Synthesis of Thioloformate-Containing Lathyrane Diterpene Derivates via a [3,3] Sigmatropic Rearrangement and Their Anti-HIV Activity.

IF 3.3 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2025-03-25 DOI:10.1021/acs.jnatprod.5c00087

Lanfei Ji, Sihao Deng, Jin-Bu Xu, Xiaohuan Li, Steven De Jonghe, Dominique Schols, Feng Gao

引用次数: 0

Abstract

The [3,3] sigmatropic rearrangement of a lathyrane diterpene with various allylic thionoformates was carried out, affording C17-thioloformate-containing lathyrane derivatives (3a-3h) for the first time. The reaction features a mild, rapid, and easy operation. All newly synthesized derivatives were evaluated for potential antiviral activity against HIV-1 and HIV-2. The incorporation of an appropriate thionoformate into the lathyrane diterpene framework enhances their anti-HIV activity. The derivative 3d, featuring an O-(p-tolyl) carbonothionate substitution, exhibited the most potent anti-HIV activity, with an EC₅₀ value of 11.3 μM against HIV-1 NL 4.3 and an EC₅₀ value of 6.6 μM against HIV-2 ROD. Additionally, it demonstrated selectivity indices exceeding 4.0 and 6.8 against HIV-1 NL 4.3 and HIV-2 ROD, respectively.

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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.