Synthesis of Analogues of Flazin, in Particular, Flazinamide, as Promising Anti-HIV Agents

Authors

  • Jian-Guo Tang,

    1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, P. R. China, (phone: +86-871-5216327; fax: +86-871-5150227)
    2. Graduate School of the Chinese Academy of Sciences, Beijing 100039, P. R. China
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  • Yun-Hua Wang,

    1. Laboratory of Molecular Immunopharmacology, Key Laboratory of Animal Models and Human Disease Mechanisms, Kunming Institute of Zoology, Chinese Academy of Sciences, Kunming 650223, P. R. China
    2. Graduate School of the Chinese Academy of Sciences, Beijing 100039, P. R. China
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  • Rui-Rui Wang,

    1. Laboratory of Molecular Immunopharmacology, Key Laboratory of Animal Models and Human Disease Mechanisms, Kunming Institute of Zoology, Chinese Academy of Sciences, Kunming 650223, P. R. China
    2. Graduate School of the Chinese Academy of Sciences, Beijing 100039, P. R. China
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  • Ze-Jun Dong,

    1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, P. R. China, (phone: +86-871-5216327; fax: +86-871-5150227)
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  • Liu-Meng Yang,

    1. Laboratory of Molecular Immunopharmacology, Key Laboratory of Animal Models and Human Disease Mechanisms, Kunming Institute of Zoology, Chinese Academy of Sciences, Kunming 650223, P. R. China
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  • Yong-Tang Zheng,

    1. Laboratory of Molecular Immunopharmacology, Key Laboratory of Animal Models and Human Disease Mechanisms, Kunming Institute of Zoology, Chinese Academy of Sciences, Kunming 650223, P. R. China
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  • Ji-Kai Liu

    1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, P. R. China, (phone: +86-871-5216327; fax: +86-871-5150227)
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Abstract

Flazin isolated from the fruiting bodies of Suillus granulatus was found to possess weak anti-HIV activity (EC50=2.36 μM, TI=12.1). To establish a SAR study, 46 flazin analogues were synthesized, and their anti-HIV activities were evaluated in vitro. Among them, flazinamide (9a) showed the most potent activity with an EC50 value of 0.38 μM and a TI value of 312.0. The results suggested that appropriate substituents at positions 3, 1′, and 5′ of flazin might play a crucial role in determining their anti-HIV activities, and that flazinamide can be considered as a promising, readily available anti-HIV agent.

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