Synthesis and Characterization of Novel Series of 1,2,4-Triazolo[3,4-b]-1,3,4-Thiadiazole Derivatives of Anilinoacetic Acids as Promising Antioxidant Agents
Journal Title: Archives of Organic and Inorganic Chemical Sciences - Year 2018, Vol 2, Issue 2
Abstract
The preparation of a novel series of 6-arylaminomethyl-3-substituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles (5) by the cyclocondensation of 5-substituted-4-amino-3-mercapto-1,2,4-triazoles (2) with appropriately substituted anilinoacetic acids (4) employing phosphorous oxychloride is reported. The newly synthesized compounds (5) were screened for their antioxidant activity by DPPH radical scavenging assay and their structures were elucidated on the basis of their 1H-NMR, IR, Mass spectral and elemental analysis. Some of the tested compounds showed good DPPH radical scavenger activities comparable to that of standard BHA.The 1,2,4-triazole nucleus constitutes an integral component in drug discovery. It has been incorporated into both non-bridged drugs such as anastrozole (anticancer) [1,2], ribavirin (antiviral) [1,3], fluconazole, voriconazole (antifungal agents) [4] and in biologically active N-bridged drugs like triazolam (sedative agent) [1,5], estazolam and alprazolam (anxiolytic agents) [1,6,7]. The 1,3,4-thiadiazoles have attracted more interest to the researchers due to their prominent biological properties including anticonvulsant, anti-tubercular, anti-inflammatory, anti- leishmanial, antioxidant [8], antimicrobial and antidepressant activities [8,9]. There are also many drugs containing the 1,3,4-thiadiazole moiety such as acetazolamide, megazol and methazolamide [10]. Interestingly, some current reports showed that the fusion of the biolabile 1,2,4-triazole with 1,3,4-thiadiazole rings affords fused bicyclic compounds with improved biological activities than their corresponding non-bridged precursors. These include some ibuprofen-based 1,2,4-triazolo[3,4-b]-1,3,4- thiadiazoles with enhanced anti-inflammatory and analgesic properties than precursor ibuprofen [11-13], and some naproxen-based 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles with enhanced analgesic, ulcerogenic, anti-inflammatory, and lipid peroxidation activities than starting naproxen [14]. Furthermore, N-(heteroarylmethyl) aniline derivatives with varied potent activities such as antimicrobial [15,16], antifungal, anticancer [17,18], herbicidal [19] and analgesic [20] were also reported. Prompted by these observations and in continuation of our research for new bioactive fused heterocycles [21,22], we herein describe the synthesis of a new series of 6-arylaminomethyl-3- substituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles as promising antioxidant agents.
Authors and Affiliations
Jean Baptiste Nkurunziza, Balakrishna Kalluraya
Keywords
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- EP ID EP602971
- DOI 10.32474/AOICS.2018.02.000135
- Views 44
- Downloads 0
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