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Synthesis, Spectroscopic Analysis, Biological Evaluation, and In Silico Studies of Novel Benzenesulfonate-Derived Schiff-Mannich Bases    
Yazarlar (6)
Dr. Öğr. Üyesi Ahmet HARMANKAYA Dr. Öğr. Üyesi Ahmet HARMANKAYA
Türkiye
Namık Kılınç
Türkiye
Doç. Dr. Murat BEYTUR Doç. Dr. Murat BEYTUR
Kafkas Üniversitesi, Türkiye
Yonca Yılmaz
Doç. Dr. Sevda MANAP Doç. Dr. Sevda MANAP
Kafkas Üniversitesi, Türkiye
Prof. Dr. Haydar YÜKSEK Prof. Dr. Haydar YÜKSEK
Kafkas Üniversitesi, Türkiye
Devamını Göster
Özet
In the current study, 3-formyl phenyl benzenesulfonate is created by reacting 3-hydroxybenzaldehyde with benzene sulfonyl chloride, which is aided by triethylamine. Nine unique (Z)-3-[(3-substituted-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)-iminomethyl] compounds were formed through the reaction of a manufactured 3-formyl phenyl benzenesulfonate chemical with nine 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-one, as detailed in the existing literature. Phenyl benzene sulfonate (S) compounds were purchased. Through the reaction of the Schiff bases that were made a secondary amine, such as morpholine with formaldehyde, heterocyclic Mannich bases of a unique kind were created. Five recently found (Z)-3-[(3-substituted-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)-iminomethyl] compounds are presented in this work. By reacting phenyl benzene sulfonate (S) with morpholine in the presence of formaldehyde, five new (Z)-3-[(3-substituted-1(morpholinomethyl)-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)-iminomethyl] compounds were created. Chemical compounds fall under the category of phenylbenzene sulfonates (M). Utilizing IR, 1H NMR, and 13C NMR spectroscopy, fourteen recently novel compounds' chemical structures were examined. The ability of the freshly synthesized Schiff and morpholine-derived Mannich bases to obstruct the aldose reductase enzyme's (AR) activity was also assessed. The 1,2,4-triazole functional group was modified by adding various groups at the 1 and 3 positions, resulting in a collection of compounds (S1–9 and M1, 2, 4, 5, 7). It was determined whether these synthetic compounds could prevent the human recombinant AR enzyme from working in vitro, and the findings were validated using molecular docking, molecular mechanics, and ADME analyses. To better understand this mechanism, synthetic Schiff and Mannich base derivatives as well as the positive control substance quercetin were tested using molecular docking against the human recombinant AR enzyme in vitro. To assess the drug-like properties of Schiff and Mannich base analogs, a series of absorption, distribution, metabolism, and excretion (ADME) properties were analyzed theoretically.
Anahtar Kelimeler
1,2,4-Triazole ring | Benzenesulfonate | Docking Study | Inhibitory activity | Mannich Bases | Schiff base
Makale Türü Özgün Makale
Makale Alt Türü SSCI, AHCI, SCI, SCI-Exp dergilerinde yayımlanan tam makale
Dergi Adı Chemical Society of Pakistan
Dergi ISSN 0253-5106 Wos Dergi Scopus Dergi
Dergi Tarandığı Indeksler SCI-Expanded
Dergi Grubu Q4
Makale Dili Türkçe
Basım Tarihi 01-2023
Cilt No 45
Sayı 4
Sayfalar 323 / 335
Doi Numarası 10.52568/001280/jcsp/45.04.2023
Makale Linki http://dx.doi.org/10.52568/001280/jcsp/45.04.2023