Synthesis, cytotoxic evaluation of novel 2-((1H-indol-3-yl) methyl)-5-alkyl-1,3,4-oxadiazole and 2-alkyl-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole derivatives

被引:0
|
作者
Vijayendar, Venepally [1 ,3 ]
Routhu, Sunitha Rani [2 ,3 ]
Kumar, C. Ganesh [2 ,3 ]
Jala, Ram Chandra Reddy [1 ,3 ]
机构
[1] CSIR Indian Inst Chem Technol, Ctr Lipid Res, Uppal Rd, Hyderabad 500007, India
[2] CSIR Indian Inst Chem Technol, Med Chem & Biotechnol Div, Uppal Rd, Hyderabad 500007, India
[3] Acad Sci & Innovat Res, New Delhi, India
关键词
Renewable materials; fatty acids; oxadiazoles; indolyl; cytotoxicity; SULFONE DERIVATIVES; COMBRETASTATIN A-4; ANTICANCER; ANALOGS; GROWTH; BINDING;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Interest in the biological applications of oleochemicals has resulted in the development of new heterocyclic compounds from the fatty acids which are renewable raw materials. In the present study the synthesis of hybrid compounds by involving fatty acids, indole-3-acetic acid (heteryl) and trimethoxy benzoic acid (aryl) to derive 2, 5-substituted 1,3,4-oxadiazole moiety using molecular hybridization approach has been carried out. A series of novel 2-((1H-indol-3-yl) methyl)-5-alkyl-1,3,4-oxadiazoles 4a-j and 2-alkyl-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole 8a-j analogues have been synthesized and evaluated for their cytotoxicity against A549, MCF-7 and HeLa cell lines. Almost all the tested compounds reveal cytotoxicity against all the cell lines, especially 2-((1H-indol-3-yl) methyl)-5-alkyl-1,3,4-oxadiazoles based compounds (4c, 4d, 4e) which display potent inhibitory activity with IC50 values ranging between 8.26 to 11.36 mu M.
引用
收藏
页码:465 / 473
页数:9
相关论文
共 50 条
  • [1] Synthesis and bioactivity of 2-substitued phenyl-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole derivatives
    Chen, Jiang
    Xu, Rui-Qing
    Song, Bao-An
    Jin, Lin-Hong
    Hu, De-Yu
    Yang, Song
    Zhang, Guo-Ping
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2006, 26 (10) : 1418 - 1423
  • [2] Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives
    Chen, Cai-Jun
    Song, Bao-An
    Yang, Song
    Xu, Guang-Fang
    Bhadury, Pinaki S.
    Jin, Lin-Hong
    Hu, De-Yu
    Li, Qian-Zhu
    Liu, Fang
    Xue, Wei
    Lu, Ping
    Chen, Zhuo
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (12) : 3981 - 3989
  • [3] Synthesis, Crystal Structure and Antibacterial Activity of 2-(p-Tolyl)-5-(3,4,5-trimethoxyphenyl)-1,3,4-oxadiazole
    Liu, Xianping
    He, Daohang
    [J]. ASIAN JOURNAL OF CHEMISTRY, 2014, 26 (11) : 3216 - 3218
  • [4] 2-(1-benzyl-5-methyl-1H-imidazol-4-yl)-1,3,4-oxadiazole
    Li, Jing
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O2976 - U2993
  • [5] 2-(1-benzyl-4-methyl-1H-imidazol-5-yl)1,3,4-oxadiazole
    Li, Jing
    Zhou, Hong-Bin
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O2977 - U3002
  • [6] 5-(3,4,5-Trimethoxyphenyl)-1,3,4-oxadiazole-2(3H)-thione
    Saeed, Aamer
    Akram, Muhammad
    Rauf, Abdul
    Bolte, Michael
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1911 - U280
  • [7] Synthesis and Properties of Novel 1,3,4-Oxadiazole Derivatives
    Zhang, Xiaobing
    Zhang, Zimin
    Zhang, Yugui
    Li, Min
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2009, 29 (02) : 297 - 301
  • [8] EFFICIENT SYNTHESIS OF 2, 5-DISUBSTITUTED 1,3,4-OXADIAZOLE DERIVATIVES
    Dhotre, Bharat K.
    Raut, Santosh, V
    Kohire, Ram B.
    Nagare, Dnyaneshwar
    Arif, Pathan Mohd
    [J]. HETEROCYCLIC LETTERS, 2020, 10 (04): : 667 - 674
  • [9] Synthesis of novel glycosyl 1,3,4-oxadiazole derivatives
    Liu, Weiwei
    Li, Quxiang
    Cheng, Fengchang
    Shi, Dahua
    Cao, Zhiling
    [J]. HETEROCYCLIC COMMUNICATIONS, 2014, 20 (06) : 333 - 338
  • [10] Synthesis and characterization of 1,3,4-thiadiazole and 1,3,4-oxadiazole derivatives containing 2-chloropyridin-5-yl-methyl moiety
    Holla, BS
    Prasanna, CS
    Poojary, B
    Rao, KS
    Shridhara, K
    Bhat, UG
    [J]. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2004, 43 (10): : 2170 - 2174