Hidroksil amin ile çift bağların Diels-Alder katılmasından oluşan yeni moleküllerin sentezi

Abstract

Şalkonlar (flavonoidler), meyveler, sebzeler ve çeşitli yararlı biyokimya üzerinde antioksidan etkiye sahip, fizyolojik düzenleyiciler veya hücre döngüsünün inhibitörleri olarak kimyasal haberci olarak etki gösteren aromatik pigment bileşikleridir. Flavonoidlerin son yıllarda çeşitli kimyasal yapılardaki (pirazolin, oksadiazol, kumarin, ksantin, şalkon vb.) MAO-B (monoamin oksidazlar B izoformu) inhibitörü bileşiklerin gelişimi, yapı-aktivite ilişkileri ve nörodejeneratif hastalıklardaki incelemeleri dikkat çekmektedir. Tüm bu bilgiler ışığında 4-hidroksibenzaldehit ile benzil klorür DMF varlığında 4-(benzyloxy)benzaldehyde (1) eldesinden yola çıkarak, bu moleküle SOCl2 ve etanol ilave edilerek (E)-3-(4-(benzyloxy)phenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one (2) nolu molekülün sentezi gerçekleştirildi. 2 nolu molekülden (1Z,2E)-3-(4-(benzyloxy)phenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one oxime (3) molekülü hidroksilamin hidroklorür reaktifi kullanılarak sentezlendi. 3 nolu molekül DDQ reaktifi kullanılarak halka kapanması sonucunda 4-(5-(4-(benzyloxy)phenyl)isoxazol-3-yl)phenol (4) elde edildi. Takip eden reaksiyonda ise asetatlama reaksiyonu ile 4-(5-(4-(benzyloxy)phenyl)isoxazol-3-yl)phenyl acetate (5) nolu molekül, son olarak da 4 nolu molekül akriloil klorür ve trietilamin reaktifi ile muamele edilerek çift bağların Diels-Alder katılma yöntemiyle 4-(5-(4-(benzyloxy)phenyl)isoxazol-3-yl)phenyl acrylate (6) elde edilerek yeni molekül sentezlendi. Elde edilen son molekül için sensör özelliği incelendi. Tüm metallere karşı sensör özellik bakıldı ve "turn off" olan moleküle (6) amino asitle (sistein) muamele edilerek "turn on" olması sağlandı. Sentezlenen moleküller, 1H NMR, 13C NMR ve FT-IR spektroskopik verileri kullanılarak karakterize edildi.

Chalcones (flavonoids) are aromatic pigment compounds that have an antioxidant effect on fruits, vegetables and various beneficial biochemistry, acting as chemical messengers as physiological regulators or inhibitors of the cell cycle. The development of MAO-B (monoamine oxidases B isoform) inhibitor compounds in various chemical structures (pyrazoline, oxadiazole, coumarin, xanthine, chalcone, etc.), structure-activity relationships and neurodegenerative diseases have attracted attention in recent years. In the light of all this information, starting from the obtaining of 4- (benzyloxy) benzaldehyde (1) in the presence of 4-hydroxybenzaldehyde and benzyl chloride DMF, SOCl2 and ethanol were added to this molecule and synthesis of the molecule (E)-3-(4-(benzyloxy)phenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one (2) was performed. The molecule number 2 (1Z, 2E) -3- (4- (benzyloxy) phenyl) -1- (4-hydroxyphenyl) prop-2-en-1-one oxime (3) molecule was synthesized using hydroxylamine hydrochloride reagent. As a result of ring closure using 3 molecule DDQ reagent, 4- (5- (4- (benzyloxy) phenyl) isoxazol-3-yl) phenol (4) was obtained. In the following reaction, 4- (5- (4- (benzyloxy) phenyl) isoxazol-3-yl) phenyl acetate (5) molecule was obtained by the acetate reaction. Finally, the molecule number 4 was treated with acryloyl chloride and triethylamine reagent and 4- (5- (4- (benzyloxy) phenyl) isoxazol-3-yl) phenyl acrylate (6) was obtained by the Diels-Alder addition method of double bonds and the new molecule was synthesized. .The sensor property was examined for the last molecule obtained. Sensory properties against all metals were examined and the molecule that was "turn off" (6) was treated with amino acid (cysteine) and turned on. The synthesized molecules were characterized using 1H NMR, 13C NMR and FT-IR spectroscopic data.