title: Synthesis, structural elucidation and bioevaluation of 4-amino-1,2,4-triazole-3-thione's Schiff base derivatives.
abstract: In this study, a series of ten triazole Schiff base derivatives 6a-j were synthesized through microwave assisted imine formation by reacting substituted amino triazole 5 with different substituted aldehydes. All the synthesized compounds were evaluated for their inhibitory activity against mushroom tyrosinase. Two of the compounds 6a and 6b among the series 6a-j were found to be highly potent tyrosinase inhibitors with IC50 values of 10.09 ± 1.03 and 6.23 ± 0.85 µM, respectively, which were even higher than that of the reference inhibitor kojic acid (IC50 = 16.6 ± 2.8 µM). Compounds 6e and 6f with IC50 values of 20.27 ± 2.78 and 26.02 ± 4.14 µM, respectively, were comparable to the reference inhibitor, and the remaining compounds had a moderate inhibitory activity against mushroom tyrosinase. The most potent compounds (6a, 6b) were used in the kinetic and optical analyses. The inhibition kinetics analyzed with Lineweaver-Burk plots revealed that both compounds 6a and 6b were non-competitive inhibitors of tyrosinase with inhibition constant values of 0.023 and 0.022 mM, respectively.
authors.affiliation: Department of Biology, Kongju National University, Gongju, Chungnam, 314-701, Republic of Korea.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Rafiq
authors.affiliation: Department of Chemistry, Kongju National University, Gongju, Chungnam, 314-701, Republic of Korea.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Saleem
authors.affiliation: Department of Chemistry, GC University Faisalabad (Sub Campus Layyah), Faisalabad, Pakistan.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Hanif
authors.affiliation: Department of Chemistry, Chungnam National University, Daejeon, 305-754, Republic of Korea.
authors.forename: Sung Kwon
authors.initials: SK
authors.lastname: Kang
authors.affiliation: Department of Biology, Kongju National University, Gongju, Chungnam, 314-701, Republic of Korea.
authors.forename: Sung-Yum
authors.initials: SY
authors.lastname: Seo
authors.affiliation: Department of Chemistry, Kongju National University, Gongju, Chungnam, 314-701, Republic of Korea. khlee@kongju.ac.kr.
authors.forename: Ki Hwan
authors.initials: KH
authors.lastname: Lee
mesh_terms: D000363:Agaricales / Q000201:enzymology*; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D007700:Kinetics; D008956:Models, Chemical; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D012545:Schiff Bases; D013329:Structure-Activity Relationship; D013871:Thiones / Q000138:chemical synthesis* / Q000494:pharmacology*; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D004791:Enzyme Inhibitors; D012545:Schiff Bases; D013871:Thiones; D014230:Triazoles; D014442:Monophenol Monooxygenase; C533754:4-amino-1,2,4-triazole
keywords: Inhibitors; Kinetic analysis; Non-competitive; Tyrosinase