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CHEN Shumin, HUANG Wenlong, HU Guoqiang. Synthesis and antitumor activities of fluoroquinolone C-3 isosteres(VI):s-triazole-acylhydrazone methylsulfide derivatives[J]. Journal of China Pharmaceutical University, 2014, 45(5): 511-516. DOI: 10.11665/j.issn.1000-5048.20140501
Citation: CHEN Shumin, HUANG Wenlong, HU Guoqiang. Synthesis and antitumor activities of fluoroquinolone C-3 isosteres(VI):s-triazole-acylhydrazone methylsulfide derivatives[J]. Journal of China Pharmaceutical University, 2014, 45(5): 511-516. DOI: 10.11665/j.issn.1000-5048.20140501
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Synthesis and antitumor activities of fluoroquinolone C-3 isosteres(VI):s-triazole-acylhydrazone methylsulfide derivatives

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  • To discover an efficient optimization method for modification of the fluoroquinolone C-3 carboxylic group, the title fluoroquinolon-3-yl s-triazole-acylhydrazone methylsulfide derivatives( 6a - 6q )were designed and synthesized from pefloxacin on the basis of pharmacophore combination principle with a functionalized acylhydrazone group as a modified side-chain for the C-3 bioisosteric s-triazole of pefloxacin. The structures were characte-rized by element analysis and spectral data, and the in vitro antitumor activity against SMMC-7721, L1210 and HL60 cell lines was evaluated by MTT assay. The results showed that the title compounds exhibited more significant inhibitory activity than that of the parent pefloxacin, in which compounds with electron-withdrawing group attached on aryl ring had more potency than that of compounds with electron-donating group, especially compounds with carboxylic substituent were comparable to control doxorubicin. It suggests that carboxylic residue around the C-3 bioisostere is favorable to improve the antitumor activity.
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    • References (9)
  • [1]
    Chou LC,Tsai MT,Hsu MH,et al.Design,synthesis,and precli-nical evaluation of new 5,6-(or 6,7-)disubstituted-2-(fluorophenyl)quinolin-4-one derivatives as potent antitumor agents[J].J Med Chem,2010,53(22):8 047-8 058.
    [2]
    Chang YH,Hsu MH,Wang SH,et al.Design and synthesis of 2-(3-benzo[b]thienyl)-6,7-methylenedioxyquinolin-4-one analogues as potent antitumor agents that inhibit tubulin assembly[J].J Med Chem,2009,52(15):4 883-4 891.
    [3]
    Tsuzuki Y,Tomita K,Shibamori K,et al.Synthesis and structure-activity relationships of novel 7-substituted 1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acids as antitumor agents.Part 2[J].J Med Chem,2004,47(8):2 097-2 109.
    [4]
    Cheng YY,Liu CY,Tsai MT,et al.Design,synthesis,and mechanism of action of 2-(3-hydroxy-5-methoxyphenyl)-6-pyrrolidinylquinolin-4-one as a potent anticancer lead[J].Bioorg Med Chem Lett,2013,23(18):5 223-5 227.
    [5]
    Azéma J, Guidetti B, Korolyov A, et al. Synthesis of lipophilic dimeric C-7/C-7-linked ciprofloxacin and C-6/C-6-linked levofloxacin derivatives.Versatile in vitro biological evaluations of monomeric and dimeric fluoroquinolone derivatives as potential antitumor,antibacterial or antimycobacterial agents[J].Eur J Med Chem,2011,46(12):6 025-6 038.
    [6]
    Zhou Y,Xu,Sun Y,et al.Synthesis,cytotoxicity and topoisome-rase II inhibitory activity of lomefloxacin derivatives[J].Bioorg Med Chem Lett,2013,23(10):2 974-2 978.
    [7]
    Chen SM,Huang WL,Hu GQ.Synthesis and antitumor activity of fluoroquinolone C-3 isostere V:ciprofloxacin acylhydrazone deri-vatives[J].J China Pharm Univ(中国药科大学学报),2014,45(2):161-164.
    [8]
    Sun YS,Xu QJ,Hou LL,et al.Synthesis antitumor activity of fluoroquinolone C-3 bioisosteres(IV):s-triazole-oxadiazole methylsulfide Mannich-base derivatives[J].J China Pharm Univ(中国药科大学学报),2014,45(1):39-42.
    [9]
    Xie SQ,Chen YS,Wang GQ,et al.Part IV.Synthesis and antitumor evaluation of s-triazolothiadiazine and pyrazolo-s-triazoles from ciprofloxacin[J].Acta Pharm Sin(药学杂志),2012,47(1):66-71.
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