Synthesis of new heterocyclic hybrids based on pyrazole and thiazolidinone scaffolds as potent inhibitors of tyrosinase |
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Authors: | Shrikant S Gawande Suchita C Warangkar Babasaheb P Bandgar Chandrahasya N Khobragade |
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Institution: | 1. Medicinal Chemistry Research Laboratory, School of Chemical Sciences, Bahirji Smarak Mahavidyalaya, Basmathnagar 431512, Hingoli Dist., Maharashtra, India;2. Biochemistry Research Laboratory, School of Life Sciences, S.R.T.M. University, Nanded 431606, Maharashtra, India;3. Medicinal Chemistry Research Laboratory, School of Chemical Sciences, Solapur University, Solapur 413255, Maharashtra, India |
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Abstract: | As a part of ongoing studies in developing new Tyrosinase inhibitors, a class of structurally novel 2-(2,4-dimethoxy phenylamino)-5 methylene-4-thiazolinone derivatives were synthesized by incorporating 2-(2,4-dimethoxy-phenylamino)-thiazol-4-one with various 1-(1-methyl-buta-1,3-dienyl)-3-phenyl-1H-pyrazole-4-carbaldehyde. The results showed that some of the synthesized compounds exhibited significant inhibitory activities. Especially, 5-3-(2-chloro-phenyl)-1-phenyl-1H-pyrazol-4-ylmethylene]-2-(2,4-dimethoxy-phenylamino)-thiazol-4-one (5h) and 5-3-(3-chloro-phenyl)-1-phenyl-1H-pyrazol-4-ylmethylene]-2-(2,4-dimethoxy-phenylamino)-thiazol-4-one (5g) possessing 2-chloro-phenyl and 3-chloro-phenyl group exhibited the most potent tyrosinase inhibitory activity with an IC50 value of 34.12 and 52.62 μM, respectively. The inhibition mechanism analysis of 5h and 5g thiazolidinone derivatives demonstrated that the inhibitory effects of the compounds on tyrosinase were reversible and competitive. Preliminary structure–activity relationships (SAR) analysis suggested that further development of such compounds might be of interest, as it manifests simple reversible slow binding inhibition against monophenolase and diphenolase. |
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