Yeni bazı flavonoid türevlerinin sentezi, kimyasal yapılarının aydınlatılması ve monoamin oksidaz enzimleri üzerine etkilerinin araştırılması
| dc.contributor.advisor | Ertan, Rahmiye | |
| dc.contributor.author | Evranos, Begüm | |
| dc.date.accessioned | 2019-02-07T22:24:27Z | |
| dc.date.available | 2010 | |
| dc.date.available | 2019-02-07T22:24:27Z | |
| dc.date.issued | 2010 | |
| dc.description.abstract | Bu çalışmada, asetofenon (Ia-j) ve benzaldehit (IIa-d) türevlerinin metanol içinde KOH varlığında reaksiyonu ile şalkon türevleri (IIIa-u) elde edilmiş, elde edilen şalkonların etanol içinde hidrazit türevleriyle (IVa-f) ısıtılmasıyla hidrazon (Va-s) ve 2-pirazolin (VIa-u) yapısında bazı yeni moleküllerin sentezleri gerçekleştirilmiştir. Böylece şalkon (2), hidrazon (18) ve 2-pirazolin (20) türevleri olan toplam 40 orijinal kimyasal madde elde edilmiş ve bunların yapı tayinlerinde Elementel Analiz, IR, 1H-NMR ve Mass spektral yöntemlerinden yararlanılmıştır. Sentezlenen bileşiklerin, MAO enzimi üzerindeki inhibisyon yapıcı etkileri incelenmiş ve sonuçta VIa, VIc, VIf ve VIl bileşiklerinin referans bileşik moklobemide yakın düzeyde MAO-A enzimi üzerinde inhibisyon yapıcı etki gösterdikleri saptanmıştır. Sentezlenen orijinal bileşiklerin kimyasal okunuşları aşağıda bir arada verilmiştir; IIIc (E)-1-(3,5-dikloro-2-hidroksifenil)-3-m-tolilprop-2-en-1-on IIIo (E)-1-(4-bromofenil)-3-m-tolilprop-2-en-1-on Va (E)-N'-((E)-1-(2,4-dimetoksifenil)-3-p-tolilalliliden)tiyofen-2-karbohidrazid Vb (E)-N'-((E)-1-(2,4-dimetoksifenil)-3-p-tolilalliliden)furan-2-karbohidrazid Vc (E)-N'-((E)-1-(4-florofenil)-3-(4-metoksifenil)alliliden)tiyofen-2-karbohidrazid Vd (E)-N'-((E)-1-(4-florofenil)-3-(4-metoksifenil)alliliden)-4-metil-1,2,3-tiyadiazol-5- karbohidrazid Ve (E)-N'-((E)-1-(4-florofenil)-3-p-tolilalliliden)tiyofen-2-karbohidrazid Vf (E)-N'-((E)-1-(4-florofenil)-3-m-tolilalliliden)tiyofen-2-karbohidrazid Vg (E)-N'-((E)-1-(4-bromofenil)-3-p-tolilalliliden)tiyofen-2-karbohidrazid Vh (E)-N'-((E)-1-(4-bromofenil)-3-p-tolilalliliden)-4-metil-1,2,3-tiyadiazol-5-karbohidrazid Vi (E)-N'-((E)-1-(4-bromofenil)-3-(4-metoksifenil)alliliden)-4-metoksibenzohidrazid Vj (E)-N'-((E)-1-(4-bromofenil)-3-m-tolilalliliden)-4-metil-1,2,3-tiyadiazol-5-karbohidrazid Vk (E)-N'-((E)-1-(4-bromofenil)-3-(4-metoksifenil)alliliden)furan-2-karbohidrazid Vl (E)-N'-((E)-1-(4-klorofenil)-3-p-tolilalliliden)tiyofen-2-karbohidrazid Vm (E)-N'-((E)-1-(4-klorofenil)-3-p-tolilalliliden)-4-metil-1,2,3-tiyadiazole-5-karbohidrazid Vn (E)-N'-((E)-1-(4-klorofenil)-3-m-tolilalliliden)-4-metil-1,2,3-tiyadiazole-5-karbohidrazid Vo (E)-N'-((E)-1-(4-klorofenil)-3-(4-metoksifenil)alliliden)-4-metil-1,2,3-tiyadiazol-5-karbohidrazid Vp (E)-N'-((E)-1-(4-klorofenil)-3-(4-metoksifenil)alliliden)-4-metoksibenzohidrazid Vr (E)-N'-((E)-1-(4-hidroksifenil)-3-p-tolilalliliden)-4-metil-1,2,3-tiyadiazol-5- karbohidrazid Vs (E)-N'-((E)-1-(4-metoksifenil)-3-p-tolilalliliden)-4-metil-1,2,3-tiyadiazol-5-karbohidrazid VIa (3-(5-kloro-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(piridin-4-il) metanon VIb (3-(5-kloro-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(furan-2- il)metanon VIc (3-(5-kloro-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(fenil) metanon VId (3-(5-kloro-2-hidroksifenill)-5-p-tolil-4,5-dihidropirazol-1-il)(4-metoksifenil) metanon VIe (3-(5-kloro-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(4-metil-1,2,3-tiyadiazol-5-il)metanon VIf (3-(3,5-dikloro-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(4-metoksifenil) metanon VIg (3-(3,5-dikloro-2-hidroksifenil)-5-m-tolil-4,5-dihidropirazol-1-il)(piridin-4-il) metanon VIh (3-(3,5-dikloro-2-hidroksifenil)-5-m-tolil-4,5-dihidropirazol-1-il)(furan-2-il) metanon VIi (3-(3,5-dikloro-2-hidroksifenil)-5-m-tolil-4,5-dihidropirazol-1-il)(fenil) metanon VIj (3-(3,5-dikloro-2-hidroksifenil)-5-m-tolil-4,5-dihidropirazol-1-il)(4-metoksifenil) metanon VIk (3-(3,5-dikloro-2-hidroksifenil)-5-m-tolil-4,5-dihidropirazol-1-il)(4-metil-1,2,3-tiyadiazol-5-il)metanon VIl (3-(5-bromo-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(piridin-4-il)metanon VIm (3-(5-bromo-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(furan-2-il) metanon VIn (3-(5-bromo-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(fenil)metanon VIo (3-(5-bromo-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(4-metoksifenil) metanon VIp (3-(5-Bromo-2-hidroksifenil)-5-p-tolil-4,5-dihidropirazol-1-il)(tiyofen-2-il) metanon VIr (3-(2-hidroksi-4-metoksifenil)-5-(2-metoksifenil)-4,5-dihidropirazol-1-il)(fenil) metanon VIs (3-(2-hidroksi-4-metoksifenil)-5-(4-metoksifenil)-4,5-dihidropirazol-1-il)(4-metoksifenil)metanon VIt (3-(5-bromo-2-hidroksifenil)-5-(4-metoksifenil)-4,5-dihidropirazol-1-il)(4-metoksifenil)metanon VIu (3-(5-kloro-2-hidroksifenil)-5-(4-metoksifenil)-4,5-dihidropirazol-1-il)(tiyofen-2-il) metanon.AbstractIn this study, chalcone derivatives (IIIa-u) were prepared with the reaction of some acetophenone (Ia-j) and benzaldehyde derivatives (IIa-d) in KOH/MeOH. The ensuing chalcone derivatives (IIIa-u) are then reacted with some hydrazide compounds to furnish hydrazone (Va-s) and 2-pyrazoline (VIa-u) derivatives. The structure of synthesized original chalcone (2), hydrazone (18) and 2-pyrazoline (20) derivatives was elucidated by IR, 1H NMR, Mass spectral data and elementary analysis findings. The synthesized compounds were tested for their MAO inhibitor activities and it is found that compounds VIa, VIc, VIf and VIl have similar activities as moclobemide. Chemical names of synthesized compounds are given below; IIIc (E)-1-(3,5-Dichloro-2-hydroxyphenyl)-3-m-tolylprop-2-en-1-one IIIo (E)-1-(4-Bromophenyl)-3-m-tolylprop-2-en-1-on Va (E)-N'-((E)-1-(2,4-Dimethoxyphenyl)-3-p-tolylallylidene)thiophene-2-carbohydrazide Vb (E)-N'-((E)-1-(2,4-Dimethoxyphenyl)-3-p-tolylallylidene)furan-2-carbohydrazide Vc (E)-N'-((E)-1-(4-Fluorophenyl)-3-(4-methoxyphenyl)allylidene)thiophene-2-carbohydrazide Vd (E)-N'-((E)-1-(4-Fluorophenyl)-3-(4-methoxyphenyl)allylidene)-4-methyl-1,2,3-thiadiazole-5-carbohydrazide Ve (E)-N'-((E)-1-(4-Fluorophenyl)-3-p-tolylallylidene)thiophene-2-carbohydrazide Vf (E)-N'-((E)-1-(4-Fluorophenyl)-3-m-tolylallylidene)thiophene-2-carbohydrazide Vg (E)-N'-((E)-1-(4-Bromophenyl)-3-p-tolylallylidene)thiophene-2-carbohydrazide Vh (E)-N'-((E)-1-(4-Bromophenyl)-3-p- tolylallylidene)-4-methyl-1,2,3-thiadiazole-5-carbohidrazide Vi (E)-N'-((E)-1-(4-Bromophenyl)-3-(4-methoxyphenyl)allylidene)-4-methoxy benzohydrazide Vj (E)-N'-((E)-1-(4-Bromophenyl)-3-m-tolylallylidene)-4-methyl-1,2,3-thiadiazole-5-carbohidrazide Vk (E)-N'-((E)-1-(4-Bromophenyl)-3-(4-methoxyphenyl)allylidene)furan-2-carbohydrazide Vl (E)-N'-((E)-1-(4-Chlorophenyl)-3-p-tolylallylidene)thiophene-2-carbohydrazide Vm (E)-N'-((E)-1-(4-Chlorophenyl)-3-p-tolylallylidene)-4-methyl-1,2,3-thiadiazole-5-carbohidrazide Vn (E)-N'-((E)-1-(4-Chlorophenyl)-3-m-tolylallylidene)-4-methyl-1,2,3-thiadiazole-5-carbohidrazide Vo (E)-N'-((E)-1-(4-Chlorophenyl)-3-(4-metoxyphenyl)allylidene)-4-methyl-1,2,3-thiadiazole-5-carbohidrazide Vp (E)-N'-((E)-1-(4-Chlorophenyl)-3-(4-metoxypheny)allylidene)-4-metoxybenzohidrazide Vr (E)-N'-((E)-1-(4-Hydroxyphenyl)-3-p-tolylallylidene)-4-methyl-1,2,3-thiadiazole-5- carbohidrazide Vs (E)-N'-((E)-1-(4-Metoxyphenyl)-3-p-tolylallylidene)-4-methyl-1,2,3-thiadiazole-5-carbohidrazide VIa (3-(5-Chloro-2-hidroxyphenyl)-5-p-tolyl-4,5-dihydropyrazole-1-yl)(pyridine-4-yl) methanone VIb (3-(5-Chloro-2-hidroxyphenyl)-5-p-tolyl-4,5-dihydropyrazole-1-yl)(furan-2- yl)methanone VIc (3-(5-Chloro-2-hydroxyphenyl)-5-p-tolyl-4,5-dihydropyrazole-1-yl)(phenyl) methanone VId (3-(5-Chloro-2-hydroxyphenyl)-5-p-tolyl-4,5-dihydropyrazole-1-yl)(4-metoxyphenyl) methanone VIe (3-(5-Chloro-2-hydroxyphenyl)-5-p-tolyl-4,5-dihidropyrazole-1-yl)(4-methyl-1,2,3-thiadiazole-5-yl)methanone VIf (3-(3,5-Dichloro-2-hydroxyphenyl)-5-p-tolyl-4,5-dihydropyrazole-1-yl)(4-metoxyphenyl) methanone VIg (3-(3,5-Dichloro-2-hydroxyphenyl)-5-m-tolyl-4,5-dihidropyrazole-1-il)(pyridine-4-il) metanone VIh (3-(3,5-Dichloro-2-hydroxyphenyl)-5-m-tolyl-4,5-dihidropyrazole-1-yl)(furan-2-yl) methanone VIi (3-(3,5-Dichloro-2-hydroxyphenyl)-5-m-tolyl-4,5-dihydropyrazole-1-yl)(phenyl) methanone VIj (3-(3,5-Dichloro-2-hydroxyphenyl)-5-m-tolyl-4,5-dihydropyrazole-1-yl)(4-metoxyphenyl) methanone VIk (3-(3,5-Dichloro-2-hydroxyphenyl)-5-m-tolyl-4,5-dihydropyrazole-1-yl)(4-methyl-1,2,3-thiadiazole-5-yl)methanone VIl (3-(5-Bromo-2-hydroxyphenyl)-5-p-tolyl-4,5-dihydropyrazol-1-yl)(pyridine-4-yl)methanone VIm (3-(5-Bromo-2-hydroxyphenyl)-5-p-tolyl-4,5-dihydropyrazol-1-yl)(furan-2-yl) methanone VIn (3-(5-Bromo-2-hydroxyphenyl)-5-p-tolyl-4,5-dihydropyrazol-1-yl)(phenyl)methanone VIo (3-(5-Bromo-2-hydroxyphenyl)-5-p-tolyl-4,5-dihydropyrazol-1-yl)(4-metoxyphenyl) methanone VIp (3-(5-Bromo-2-hydroxypheny)-5-p-tolyl-4,5-dihydropyrazol-1-yl)(thiophene-2-yl) methanone VIr (3-(2-Hydroxy-4-metoxyphenyl)-5-(2-metoxyphenyl)-4,5-dihydropyrazol-1-yl)(phenyl) methanone VIs (3-(2-Hydroxy-4-metoxyphenyl)-5-(4-metoxyphenyl)-4,5-dihydropyrazol-1-yl)(4-metoxyphenyl)methanone VIt (3-(5-Bromo-2-hydroxyphenyl)-5-(4-metoxyphenyl)-4,5-dihydropyrazol-1-yl)(4-metoxyphenyl)methanone VIu (3-(5-Chloro-2-hydroxyphenyl)-5-(4-metoxyphenyl)-4,5-dihydropyrazol-1-yl)(thiophen-2-yl) methanone | |
| dc.identifier.uri | http://hdl.handle.net/20.500.12575/35269 | |
| dc.language.iso | tr | TR_tr |
| dc.publisher | Sağlık Bilimleri Enstitüsü | |
| dc.subject | TIP, Eczaneler ve medikal depolar | tr |
| dc.title | Yeni bazı flavonoid türevlerinin sentezi, kimyasal yapılarının aydınlatılması ve monoamin oksidaz enzimleri üzerine etkilerinin araştırılması | |
| dc.type | doctoralThesis |