Novel thiazolyl-hydrazone derivatives including piperazine ring: synthesis, in vitro evaluation, and molecular docking as selective MAO-A inhibitor.

Szczegóły
Abstrakt

Tytuł:: Novel thiazolyl-hydrazone derivatives including piperazine ring: synthesis, in vitro evaluation, and molecular docking as selective MAO-A inhibitor.
Autorzy:: Osmaniye D; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, Eskişehir 26470, Turkey.; Doping and Narcotic Compounds Analysis Laboratory, Faculty of Pharmacy, Anadolu University, Eskişehir 26470, Turkey.
Alaşan R; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, Eskişehir 26470, Turkey.
Sağlık BN; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, Eskişehir 26470, Turkey.; Doping and Narcotic Compounds Analysis Laboratory, Faculty of Pharmacy, Anadolu University, Eskişehir 26470, Turkey.
Levent S; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, Eskişehir 26470, Turkey.; Doping and Narcotic Compounds Analysis Laboratory, Faculty of Pharmacy, Anadolu University, Eskişehir 26470, Turkey.
Özkay Y; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, Eskişehir 26470, Turkey.; Doping and Narcotic Compounds Analysis Laboratory, Faculty of Pharmacy, Anadolu University, Eskişehir 26470, Turkey.
Kaplancıklı ZA; Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, Eskişehir 26470, Turkey.
Źródło:: Zeitschrift fur Naturforschung. C, Journal of biosciences [Z Naturforsch C J Biosci] 2021 Oct 21; Vol. 77 (3-4), pp. 167-175. Date of Electronic Publication: 2021 Oct 21 (Print Publication: 2022).
Typ publikacji:: Journal Article
Język:: English
Imprint Name(s):: Publication: Berlin : De Gruyter
Original Publication: Tübingen : Verlag der Zeitschrift für Naturforschung, 1986-
MeSH Terms:: Hydrazones*/chemistry
Hydrazones*/pharmacology
Monoamine Oxidase*
Molecular Docking Simulation ; Molecular Structure ; Piperazine ; Structure-Activity Relationship
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Contributed Indexing:: Keywords: hMAO enzymes; 2D-NMR; molecular docking; piperazine; thiazolyl-hydrazone
Substance Nomenclature:: 0 (Hydrazones)
1RTM4PAL0V (Piperazine)
EC 1.4.3.4 (Monoamine Oxidase)
Entry Date(s):: Date Created: 20211021 Date Completed: 20220310 Latest Revision: 20220311
Update Code:: 20240105
DOI:: 10.1515/znc-2021-0223
PMID:: 34674410
: Czasopismo naukowe

MAO-A inhibitors are used in the treatment of depression. There are many studies showing that the thiazolyl-hydrazone structure is a pharmacophore structure for the MAO enzyme. In previous studies by our team, activity studies were carried out with thiazolyl-hydrazone derivatives containing pyrrolidine, morpholine, and piperazine. All of them were displayed MAO-A selective inhibition profile. Additionally, derivatives containing piperazine ring were most active. For this purpose, thiazolyl-hydrazone derivatives containing piperazine were synthesized, but this time an active group, formyl group, was added to the piperazine ring as a substituent. Based on this view, new thiazolyl-hydrazone compounds were synthesized, characterized, and screened for their h MAO-A and h MAO-B inhibitory activity by an in vitro fluorometric method. The structure of the compound was tried to be fully elucidated using 2D NMR technique. The compound including 2,4-dimethyl substituent ( 3i ) were found to be the most effective agents in the series against MAO-A enzyme with the IC 50 value of 0.080 ± 0.003 µM. The docking study of compound 3i revealed that there is a strong interaction between the active sites of h MAO-A and analyzed compound.
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