Synthesis and biological evaluation of novel substituted 1,3,4-thiadiazole and 2,6-di aryl substituted imidazo [2,1-b] [1,3,4] thiadiazole derivatives

被引:59
|
作者
Chandrakantha, B. [1 ]
Isloor, Arun M. [2 ]
Shetty, Prakash [3 ]
Fun, Hoong Kun [4 ]
Hegde, Gurumurthy [5 ]
机构
[1] Manipal Univ, Dept Chem, Manipal Inst Technol, Manipal 576104, Karnataka, India
[2] Natl Inst Technol Karnataka, Med Chem Lab, Dept Chem, Mangalore 575025, Karnataka, India
[3] Manipal Univ, Manipal Inst Technol, Dept Printing & Media Engn, Manipal 576104, Karnataka, India
[4] King Saud Univ, Coll Pharm, Dept Pharmaceut Chem, Riyadh 11451, Saudi Arabia
[5] Univ Malaysia Pahang, Fac Ind Sci & Technol, Kuantan 26300, Pahang Darul Ma, Malaysia
关键词
1,3,4-Thiadiazole; 2,6-Diaryl imidazo [2,1-b] [1,3,4] thiadiazole; Antibacterial; Antifungal activity; ANTIBACTERIAL ACTIVITY; ANTIVIRAL ACTIVITY; IN-VITRO; ANTITUMOR;
D O I
10.1016/j.ejmech.2013.10.056
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A new series of N-[5-(4-(alkyl/aryl)-3-nitro-phenyl)-[1,3,4-thiadiazol-2-yl]-2,2-dimethyl-propionamide 4 (a-1) and 6-(4-Methoxy-phenyl)-2-(4-alkyl/aryl)-3-nitro-phenyl)-Imidazo [2,1-b] [1,3,4] thiadiazole 6 (a-1) were synthesized starting from 5-(4-Fluoro-3-nitro-phenyl)-[1,3,4] thiadiazole-2-ylamine. The synthesized compounds were characterized by IR, NMR, mass spectral and elemental analysis. All the compounds were tested for antibacterial and antifungal activities. The antimicrobial activities of the compounds were assessed by well plate method (zone of inhibition). Compounds 4a, 4c and 6e, 6g displayed appreciable activity at the concentration 0.5-1.0 mg/mL. (C) 2013 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:316 / 323
页数:8
相关论文
共 50 条
  • [31] Intramolecular amidation:: synthesis of novel imidazo[2,1-b][1,3,4]thiadiazole and imidazo[2,1-b][1,3]thiazole fused diazepinones
    Kolavi, G
    Hegde, V
    Khazi, IA
    TETRAHEDRON LETTERS, 2006, 47 (16) : 2811 - 2814
  • [32] Synthesis and Antimicrobial Activity Evaluation of Pyridine Derivatives Containing Imidazo[2,1-b][1,3,4]Thiadiazole Moiety
    Yang, Liu
    Jiao, Yu-Xin
    Quan, Yan-Hua
    Li, Ming-Yu
    Huang, Xin-Yi
    Jin, Jun-Zheng
    Li, Siqi
    Quan, Ji-Shan
    Jin, Cheng-Hua
    CHEMISTRY & BIODIVERSITY, 2024, 21 (04)
  • [33] Novel Substituted Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives: Synthesis, Characterization, Molecular Docking Study, and Investigation of Their In Vitro Antifungal Activities
    Er, Mustafa
    Tahtaci, Hakan
    Karakurt, Tuncay
    Onaran, Abdurrahman
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (09) : 2555 - 2570
  • [34] Synthesis and antimicrobial studies of novel methylene bridged benzisoxazolyl imidazo[2,1-b][1,3,4]thiadiazole derivatives
    Lamani, Ravi S.
    Shetty, Nitinkumar S.
    Kamble, Ravindra R.
    Khazi, Imtiyaz Ahmed M.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (07) : 2828 - 2833
  • [35] Synthesis and Evaluation of Imidazole Derivatives Bearing Imidazo[2,1-b] [1,3,4]thiadiazole Moiety as Antibacterial Agents
    Xu, Wen-Bo
    Li, Siqi
    Zheng, Chang-Ji
    Yang, Yu-Xuan
    Zhang, Changhao
    Jin, Cheng-Hua
    MEDICINAL CHEMISTRY, 2024, 20 (01) : 40 - 51
  • [36] Synthesis and antimicrobial activity evaluation of pyrazole derivatives containing the imidazo[2,1-b][1,3,4]thiadiazole moiety
    Qi, Jun-Da
    Meng, Yu-Qing
    Sun, Jingxin
    Li, Wan-Xin
    Zhai, Hou-Xiang
    Zhang, Changhao
    Quan, Jishan
    Jin, Cheng-Hua
    ARCHIV DER PHARMAZIE, 2023, 356 (08)
  • [37] Synthesis and anti-tubercular activity of a series of 2-sulfonamido/trifluoromethyl-6-substituted imidazo[2,1-b]-1,3,4-thiadiazole derivatives
    Gadad, AK
    Noolvi, MN
    Karpoormath, RV
    BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (21) : 5651 - 5659
  • [38] Synthesis and Cdc25B Inhibition Activity of Novel Imidazo[2,1-b][1,3,4]thiadiazole Derivatives
    Li, Yingjun
    Luo, Tongchuan
    Jin, Kun
    Gao, Lixin
    Shao, Xin
    Sheng, Li
    Yu, Yang
    Li, Jia
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (02) : 325 - 333
  • [39] 2,6-Disubstituted imidazo[2,1-b][1,3,4]thiadiazole derivatives as potent staphylococcal biofilm inhibitors
    Cascioferro, Stella
    Parrino, Barbara
    Petri, Giovanna Li
    Cusimano, Maria Grazia
    Schillaci, Domenico
    Di Sarno, Veronica
    Musella, Simona
    Giovannetti, Elisa
    Cirrincione, Girolamo
    Diana, Patrizia
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 167 : 200 - 210
  • [40] Synthesis and Anticancer Activity of Thiadiazole Containing Thiourea, Benzothiazole and Imidazo[2,1-b][1,3,4]thiadiazole Scaffolds
    Avvaru, Stephen Paul
    Noolvi, Malleshappa N.
    More, Uttam A.
    Chakraborty, Sudipta
    Dash, Ashutosh
    Aminabhavi, Tejraj M.
    Narayan, Kumar P.
    Sutariya, Vishnu
    MEDICINAL CHEMISTRY, 2021, 17 (07) : 750 - 765