Synthesis, antioxidant activities and urease inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives

• Published in: European journal of medicinal chemistry Vol. 45; no. 11; pp. 5200 - 5207
• Main Authors: Khan, Imtiaz, Ali, Sajid, Hameed, Shahid, Rama, Nasim Hasan, Hussain, Muhammad Tahir, Wadood, Abdul, Uddin, Reaz, Ul-Haq, Zaheer, Khan, Ajmal, Ali, Sajjad, Choudhary, M. Iqbal
• Format: Journal Article
• Language: English
• Published: ISSY-LES-MOULINEAUX Elsevier Masson SAS 01.11.2010; Elsevier
• Subjects: 1,2,4-Triazoles; 1,3,4-Thiadiazoles; Analytical, structural and metabolic biochemistry; Antioxidant activities; Antioxidants - chemical synthesis; Antioxidants - pharmacology; Biological and medical sciences; Chemistry, Medicinal; Enzymes and enzyme inhibitors; Fundamental and applied biological sciences. Psychology; Hydrolases; Inhibitory Concentration 50; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Pharmacology & Pharmacy; Science & Technology; Spectrometry, Mass, Electrospray Ionization; Thiadiazoles - chemical synthesis; Thiadiazoles - pharmacology; Triazoles - chemical synthesis; Triazoles - pharmacology; Urease - antagonists & inhibitors; Urease inhibition; Urease inhibition; Antioxidant activities; 1,3,4-Thiadiazoles; 1,2,4-Triazoles; POTATO; Nitro compound; Sulfur nitrogen heterocycle; Five membered ring; DPPH; Enzyme; Nitrogen heterocycle; Benzene derivatives; Enzyme inhibitor; Urease; Antioxidant; In vitro; Radical scavenger; Structure activity relation; Chlorine Organic compounds; Hydrolases; Superoxide radicals; Chemical synthesis
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2010.08.034

New series of 4,5-disubstituted-2,4-dihydro-3 H-1,2,4-triazole-3-thiones (8a– j) and 2,5-disubstituted-1,3,4-thiadiazoles (9a– h) were synthesized by dehydrative cyclization of hydrazinecarbothioamide derivatives (7a– k) by refluxing in 4 N aqueous sodium hydroxide and by overnight stirring with polyphosphoric acid, respectively. The structures of the newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, elemental analysis and mass spectroscopic studies and the synthesized compounds were screened for their antioxidant and urease inhibition activities. N-(2,4-Dimethylphenyl)-5-(4-nitrophenyl)-1,3,4-thiadiazol-2-amine (9h) showed excellent antioxidant activity more than the standard drug whereas 4-(2,4-dimethylphenyl)-5-(3-nitrophenyl)-2,4-dihydro-3 H-1,2,4-triazole-3-thione (8d) and 4-(2,3-dimethylphenyl)-5-phenyl-2,4-dihydro-3 H-1,2,4-triazole-3-thione (8e) exhibited potent urease inhibitory activities. A new series of 4,5-disubstituted-2,4-dihydro-3 H-1,2,4-triazole-3-thiones and 2,5-disubstituted-1,3,4-thiadiazoles has been reported. The synthesized compounds were evaluated for their antioxidant and urease inhibition activities. [Display omitted]