.9 μM之间，低于齐齐果酸的IC50值（13.2 μM）。此外，化合物14对人结直肠癌（Caco-2）细胞α-葡萄糖苷酶有抑制作用，IC50值为10.4 μM，也低于阿卡波糖（11.2 μM）。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.