Novel 1,2,4-triazole analogues as mushroom tyrosinase inhibitors: synthesis, kinetic mechanism, cytotoxicity and computational studies

Vanjare, Balasaheb D.; Mahajan, Prasad G.; Dige, Nilam C.; Raza, Hussain; Hassan, Mubashir; Han, Yohan; Kim, Song Ja; Seo, Sung‐Yum; Lee, Ki Hwan

doi:10.1007/s11030-020-10102-5

Cited by 23 publications

(17 citation statements)

References 62 publications

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“…The search for biologically active substances among 1,2,4-triazole derivatives and the creation of a drug based on them is a promising area of research [1][2][3][4][5]. Synthesis of 1,2,4-triazoles fused to another heterocyclic ring has attracted wide spread attention due to their diverse applications as antibacterial [6],…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Properties and Biological Potential Some Condensed Derivatives 1,2,4-Triazole

Gotsulya

Brytanova

2022

Ankara Universitesi Eczacilik Fakultesi Dergisi

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Objective:The aim of the work was to develop effective methods for the synthesis of biologically active heterocyclic systems containing pyrrole, indole and 1,2,4-triazole. In this study, firstly fourteen [1,2,4]triazolo [3,4-b][1,3,4]thiadiazoles compounds requiring for this study were synthesized.Material and Method: Chemical structures of synthesized compounds were characterized with elemental analysis, 1 H NMR, LC-MS techniques. The biological potential of the synthesized substances was estimated by the molecular docking method.Result and Discussion: An optimal method for the synthesis of [1,2,4]triazolo [3,4-b][1,3,4]thiadiazoles has been developed. In molecular modeling studies, the compounds were found to be similar to known drugs in some respects. Besides, the interaction of each molecule in the active site of the crystal structures of cyclooxygenase-1, lanosterol 14-α-demethylase, kinases of anaplastic lymphoma were considered as in silico.

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Section: Introductionmentioning

confidence: 99%

“…The combination of 4-amino-1,2,4-triazole-3-thiol with pyrrole or indole allows to obtain 4amino-5-heteryl-1,2,4-triazole-3-thiols, which in the reactions of heterocyclization with aromatic carboxylic acids form [1,2,4]triazolo [3,4-b] [1,3,4]thiadiazoles.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Properties and Biological Potential Some Condensed Derivatives 1,2,4-Triazole

Gotsulya

Brytanova

2022

Ankara Universitesi Eczacilik Fakultesi Dergisi

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“…The synthesis route for the intermediates 2(a–c) , 3(a–c) , 5(a–c) , 6(a–c) , halogen-substituted/unsubstituted 2-chloro-N-phenyl acetamide derivatives 8(a–c) and for target 1,2,4-triazole analogues 9(a–i) are delineated in Scheme 1 . The compounds were synthesized by following our previously published method [ 17 , 18 ]. The target compound was synthesized by the coupling of 3-, 4-, and 5-substituted 1,2,4-triazole-3-thiol derivative 6(a–c) with different 2-chloro-N-phenyl acetamide derivatives 8(a–c) under the basic condition with a good yield.…”

Section: Resultsmentioning

confidence: 99%

Biological and Cheminformatics Studies of Newly Designed Triazole Based Derivatives as Potent Inhibitors against Mushroom Tyrosinase

et al. 2022

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A series of nine novel 1,2,4-triazole based compounds were synthesized through a multistep reaction pathway and their structures were scrutinized by using spectral methods such as FTIR, LC-MS, 1H NMR, and 13C NMR. The synthesized derivatives were screened for inhibitory activity against the mushroom tyrosinase and we found that all the synthesized compounds demonstrated decent inhibitory activity against tyrosinase. However, among the series of compounds, N-(4-fluorophenyl)-2-(5-(2-fluorophenyl)-4-(4-fluorophenyl)-4H-1,2,4-triazol-3-ylthio) acetamide exhibited more prominent activity when accompanied with the standard drug kojic acid. Furthermore, the molecular docking studies identified the interaction profile of all synthesized derivatives at the active site of tyrosinase. Based on these results, N-(4-fluorophenyl)-2-(5-(2-fluorophenyl)-4-(4-fluorophenyl)-4H-1,2,4-triazol-3-ylthio) acetamide could be used as a novel scaffold to design some new drugs against melanogenesis.

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“…For example, oxindole derivative A showed good TYR inhibitory activity (IC 50 =63.37 μM) compared to Kojic acid (IC 50 =22.52 μM). On the other hand, several series of N ‐phenylacetamide derivatives with high inhibitory activity against TYR have been reported [18,19] . In this regards, one of the most potent synthetic TYR inhibitor ever reported, is 1,3,4‐oxadiazole‐ N ‐phenylacetamide B (IC 50 =0.003 μM) that is 5600 fold more potent that Kojic acid (IC 50 =16.83±1.16 μM) [19] .…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, several series of N-phenylacetamide derivatives with high inhibitory activity against TYR have been reported. [18,19] In this regards, one of the most potent synthetic TYR inhibitor ever reported, is 1,3,4-oxadiazole-N-phenylacetamide B (IC 50 = 0.003 μM) that is 5600 fold more potent that Kojic acid (IC 50 = 16.83 � 1.16 μM). [19] Furthermore, several series of thiosemicarbazide derivatives as promising TYR inhibitor have been reported.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, in Vitro, and in Silico Evaluation of N‐Phenylacetamide‐Oxindole‐Thiosemicarbazide Hybrids as New Potential Tyrosinase Inhibitors

Boroujeni

Haghighijoo

Mohammadi‐Khanaposhtani

et al. 2022

Chemistry & Biodiversity

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A novel series of N‐phenylacetamide‐oxindole‐thiosemicarbazide hybrids were synthesized and evaluated for their tyrosinase inhibitory activity. According to tyrosinase inhibition results, all the synthesized compounds showed high tyrosinase inhibitory activity with IC50 values ranging from 0.8 to 3.88 μM in comparison to positive control kojic acid with IC50 value of 36.32 μM. Among tested compounds, analog 7o, containing the 2‐methyl‐4‐nitrophenyl on N‐phenylacetamide moiety displayed superior tyrosinase inhibition. This compound was around 45‐fold more potent than kojic acid. The kinetic analysis of compound 7o demonstrated that this compound is a competitive inhibitor against tyrosinase. Docking study of this compound demonstrated that compound 7o interacted with critical histidine residues within tyrosinase active site.

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Novel 1,2,4-triazole analogues as mushroom tyrosinase inhibitors: synthesis, kinetic mechanism, cytotoxicity and computational studies

Cited by 23 publications

References 62 publications

Synthesis, Properties and Biological Potential Some Condensed Derivatives 1,2,4-Triazole

Synthesis, Properties and Biological Potential Some Condensed Derivatives 1,2,4-Triazole

Biological and Cheminformatics Studies of Newly Designed Triazole Based Derivatives as Potent Inhibitors against Mushroom Tyrosinase

Design, Synthesis, in Vitro, and in Silico Evaluation of N‐Phenylacetamide‐Oxindole‐Thiosemicarbazide Hybrids as New Potential Tyrosinase Inhibitors

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