Synthesis, spectral analysis, antibacterial, antifungal, antioxidant and hemolytic activity studies of some new 2,5-disubstituted-1,3,4-oxadiazoles

被引:27
|
作者
Dhonnar, Sunil L. [1 ]
More, Rahul A. [2 ]
Adole, Vishnu A. [3 ]
Jagdale, Bapu S. [1 ]
Sadgir, Nutan, V [1 ]
Chobe, Santosh S. [1 ]
机构
[1] SP Pune Univ, Dept Chem, Mahatma Gandhi Vidyamandirs Loknete Vyankatrao Hi, Nasik 422003, India
[2] Swami Ramanand Teerth Marathwada Univ, Dayanand Sci Coll, Dept Microbiol, Latur 413512, India
[3] SP Pune Univ, Mahatma Gandhi Vidyamandirs Arts Sci & Commerce C, Dept Chem, Manmad 423104, Nashik, India
关键词
1,3,4-oxadiazole; Antibacterial; Antifungal; Antioxidant; Cytotoxicity; SUBSTITUTED 1,3,4-OXADIAZOLE; ANTIMICROBIAL ACTIVITY; EFFICIENT SYNTHESIS; MONOAMINE-OXIDASE; OXIDATIVE STRESS; DERIVATIVES; CYTOTOXICITY; INHIBITORS;
D O I
10.1016/j.molstruc.2021.132216
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Series of 1,3,4-oxadiazole derivatives (5a-5g and 5h, 5i) were synthesized and characterized by FT-IR, H-1 NMR, C-13 NMR and HR-MS spectral analysis. All the target compounds were screened for their in vitro antibacterial activity against two Gram-negative bacterial strains namely Escherichia coli (MTCC 405) and Salmonella typhi (MTCC 3224) and two Gram-positive bacterial strains namely Bacillus subtilis (MTCC 1790) and Bacillus megaterium (MTCC 1684) and antifungal activity against Aspergillus niger (MTCC 282), Rhizopus oryzae (MTCC 262), Penicillium chrysogenum (MTCC 974), and Candida albicans (MTCC 183) fungal strains. The synthesized compounds exhibited significant antibacterial and antifungal potential. Three compounds (5e, 5f and 5g) have shown higher antibacterial activity with very low MIC values comparable to streptomycin. According to the SAR study, the antibacterial efficacy can be intensified by substituting fluoro and methyl substituents at the para position in acid hydrazide. The synthesized compounds were also screened for % radical scavenging activity by OH and DPPH assay and found to be good antioxidant agents. Besides, the hemolytic study revealed that the synthesized 1,3,4-oxadiazoles possessed negligible cytotoxicity compared with the standard. (c) 2021 Elsevier B.V. All rights reserved.
引用
收藏
页数:8
相关论文
共 50 条
  • [31] Synthesis and antibacterial activity of some new 2,5-disubstituted-1,3,4-oxadiazole derivatives
    Somani, Rakesh R.
    Shirodkar, Prabhakar Y.
    Kadam, Vilasrao J.
    CHINESE JOURNAL OF CHEMISTRY, 2008, 26 (09) : 1727 - 1731
  • [32] Synthesis and biological activity of some 2,5-disubstituted 1,3,4-oxadiazoles
    Alam, O
    Gupta, SK
    Imran, M
    Khan, SA
    ASIAN JOURNAL OF CHEMISTRY, 2005, 17 (02) : 1281 - 1286
  • [33] Synthesis and in vitro antiproliferative activity of 2,5-disubstituted-1,3,4-oxadiazoles containing trifluoromethyl benzenesulfonamide moiety
    Kumar, Basavapatna N. Prasanna
    Mohana, Kikkeri N.
    Mallesha, Lingappa
    Veeresh, Bantal
    MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (07) : 3363 - 3373
  • [34] Synthesis and in vitro antiproliferative activity of 2,5-disubstituted-1,3,4-oxadiazoles containing trifluoromethyl benzenesulfonamide moiety
    Basavapatna N. Prasanna Kumar
    Kikkeri N. Mohana
    Lingappa Mallesha
    Bantal Veeresh
    Medicinal Chemistry Research, 2014, 23 : 3363 - 3373
  • [35] Synthesis and antimicrobial activity of some 2,5-disubstituted 1,3,4-oxadiazoles
    Honnalli, SS
    Ronad, PM
    Vijaybhasker, K
    Hukkeri, VI
    Kumar, R
    HETEROCYCLIC COMMUNICATIONS, 2005, 11 (06) : 505 - 508
  • [36] Design, Synthesis, Anticancer Activity and Molecular Docking Studies of 2,5-Disubstituted-1,3,4-Oxadiazoles Containing Benzirnidazole Moiety
    Katikireddy, Ramamurthy
    Kakkerla, Ramu
    Krishna, M. P. S. Murali
    Durgaiah, Gandamalla
    Reddy, Y. N.
    LETTERS IN ORGANIC CHEMISTRY, 2020, 17 (12) : 959 - 968
  • [37] SYNTHESIS OF SCHIFF-BASES, 2,5-DISUBSTITUTED-1,3,4-OXADIAZOLES AND 2,3-DISUBSTITUTED-4-THIAZOLIDINONES AS ANTIFUNGAL AGENTS
    SRIVASTAVA, SK
    PATHAK, RB
    BAHEL, SC
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1991, 68 (02) : 113 - 114
  • [38] Synthesis and antifungal activity of some new 1,3,4-oxadiazoles
    Bakht, MA
    Islam, M
    Siddiqui, AA
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 15 (03) : 297 - 298
  • [39] Synthesis, characterization and in vivo antitumor effect of new α,β-unsaturated-2,5-disubstituted-1,3,4-oxadiazoles
    Fray, M.
    ELBini-Dhouib, I
    Hamzi, I
    Doghri, R.
    Srairi-Abid, N.
    Lesur, D.
    Benazza, M.
    Abidi, R.
    Barhoumi-Slimi, T.
    SYNTHETIC COMMUNICATIONS, 2022, 52 (06) : 849 - 860
  • [40] SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF NEW 2,5-DISUBSTITUTED 1,3,4-OXADIAZOLES
    Rajak, Harish
    Gupta, Arun Kumar
    Kharya, Murli Dhar
    Mishra, Pradeep
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 19 (01) : 25 - 28