Synthesis and Characterization of Thiophene-derived Amido Bis-nitrogen Mustard and Its Antimicrobial and Anticancer Activities

Authors

  • Yidan Tang,

    1. Laboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China
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  • Jingqing Zhang,

    1. Chongqing Key Laboratory of Biochemical & Molecular Pharmacology, Medicine Engineering Research Center, Chongqing Medical University, Chongqing 400016, China
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  • Shaolin Zhang,

    1. Laboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China
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  • Rongxia Geng,

    Corresponding author
    1. Laboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China
    • Laboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China, Tel.: 0086-023-68254967; Fax: 0086-023-68254967
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  • Chenghe Zhou

    Corresponding author
    1. Laboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China
    • Laboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China, Tel.: 0086-023-68254967; Fax: 0086-023-68254967
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Abstract

The thiophene-derived amido bis-nitrogen mustard N2,N2,N5,N5-tetrakis(2-chloroethyl)-3,4-dimethylthiophene-2,5-dicarboxamide was designed and synthesized via five-step reactions from commercially available 2-chloroacetonitrile. This target compound was confirmed by 1H NMR, 13C NMR, MS, IR spectra and elemental analyses, and its structure was further characterized by X-ray single-crystal analysis. The biological activities for the title compound and some intermediates were evaluated in vitro for their antibacterial, antifungal and cytotoxic activities. The preliminary results showed that the title compound could inhibit efficiently the growth of the tested microorganisms including drug-resistant bacteria MRSA to some extent. Moreover, the target compound was found to be effective against prostatic carcinoma cell line (PC-3), breast carcinoma cell line (MCF-7), colon carcinoma (LoVo) and lung cancer (A549). Especially, it gave selective antitumor efficacy against prostatic carcinoma cell line (PC-3) at a low dose.

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