Bazı yeni hidrazon bileşiklerinin sentezi, karakterizasyonu ve antioksidan aktivitelerinin belirlenmesi

Bu araştırmada, bir aril sülfonat parçası (2a-i) taşıyan bazı yeni heterosiklik hidrazon bileşikleri ilk kez başarılı bir şekilde sentezlendi ve bazı spektroskopik tekniklerle (FT-IR, 1H ve 13C NMR) aydınlatıldı. Sentezlenen tüm moleküllerin asetilkolinesteraz (AChE), butirilkolinesteraz (BChE), tirozinaz enzimleri üzerindeki inhibitör potansiyelleri araştırıldı. Ayrıca tüm moleküllerin DPPH serbest radikal giderimi, ABTS katyon radikali giderimi ve CUPRAC antioksidan aktiviteleri incelendi. BChE inhibisyon aktivitesi yönteminde 2-formilfenil 4-klorobenzensülfonat (1a) (IC50=10,45 μM), 5-(dietilamino)-2-formilfenil 4-Klorobenzensülfonat (1h) (IC50=10,12 μM) ve 1-( (2-nikotinoilhidrazono)metil)naftalen-2-il 4-klorobenzensülfonat (2i) (IC50=9,89 uM), standart bileşik galantaminden daha etkili bulundu. DPPH serbest radikal giderimi testinde, 2-((2-nikotinoilhidrazono)metil)fenil 4-klorobenzensülfonat (2a) (IC50=361,03 μM) ve 5-metoksi-2-((2-nikotinoilhidrazono)metil)fenil 4-klorobenzensülfonat (2e) ( IC50=348,9 μM) en yüksek antioksidan aktiviteyi gösterdi. Öte yandan, 1a, 1h, 2i bileşikleri ve galantamin moleküllerinin moleküler elektrostatik potansiyel (MEP) haritaları incelenmiştir.

In this research, some new heterocyclic hydrazone compounds bearing an aryl sulfonate moiety (2a-i) were facilely synthesized for the first time and elucidated by some spectroscopic techniques (FT-IR, 1H- and 13C NMR). The inhibitory potentials of all synthesized molecules on acetylcholinesterase (AChE), butyrylcholinesterase (BChE), tyrosinase enzymes were investigated. Also, DPPH, ABTS and CUPRAC antioxidant activities of all molecules were examined. In BChE assay, it was determined that 2-formylphenyl 4-chlorobenzenesulfonate (1a) (IC50=10.45 μM), 5-(diethylamino)-2-formylphenyl 4-chlorobenzenesulfonate (1h) (IC50=10.12 μM), and 1-((2-nicotinoylhydrazono)methyl)naphthalen-2-yl 4-chlorobenzenesulfonate (2i) (IC50=9.89 μM) were found to be more effective than the standard compound galanthamine and donepezil. In DPPH assay, 2-((2-nicotinoylhydrazono)methyl)phenyl 4-chlorobenzenesulfonate (2a) (IC50=361.03 μM) and 5-methoxy-2-((2-nicotinoylhydrazono)methyl)phenyl 4-chlorobenzenesulfonate (2e) (IC50=348.9 μM) indicated the highest antioxidant activities. On the other hand, the molecular electrostatic potential (MEP) maps of compounds 1a, 1h, 2i and galanthamine molecules were investigated.