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Synthesis and Characterization of Thiophene‐derived Amido Bis‐nitrogen Mustard and Its Antimicrobial and Anticancer Activities
Author(s) -
Tang Yidan,
Zhang Jingqing,
Zhang Shaolin,
Geng Rongxia,
Zhou Chenghe
Publication year - 2012
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201100668
Subject(s) - chemistry , antimicrobial , thiophene , cell culture , nitrogen mustard , antifungal , in vitro , growth inhibition , bacteria , nitrogen , proton nmr , rhizosphere , microorganism , nuclear chemistry , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , microbiology and biotechnology , medicine , chemotherapy , genetics , biology , cyclophosphamide
The thiophene‐derived amido bis‐nitrogen mustard N 2 , N 2 , N 5 , N 5 ‐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 1 H NMR, 13 C 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.