81511-63-9Relevant academic research and scientific papers
Novel 1,3,4-oxadiazole compounds inhibit the tyrosinase and melanin level: Synthesis, in-vitro, and in-silico studies
Vanjare, Balasaheb D.,Choi, Nam Gyu,Mahajan, Prasad G.,Raza, Hussain,Hassan, Mubashir,Han, Yohan,Yu, Seon-Mi,Kim, Song Ja,Seo, Sung-Yum,Lee, Ki Hwan
, (2021)
In this research work, we have designed and synthesized some biologically useful of 1,3,4-Oxadiazoles. The structural interpretation of the synthesized compounds has been validated by using FT-IR, LC-MS, HRMS, 1H NMR and 13C NMR techniques. Moreover, the in-vitro mushroom tyrosinase inhibitory potential of the target compounds was assessed. The in-vitro study reveals that, all compounds demonstrate an excellent tyrosinase inhibitory activity. Especially, 2-(5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-ylthio)-N-phenylacetamide (IC50 = 0.003 ± 0.00 μM) confirms much more significant potent inhibition activity compared with standard drug kojic acid (IC50 = 16.83 ± 1.16 μM). Subsequently, the most potent five oxadiazole compounds were screened for cytotoxicity study against B16F10 melanoma cells using an MTT assay method. The survival rate for the most potent compound was more pleasant than other compounds. Furthermore, the western blot results proved that the most potent compound considerably decreased the expression level of tyrosinase at 50 μM (P 0.05). The molecular docking investigation exposed that the utmost potent compound displayed the significant interactions pattern within the active region of the tyrosinase enzyme and which might be responsible for the decent inhibitory activity towards the enzyme. A molecular dynamic simulation experiment was presented to recognize the residual backbone stability of protein structure.
Interaction of 5-aryl-1,3,4-oxadiazoline-2(3H)-thiones with N-substituted chloroacetamides
Galust'Yan,Ziyaev
, p. 1104 - 1109 (2002)
The reactions of some 5-aryl-1,3,4-oxadiazoline-2(3H)-thiones (aryl = phenyl, 4-bromophenyl, 4-methylphenyl, 2,4-dichlorophenyl) with N-alkyl- and N-arylchloroacetamides has been studied. The nature of the substituents in the molecules of the thiones and the chloroacetamides does not affect the direction of the reaction but does affect the yield of the desired products.
Synthesis, carbonic anhydrase inhibition, anticancer activity, and molecular docking studies of 1,3,4-oxadiazole derivatives
Choi, Nam Gyu,Eom, Young Seok,Hassan, Mubashir,Kim, Song Ja,Lee, Ki Hwan,Raza, Hussain,Vanjare, Balasaheb D.
, (2022/04/07)
In this work, we have synthesized various organic compounds possessing 1,3,4-oxadiazole as a core structure and the structure of the newly synthesized target compounds has been revealed using different analytical approaches such as FT-IR, LCMS, and NMR (proton and carbon), respectively. The in vitro carbonic anhydrase potentials of these synthesized 17 different analogues were investigated. The result suggests that compound 7g, a 3-pyridine substituted analogue with an IC50 of 0.1?μM, was found to have the most potent carbonic inhibitory activity (11-fold more active) than the positive control (acetazolamide) with an IC50 of 1.1 ± 0.1?μM. Besides, among the series 7(a–q) approved in the identification of four potent carbonic anhydrase inhibitors with the IC50 standards varies from 0.1 to 1.0 ± 0.1?μM. Additionally, the non-competitive behaviour for potent compound 7g was analysed using the Lineweaver–Burk plot from the kinetic study. Furthermore, the anticancer activity of all the synthesized compounds screened against B16F10 melanoma cells using the MTT assay method. Additionally, the molecular docking studies revealed that 7g inhibitor shows good binding energy as well as good binding interaction pattern along with enzyme.
