Semisynthesis of Nocarterphenyl A and Its Analogues

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2024-12-27 DOI:10.1021/acs.jnatprod.4c0119810.1021/acs.jnatprod.4c01198

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

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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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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.