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Synthesis of novel analogues on the α-carbon of houttuyfonate and SAR analysis of antibacterial activity with MOPAC

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Abstract

Three novel α-carbon derivatives of houttuyfonate—HOU-C8C1, HOU-C8C2, and HOU-C8C4—were designed and synthesized, and tested for their in vitro antibacterial activities against seven bacterial strains. A set of molecular properties of houttuyfonate and its five analogues were analyzed by MOPAC. Results indicated that the antibacterial activity of HOU-C8C1 is lower than that of HOU-C8. However, among HOU-C8C n (n = 1, 2, 4), as the hydrophobicity increased so did the activity, especially against Gram-positive bacteria. For the isomeric compounds HOU-C8C2 and HOU-C10, HOU-C8C4, and HOU-C12, the more negative the charges on carbon atom 2, the stronger the antibacterial activity exhibited. This suggests that the C(2) position is the antibacterial active center of houttuyfonate analogues, and that the weak antibacterial activities are possibly caused by the net negative charges on houttuyfonate homologues.

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Authors and Affiliations

  1. College of Pharmaceutical Sciences, Southwest University, No. 2, Tiansheng Road, Beibei, Chongqing, 400716, China

    Zhubo Li, Xiaoyan He & Hua Zuo

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  1. Zhubo Li
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  2. Xiaoyan He
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  3. Hua Zuo
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Correspondence to Zhubo Li.

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Li, Z., He, X. & Zuo, H. Synthesis of novel analogues on the α-carbon of houttuyfonate and SAR analysis of antibacterial activity with MOPAC. Med Chem Res 18, 362–372 (2009). https://doi.org/10.1007/s00044-008-9133-0

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  • DOI: https://doi.org/10.1007/s00044-008-9133-0

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