Advanced Search
CHEN Shumin, HUANG Wenlong, HU Guoqiang. Synthesis and antitumor activity of fluoroquinolone C-3 isostere V: ciprofloxacin acylhydrazone derivatives[J]. Journal of China Pharmaceutical University, 2014, 45(2): 161-164. DOI: 10.11665/j.issn.1000-5048.20140205
Citation: CHEN Shumin, HUANG Wenlong, HU Guoqiang. Synthesis and antitumor activity of fluoroquinolone C-3 isostere V: ciprofloxacin acylhydrazone derivatives[J]. Journal of China Pharmaceutical University, 2014, 45(2): 161-164. DOI: 10.11665/j.issn.1000-5048.20140205
shu

Synthesis and antitumor activity of fluoroquinolone C-3 isostere V: ciprofloxacin acylhydrazone derivatives

More Information
    Graphical Abstract
    • Abstract
  • To explore an efficient strategy for the transformation of antibacterial fluoroquinoles into antitumor fluoroquinolones and their structure-activity relationship, an acylhydrazone as bioisostere of the C-3 carboxylic group, twelve novel fluoroquinolone C-3 acylhydrazones 3a - 3l were synthesized from ciprofloxacin, respectively. The structures were characterized by element analysis and spectral data. The in vitro antitumor activity against SMMC- 7721, L1210 and HL60 cell lines exhibited more significantly inhibitory activity than the parent, in which compounds with electron-withdrawing group were comparable to doxorubicin. SAR showed that compounds with electron-withdrawing group had more potency than those with electron-donating group, after reduction of acylhydrazone moiety, antitumor activity disappeared. Thus, it is necessary for an acylhydrazone as a bioisostere of the C-3 carboxylic group to develop antitumor fluoroquinolone lead compounds.
    • FullText(HTML)
    • References (8)
  • [1]
    Dong,KC,Berger JM.Structural basis for gate-DNA recognition and bending by type IIA topoisomerases[J].Nature,2007,450(7 173):1 201-1 205.
    [2]
    Al-Trawneh SA,Zahra JA,Kamal MR,et al.Synthesis and biological evaluation of tetracyclic fluoroquinolones as antibacterial and anticancer agents[J].Bioorg Med Chem,2010,18(16):5 873-5 884.
    [3]
    Xu QJ,Hou LL,Wu ZF,et al.Synthesis and antitumor activity of fluoroquinolone C-3 isostere III:s-triazole oxadiazole methylsulfide derivatives from pefloxacin[J].J China Pharm Univ(中国药科大学学报),2013,44(6):511-514.
    [4]
    Hu GQ, Zhang ZQ, Wang HY, et al. Synthesis and antitumor activity of fluoroquinolon -3-yl fused heterocyclic systems(III):s-triazolothiadiazinone derivatives derived enrofoxacin[J].Acta Chim Sinica(化学学报),2009,67(22):2 592-2 596.
    [5]
    Guo ZR,Zhao HY.Challenges and strategies of drug innovation[J].Acta Pharm Sin(药学学报),2013,48(7):1 031-1 040.
    [6]
    Zhang B,Zhao Y,Zhai X,et al.Design,synthesis and anticancer activities of diaryl urea derivatives bearing N-acylhydrazone moiety[J].Chem Pharm Bull(Tokyo),2012,60(8):1 046-1 054.
    [7]
    Xu QJ,Hou LL,Wu XK,et al.Synthesis and antitumor activity of ciprofloxacin bis-(C3/C7 hydrazone)s[J].J China Pharm Univ(中国药科大学学报),2013,44(1):35-38.
    [8]
    Xie SQ,Chen YS,Wang GQ,et al.Part IV.Synthesis and antitumor evaluation of s-triazolothiadiazines and pyrazolo s-triazoles derived from ciprofloxacin[J].Acta Pharm Sin(药学学报),2012,47(1):66-71.
    • Related Articles

  • Related Articles

    [1]JI Shunli, SONG Fanfan, ZHENG Yang, DING Li. Simultaneous determination of amoxicillin and clavulanic acid by LC-MS/MS in human plasma and its application to a bioequivalence study[J]. Journal of China Pharmaceutical University, 2019, 50(6): 699-706. DOI: 10.11665/j.issn.1000-5048.20190610
    [2]XIAO Yuan-yuan, MA Peng-cheng, WANG Yan, REN Xin-yi, LIU Xiao-quan. Determination of 8′-hydroxy-dihydroergocryptine in human plasma by LC-MS/MS and its application to a bioequivalence evaluation[J]. Journal of China Pharmaceutical University, 2012, 43(2): 177-181.
    [3]Relative Bioavailability of Oxcarbazepine Tablets in Healthy Volunteers[J]. Journal of China Pharmaceutical University, 2004, (3): 50-53.
    [4]Bioequivalence Study of the Two Kinds of Ofloxacin Tablets in Healthy Volunteers[J]. Journal of China Pharmaceutical University, 1998, (6): 433-436.
    [5]Bioequivalence of Doxofylline in Healthy Volunteers[J]. Journal of China Pharmaceutical University, 1998, (5): 33-35.
    [6]Pharmacokinetics and Bioequivalence of Sparfloxacin in Healthy Subject[J]. Journal of China Pharmaceutical University, 1998, (3): 75-77.
    [7]Studies on Ibuprofen Suspension and Its Bioequivalence in Healthy Volunteers[J]. Journal of China Pharmaceutical University, 1997, (3): 11-16.
    [8]Assessment on Relative Bioavailability and Bioequivalence of Glipizide[J]. Journal of China Pharmaceutical University, 1995, (5): 311-313.
    [9]Relative Bioavailability and Bioequivalence Assessment of Domestic Amiloride Tablet[J]. Journal of China Pharmaceutical University, 1994, (1): 9-11.
    [10]Studies on Pharmacokinetics and Bioeqivalence of Aspirin Sustained-Release Pellets[J]. Journal of China Pharmaceutical University, 1993, (6): 334-337.

Catalog

    Get Citation
    PDF
    XML
    Article views (1652) PDF downloads (1801) Cited by()
    Turn off MathJax
    Article Contents
    Abstract
    References
    Related Articles

    Copyright © Journal of China Pharmaceutical University苏ICP备12050101号-2

    Address：24 Tongjia Lane, Nanjing City, Jiangsu Province （210009）Tel: 025-83271566E-mail: xuebao@cpu.edu.cn

    Supported by: Beijing Renhe Information Technology Co., Ltd.  Baidu Analytics

    Total visits：454475

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return