Design, synthesis and biological evaluation of a novel series of 1,3,4-oxadiazole bearing N-methyl-4-(trifluoromethyl)phenyl pyrazole moiety as cytotoxic agents

被引:102
|
作者
Puthiyapurayil, Pushpan [1 ,2 ]
Poojary, Boja [1 ]
Chikkanna, Chandrashekhar [3 ]
Buridipad, Sunil Kumar [4 ]
机构
[1] Mangalore Univ, Dept Chem, Mangalagangothri 574199, Karnataka, India
[2] Syngene Int Ltd, Bangalore 560099, Karnataka, India
[3] SDM Coll, Dept Med Chem, Dk 574342, Karnataka, India
[4] NET Pharm Coll, Dept Pharm Coll, Raichur 584103, Karnataka, India
关键词
N-Methyl-4(trifluoromethyl)phenyl; Pyrazole; Cytotoxic activity; MTT assay; Doxorubicin; Nuclear overhauser effect; ANTITUMOR-ACTIVITY; IN-VITRO; DERIVATIVES; INHIBITORS; IDENTIFICATION; ANALOGS; ETHERS;
D O I
10.1016/j.ejmech.2012.03.056
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
On account of the reported anticancer activity of pyrazoles and oxadiazoles, we have designed and synthesized a novel combinatorial library of S-substituted-1,3,4-oxadiazole bearing N-methyl-4-(trifluoromethyl)phenyl pyrazole moiety and tested for in-vitro cytotoxic activity by MTT assay. Amongst the tested compounds, the compound 5e was the most promising anticancer agent with IC50 value of 15.54 mu M in MCF-7 cells, compared to Doxorubicin as standard drug. The newly synthesized compounds were characterized by NOE, IR, H-1 NMR, C-13 NMR and LC-MS analysis. (C) 2012 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:203 / 210
页数:8
相关论文
共 50 条
  • [1] Design, synthesis, and biological evaluation of novel fluorinated pyrazole encompassing pyridyl 1,3,4-oxadiazole motifs
    Desai, Nisheeth C.
    Kotadiya, Ghanshyam M.
    Trivedi, Amit R.
    Khedkar, Vijay M.
    Jha, Prakash C.
    MEDICINAL CHEMISTRY RESEARCH, 2016, 25 (11) : 2698 - 2717
  • [2] Synthesis and biological evaluation of novel fluconazole analogues bearing 1,3,4-oxadiazole moiety as potent antifungal agents
    Liao, Jun
    Yang, Fan
    Zhang, Lei
    Chai, Xiaoyun
    Zhao, Qingjie
    Yu, Shichong
    Zou, Yan
    Meng, Qingguo
    Wu, Qiuye
    ARCHIVES OF PHARMACAL RESEARCH, 2015, 38 (04) : 470 - 479
  • [3] Synthesis and in vitro antiproliferative evaluation of novel nonsymmetrical disulfides bearing 1,3,4-oxadiazole moiety
    Zhao, Ji-Jun
    Wang, Xue-Feng
    Li, Bao-Lin
    Zhang, Rui-Lian
    Li, Bo
    Liu, Yu-Ming
    Li, Cai-Wen
    Liu, Jin-Biao
    Chen, Bao-Quan
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (18) : 4414 - 4416
  • [4] Synthesis and biological activity of novel 1,3,4-oxadiazole derivatives containing a pyrazole moiety
    Wei Yu
    Zhi-Wen Zhai
    David E. Wedge
    Stephen O. Duke
    Hong-Ke Wu
    Jian-Quan Weng
    Cheng-Xia Tan
    Yong-Gang Zhang
    Xing-Hai Liu
    Research on Chemical Intermediates, 2019, 45 : 5989 - 6001
  • [5] Synthesis and biological activity of novel 1,3,4-oxadiazole derivatives containing a pyrazole moiety
    Yu, Wei
    Zhai, Zhi-Wen
    Wedge, David E.
    Duke, Stephen O.
    Wu, Hong-Ke
    Weng, Jian-Quan
    Tan, Cheng-Xia
    Zhang, Yong-Gang
    Liu, Xing-Hai
    RESEARCH ON CHEMICAL INTERMEDIATES, 2019, 45 (12) : 5989 - 6001
  • [6] Novel Trifluoromethyl Pyridine Derivatives Bearing a 1,3,4-Oxadiazole Moiety as Potential Insecticide
    Xu, Fangzhou
    Wang, Yanyan
    Luo, Dexia
    Yu, Gang
    Wu, Yikun
    Dai, Ali
    Zhao, Yonghui
    Wu, Jian
    CHEMISTRYSELECT, 2018, 3 (10): : 2795 - 2799
  • [7] Synthesis and Insecticidal Activities of Novel Pyrazole Amides Containing 1,3,4-Oxadiazole Moiety
    Shi, Yujun
    Ye, Linyu
    Zhong, Sulin
    Cao, Xiongfei
    Dai, Hong
    Hong, Yu
    Li, Chunjian
    Shi, Jian
    Wu, Jinming
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (07) : 1844 - 1849
  • [8] Synthesis and Biological Evaluation of Theophylline Methyl 1,3,4-Oxadiazole as Anticancer Agents
    Gopinatha, Vindya K.
    Ray, Ujjayinee
    Mantelingu, Kempegowda
    Raghavan, Sathees C.
    Rangappa, Kanchugarakoppal S.
    RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2020, 46 (05) : 837 - 844
  • [9] Synthesis and biological evaluation of newer analogues of 2,5-disubstituted 1,3,4-oxadiazole containing pyrazole moiety as antimicrobial agents
    Malladi, Shridhar
    Isloor, Arun M.
    Peethambar, S. K.
    Fun, Hoong Kun
    ARABIAN JOURNAL OF CHEMISTRY, 2014, 7 (06) : 1185 - 1191
  • [10] Design, synthesis, and biological evaluation of novel fluorinated pyrazole encompassing pyridyl 1,3,4-oxadiazole motifs
    Nisheeth C. Desai
    Ghanshyam M. Kotadiya
    Amit R. Trivedi
    Vijay M. Khedkar
    Prakash C. Jha
    Medicinal Chemistry Research, 2016, 25 : 2698 - 2717