Citation: Nagabhushana Nayak, Jurupula Ramprasad, Udayakumar Dalimba, Perumal Yogeeswari, Dharmarajan Sriram. Synthesis and antimycobacterial screening of new N-(4-(5-aryl-3-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrazol-1-yl)phenyl)-4-amide derivatives[J]. Chinese Chemical Letters, ;2016, 27(03): 365-369. doi: 10.1016/j.cclet.2016.01.015 shu

Synthesis and antimycobacterial screening of new N-(4-(5-aryl-3-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrazol-1-yl)phenyl)-4-amide derivatives

a.
a. Organic Chemistry Laboratory, Department of Chemistry, National Institute of Technology Karnataka, Surathkal, Srinivasanagar, Mangalore 575025, India;
b.
b. Medicinal Chemistry and Drug Discovery Research Laboratory, Pharmacy Group, Birla Institute of Technology and Science-Pilani, Hyderabad Campus, Jawahar Nagar 500078, Telangana, India

Corresponding author: Udayakumar Dalimba,
Received Date: 3 April 2015
Available Online: 29 July 2015

This article demonstrates the synthesis, characterization and the study of in vitro antitubercular activities of twenty four new N-(4-(5-aryl-3-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrazol-1-yl)phenyl)-4-amide derivatives (8a-x). The antitubercular activity of the compounds against Mycobacterium tuberculosis H₃₇Rv (MTB) revealed that 2-chloro-N-(4-(5-(4-chlorophenyl)-3-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrazol-1-yl)phenyl)benzamide (8n) is the most promising lead molecule with a MIC of 1.56 μg/mL, while the corresponding unsubstituted benzamide derivative (8o) is the next most active molecule with a MIC of 3.13 μg/mL. Interestingly, the pyrazole intermediate 5b containing chlorophenyl and N-acylcarbohydrazide substituents also showed significant activity (MIC=3.13 μg/mL). Further, the active molecules did not show toxicity against a normal NIH 3T3 cell line, signifying their suitability for further drug development.
- Pyrazole-oxadiazole hybrids,
- Antitubercular activity,
- SC-XRD analysis,
- In vitro cytotoxicity
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