Alkyl 2-(2-(arylidene)alkylhydrazinyl)thiazole-4-carboxylates: synthesis, acetyl cholinesterase inhibition and docking studies

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dc.creatorHaroon, Muhammad
dc.creatorKhalid, Muhammad
dc.creatorShahzadi, Kiran
dc.creatorAkhtar, Tashfeen
dc.creatorSaba, Sumbal
dc.creatorKhan, Jamal Rafique
dc.creatorAli, Shehbaz
dc.creatorIrfan, Muhammad
dc.creatorAlam, Mohammed Mujahid
dc.creatorImran, Muhammad
dc.date.accessioned2024-11-07T17:40:44Z
dc.date.available2024-11-07T17:40:44Z
dc.date.issued2021
dc.description.abstractA series of N-alkylated and N-benzylated thiazole-4-carboxylates (3a-n) were prepared via alkylation/benzylation of ethyl 2-(2-(arylidene)hydrazinyl)thiazole-4-carboxylates (1). The structures of all synthesized thiazoles were established with FT-IR, 1H-, 13C-NMR and HRMS spectroscopic techniques. All synthesized compounds were screened as inhibitors of acetylcholinesterase (AChE), using galanthamine as the standard. The AChE activity results revealed, that the compounds ethyl 2-(2-(4-methoxybenzylidene)(benzyl)hydrazinyl)thiazole-4-carboxylate (3n) and ethyl 2-(2-(4-methylbenzylidene)(decyl)hydrazinyl)thiazole-4-carboxylate (3k) were moderate inhibitor with IC50 values 9.56 ± 2.76 and 9.92 ± 0.96 µM, (better than the standard). Simulation studies based on virtual screening of AChE inhibition by molecular docking predicted the binding free energies and molecular inhibition of 3f, 3k and 3n compounds (∆G= -7.73, ∆G= -7.91 and ∆G= -8.13) was comparable with galanthamine. These three compounds occupied the same binding cavity as galanthamine, with greater affinity. Furthermore, in silico, all other compounds also exhibited moderate to good AChE inhibition activities.
dc.identifier.citationHAROON, Muhammad et at. Alkyl 2-(2-(arylidene)alkylhydrazinyl)thiazole-4-carboxylates: synthesis, acetyl cholinesterase inhibition and docking studies. Journal of Molecular Structure, Amsterdam, v. 1245, e131063, 2021. DOI: 10.1016/j.molstruc.2021.131063. Disponível em: https://www.sciencedirect.com/science/article/pii/S0022286021011947?via%3Dihub. Acesso em: 31 jul. 2024.
dc.identifier.doi10.1016/j.molstruc.2021.131063
dc.identifier.issne- 1872-8014
dc.identifier.issn0022-2860
dc.identifier.urihttps://www.sciencedirect.com/science/article/pii/S0022286021011947?via%3Dihub
dc.language.isoeng
dc.publisher.countryHolanda
dc.publisher.departmentInstituto de Química - IQ (RMG)
dc.rightsAcesso Restrito
dc.subjectAcetylcholinesterase activity
dc.subjectThiazole-4-carboxylates
dc.subjectN-alkylated thiazoles
dc.subjectN-benzylated thiazoles
dc.titleAlkyl 2-(2-(arylidene)alkylhydrazinyl)thiazole-4-carboxylates: synthesis, acetyl cholinesterase inhibition and docking studies
dc.typeArtigo

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