Synthesis and Biological Activities of Some New 3,6-Disubstituted 1,2,4-Triazolo[3,4-b]1,3,4-thiadiazole Derivatives

• Published in: Bulletin of the Korean Chemical Society Vol. 33; no. 12; pp. 3943 - 3949
• Main Authors: Rafiq, Muhammad, Saleem, Muhammad, Hanif, Muhammad, Maqsood, Muhammad Rizwan, Rama, Nasim Hasan, Lee, Ki-Hwan, Seo, Sung-Yum
• Format: Journal Article
• Language: English
• Published: 대한화학회 20.12.2012
• Subjects: 화학
• ISSN: 0253-2964; 1229-5949
• DOI: 10.5012/bkcs.2012.33.12.3943

A series of aromatic hydrazides 3a-j were prepared by refluxing esters 2a-j with hydrazine hydrate in methanol, which were prepared by the esterification of 1a-j. Acetohydrazides 3a-j upon treatment with carbon disulfide and methanolic potassium hydroxide yielded potassium dithiocarbazate salts 4a-j, which on refluxing with hydrazine hydrate yielded substituted 4-amino-5-aryl-3H-1,2,4-triazole-3-thiones 5a-j. The target compounds 6a-j were synthesized by condensing furan-3-carboxylic acid in the presence of polyphosphoric acid under reflux. The structures of newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, elemental analysis and mass spectrometric studies. All the synthesized compounds were screened for their urease, acetylcholine esterase inhibition, antioxidant and alkaline phosphatase inhibition activity. Almost all of the compounds 6a-j showed good to excellent activities against urease and acetylcholine esterase more than the reference drugs. Compounds 6f and 6g were more potent scavenger of free radicals than the reference n-propyl gallate. Compound 6b and 6h showed excellent activities of alkaline phosphatase as compare to the reference KH2PO4. KCI Citation Count: 0