Browsing by Author "Ertan, Rahmiye"

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    3-(4-Chlorobenzyl)-5-(4-oxo-4H-chromen-3-ylmethylene)-1,3-thiazolidine-2,4-dione
    (2005) Bozdağ Dündar, Oya; Ertan, Rahmiye; Ünlüsoy, Meltem Ceylan; Eczacılık Fakültesi
    In the title mol­ecule, C20H12ClNO4S, the benzopyran ring system and the thia­zolidine ring are planar. The dihedral angle between the chloro­benzyl and thia­zolidine rings is 74.42 (8)°. The crystal structure is stabilized by intermolecular C-H...O hydrogen bonds.
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    3-Ethyl-5-(4-oxochroman-3-ylmethylene)- 1,3-imidazolidine-2,4-dione
    (2007) Ünlüsoy, Meltem Ceylan; Ertan, Rahmiye; Eczacılık Fakültesi
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    3-Methyl-5-(4-oxo-4H-chromen-3-ylmethylene)-1,3-thiazolidine-2,4-dione
    (2006) Ünlüsoy, Meltem Ceylan; Ertan, Rahmiye; Eczacılık Fakültesi
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    Antidiyabetik etkili yeni bazı kimyasal bileşikler üzerinde araştırmalar
    (Sağlık Bilimleri Enstitüsü, 1998) Dündar, Oya Bozdağ; Ertan, Rahmiye
    Antidiyabetik Etkili Yeni Bazı Kimyasal Bileşikler Üzerinde Araştırmalar Bu çalışmada, flavon çekirdeğinin B halkasının m-konumunda SÜ bileşikleri ile m- veya p-konumunda 2,4-TZD ve analog halkalar taşıyan yeni bazı flavonoid türevlerinin sentezleri ve bunların antidiyabetik aktivitelerinin incelenmesi amaçlandı. Bileşiklerin sentezi: 3'-Flavonil SÜ grubu için; 1.3'-Flavon sülfonamid sentezi gerçekleştirildi. 2. Daha sonra bu bileşikten hareketle 3'-flavonil SÜ türevi 7 orjinal bileşik elde edildi. H:1-(3'-Flavon)sülfonil-3-etilüre l2:1-(3'-Flavon)sülfonil-3-allilüre l3:1-(3'-Flavon)sülfonil-3-izopropilüre l4:1-(3'-Flavon)sülfonil-3-n-butilüre l5:1-(3'-Flavon)sülfonil-3-sikloheksilüre l6:1-(3'-Flavon)sülfonil-3-fenilüre l7:1-(3'-Flavon)sülfonil-3-p-tolilüre Flavonil 3' (veya 4')-2,4-TZD ve analogları grubu için; 1.Flavon-3' (veya 4')-bromometil sentezi gerçekleştirildi. 2. Bu bileşik ile; a-2,4-TZD halkasının reaksiyonu sonucu flavon ve 2,4-TZD arasında metilen köprüsü bulunan türevlerin sentezi gerçekleştirildi. b-Ayrıca, bu bileşiğin 3' (veya 4')-bromometil grubunun aldehite dönüştürülmesini takiben 2,4-TZD, 2,4-imidazolidindion ve 2-tiyohidantoin halkaları ile Knoevenagel reaksiyonu sonucu flavon ve sözü edilen halkalar arasında metin köprüsünün olduğu bileşikler sentez edildi. Elde edilen bu grup bileşikler, etil veya metil iyodür ile reaksiyonu sonucu N-alkil sübstitüe türevleri hazırlandı. Bu 2 farklı genel yöntem ile 10 adet flavonun m-konumundan, 10 adet de p-konumundan olmak üzere toplam 20 orjinal kimyasal bileşiğe ulaşıldı. 192 H3:3-Metil-5-[3'-(4H-4-okso-1-benzopiran-2-il)benziliden]-2,4-TZD H4:3-Etil-5-[3'-(4H-4-okso-1-benzopiran-2-il)benziliden]-2,4-TZD ll5:5-[3'-(4H-4-okso-1-benzopiran-2-il)benziliden]-2,4-imidazoliclindion II6:1,3-Dimetil-5-[3'-(4H-4-okso-1-benzopiran-2-il)benziliden]-2,4- imidazolidindion U7:3-Etil-5-[3'-(4H-4-okso-1-benzopiran-2-il)benziliden]-2,4- imidazolidindion H8:5-[3'-(4H-4-okso-1-benzopiran-2-il)benziliden]-2-tiyohidantoin 119:1, 3-Dimetil-5-[3'-(4H-4-okso-1-benzopiran-2-il)benziliden]-2- tiyohidantoin H10:3-Etil-5-[3'-(4H-4-okso-1-benzopiran-2-il)benziliden]-2-tiyohidantoin IIH:5-[4'-(4H-4-okso-1-benzopiran-2-il)benzil]-2,4-TZD lll2:5-[4'-(4H-4-okso-1-benzopiran-2-il)benziliden]-2,4-TZD IH3:3-Metil-5-[4'-(4H-4-okso-1-benzopiran-2-il)benziliden]-2,4-TZD lll4:3-Etil-5-[3'-(4H-4-okso-1-benzopiran-2-il)benziliden]-2,4-TZD HI5:5-[4'-(4H-4-okso-1-benzopiran-2-il)benziliden]-2,4-imidazolidindion NI6:1,3-Dimetil-5-[4'-(4H-4-okso-1-benzopiran-2-il)benziliden]-2,4- imidazolidindion 1117:1, 3-Dietil-5-[4'-(4H-4-okso-1-benzopiran-2-il)benziliden]-2, 4- imidazolidindion IH8:5-[4'-(4H-4-okso-1-benzopiran-2-il)benziliden]-2-tiyohidantoin 1119 :1,3-Dimetil-5-[4'-(4H-4-okso-1-benzopiran-2-i I) benzi liden]-2- tiyohidantoin 11110:1,3-Dietil-5-[4'-(4H-4-okso-1-benzopiran-2-il)benziliden]-2-tiyohidantoin Elde edilen bileşiklerin saflıkları İTK ile kontrol edildikten sonra ergime noktaları saptandı ve yapıları İR, 1H NMR, Mass ve Elementel Analiz verileri ile kanıtlandı. 3'-flavonil SÜ grubu bileşiklerin başlangıç maddesini oluşturan 3'-flavonsülfonamidin ayrıca X Işınları Kırınımı ile konformasyonel analizi gerçekleştirilerek bu grup bileşiklerin SÜ reseptörü ile etkileşiminin değerlendirmesi yapıldı. Buna göre, flavonil SÜ grubu bileşiklerin biyolojik etki için SÜ reseptörünün A ve B yöresi ile etkileşebilecek durumda olabileceği, biyolojik deneyler sonucunda da flavonil SÜ grubu bileşiklerin insülin salgı lattırıcı aktiviteye sahip oldukları görüldü. Abstract Studies on Some Chemical Compounds With Antidiabetic Activity In this study, it was aimed to investigate the synthesis and the antidiabetic activity of some new flavone derivatives which contain of SU compounds moiety at m- position, 2,4-TZD and analog rings at m- or p- position of B ring of flavone nucleus. Synthesis of the compounds: For 3'-Flavonyl-SU; 1. 3'-Flavon sulfonamide was synthesized. 2. Starting from this compound 7 original 3'-flavonyl SU derivatives were synthesized. H:1-(3'-Flavone)sulfonyl-3-ethylurea l2:1-(3'-Flavone)sulfonyl-3-allylurea I3:1-(3'-Flavone)sulfonyl-3-isopropylurea l4:1-(3'-Flavone)sulfonyl-3-n-butylurea l5:1-(3'-Flavone)sulfonyl-3-cyclohexylurea l6:1-(3'-Flavone)sulfonyl-3-phenylurea l7:1-(3'-Flavone)sulfonyl-3-p-tolylurea For flavonyl 3' (or 4')-2,4-TZD and analogs; 1. Flavon-3' (or 4')bromomethyl was synthesized. 2a. The derivatives which contain methylen link between flavone and 2,4-TZD were synthesized with reaction of this compound and 2,4-TZD ring. 2b. However, after changing the 3' (or 4')-bromomethyl group of this compound to aldehyde group and condensation of this compound with 2,4-TZD, 2,4-imidazolidinedione and 2-thiohydantoine rings by Knoevenagel reaction the derivatives which contain methyn link between flavone and these ring systems were synthesized. The reaction of this group of compounds with ethyl or methyl iodide, N-alkyl substituted derivatives were prepared. By using these 2 different general methods, 20 original compounds were synthesized. 10 of these compounds were from m- position and 10 of them were from p- position of the flavone ring. 194 IM:5-[3'-(4H-4-oxo-1-benzopyran-2-yl)benzyl]-2l4-TZD H2:5-[3'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2,4-TZD U3:3-Methyl-5-[3'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2,4-TZD ll4:3-Ethyl-5-[3'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2,4-TZD H5:5-[3'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2,4-imidazolidinedione H6:1,3-Dimethyl-5-[3'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2,4- imidazolidinedione H7:3-Ethyl-5-[3'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2,4- imidazolidinedione H8:5-[3'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2-thiohydantoin U9:1,3-Dimethyl-5-[3'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2- thiohydantoin IM0:3-Ethyl-5-[3'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2- thiohydantoin IIM:5-[4'-(4H-4-oxo-1-benzopyran-2-yl)benzyl]-2,4-TZD IH2:5-[4'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2,4-TZD IU3:3-Methyl-5-[4'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2,4-TZD HI4:3-Ethyl-5-[3'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2,4-TZD IH5:5-[4'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2,4-imidazolidinedione HI6:1,3-Dimethyl-5-[4'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2,4- imidazolidinedione HI7:1,3-Diethyl-5-[4'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2,4- imidazolidinedione IH8:5-[4'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2- thiohydantoin MI9:1,3-Dimethyl-5-[4'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2- thiohydantoin 1111 0:1, 3-Diethyl-5-[4'-(4H-4-oxo-1-benzopyran-2-yl)benzyliden]-2- thiohydantoin The purity were controlled by TLC and then melting points were determined. The chemical structure of the synthesized compounds were elucidated by their İR, 1H NMR, Mass and Elemantary analysis data. Conformationally structure of compound 3'-flavonesulfonamide which was the starting substance for 3' flavonyl SU group was performed by X-Ray analysis and interaction of this group compounds with SU receptors was examined. According to this, it was seen that flavonyl SU group compounds interact with A and B side of SU receptors for the biological activity and results of biological assays showed that flavonyl SU group compounds have insulin releasing activity.
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    Antidiyabetik etkili yeni bazı kromonil-tiyazolidindion türevleri üzerinde araştırmalar
    (Sağlık Bilimleri Enstitüsü, 2009) Ceylan Ünlüsoy, Meltem; Ertan, Rahmiye
    Bu çalışmada, 2/3-formil kromon (Ia-b) ile 2,4-tiyazolidindion / imidazolidindion / 2-tiyokso-imidazolin-4-on (IIa-c) halkalarının Knoevenagel kondensasyonu yöntemi kullanılarak reaksiyona sokulmasıyla elde edilen türevlerin (IIIa-c, IVa-c) daha sonra etil veya metil iyodür ile alkilasyonu sonucunda bir seri tekabül eden N-alkil ve S-alkil kromonil-2,4-tiyazolidindion / imidazolidindion / 2-tiyokso-imidazolin-4-on (IIId-i, IVd-i) bileşikleri sentezlenmiştir. Böylece elde edilen toplam 18 orijinal kimyasal maddenin yapı tayinlerinde Elementel Analiz, IR, 1H-NMR, Mass spektral yöntemlerine ilaveten IVd, IVg ve IVi bileşikleri için de X-Işınları kristallografik incelemelerinden yararlanılmıştır. Sentezlenen bileşikler, insülinotropik etki yönünden incelenmiş ve sonuçta IVb, IVc bileşikleri, düşük konsantrasyonda (1 μg/ml), 5.6 mmol/l glukoz varlığında referans bileşik Glibenklamid’den biraz daha yüksek insülin salgılattırıcı aktivite göstermişlerdir. Sentezlenen bileşiklerin kimyasal okunuşları aşağıda topluca bir arada verilmiştir;IIIa5-(4-Okso-4H-kromen-2-il metilen)-tiyazolidin-2,4-dionIIIb5-(4-Okso-4H-kromen-2-il metilen)-imidazolidin-2,4-dionIIIc5-(4-Okso-4H-kromen-2-il metilen)-2-tiyokso-imidazolidin-4-onIIId3-Metil-5-(4-okso-4H-kromen-2-il metilen)-tiyazolidin-2,4-dionIIIe3-Etil-5-(4-okso-4H-kromen-2-il metilen)-tiyazolidin-2,4-dionIIIf1,3-Dimetil-5-(4-okso-4H-kromen-2-il metilen)-imidazolidin-2,4-dionIIIg3-Etil-5-(4-okso-4H-kromen-2-il metilen)-imidazolidin-2,4-dionIIIh3-Metil-2-(metiltiyo)-5-(4-okso-4H-kromen-2-il metilen)-imidazolidin-4-onIIIi3-Etil-2-(etiltiyo)-5-(4-okso-4H-kromen-2-il metilen)-imidazolidin-4-onIVa5-(4-Okso-4H-kromen-3-il metilen)-tiyazolidin-2,4-dionIVb5-(4-Okso-4H-kromen-3-il metilen)-imidazolidin-2,4-dionIVc5-(4-Okso-4H-kromen-3-il metilen)-2-tiyokso-imidazolidin-4-onIVd3-Metil-5-(4-okso-4H-kromen-3-il metilen)-tiyazolidin-2,4-dionIVe3-Etil-5-(4-okso-4H-kromen-3-il metilen)-tiyazolidin-2,4-dionIVf1,3-Dimetil-5-(4-okso-4H-kromen-3-il metilen)-imidazolidin-2,4-dionIVg3-Etil-5-(4-okso-4H-kromen-3-il metilen)-imidazolidin-2,4-dionIVh3-Metil-2-(metiltiyo)-5-(4-okso-4H-kromen-3-il metilen)-imidazolidin-4-onIVi3-Etil-2-(etiltiyo)-5-(4-okso-4H-kromen-3-il metilen)-imidazolidin-4-onAbstractA series of chromonyl-2,4-thiazolidinediones / imidazolidinediones / 2-thioxo-imidazolidine-4-ones (IIIa-i, IVa-i) was prepared by Knoevenagel reaction of 2,4-thiazolidinedione / 2,4-imidazolidinedione / 2-thioxo-imidazolidine-4-one (IIa-c) with 2/3-formyl chromone (Ia-b) and then alkylation with methyl / ethyl iodide . The structure of the synthesized 18 compounds was elucidated by IR, 1H NMR, Mass spectral data and elementary analysis findings and X-Ray analysis of compounds IVd, IVg and IVi was performed. The synthesized compounds were tested for their insulinotropic activities in INS-1 cells. Compounds IVb, IVc (at lower concentration; 1 μg/ml) were able to increase insulin release in the presence of 5.6 mmol/l glucose better than reference compound Glibenclamide. Chemical names of the synthesized compounds are given below;IIIa5-(4-Oxo-4H-chromen-2-yl methylene)-thiazolidine-2,4-dioneIIIb5-(4-Oxo-4H-chromen-2-yl methylene)-imidazolidine-2,4-dioneIIIc5-(4-Oxo-4H- chromen-2-yl methylene)-2-thioxo-imidazolidine-4-oneIIId3-Methyl-5-(4-oxo-4H- chromen-2-yl methylene)-thiazolidine-2,4-dioneIIIe3-Ethyl-5-(4-oxo-4H- chromen-2-yl methylene)-thiazolidine-2,4-dioneIIIf1,3-Dimethyl l-5-(4-oxo-4H- chromen-2-yl methylene)-imidazolidine-2,4-dioneIIIg3-Ethyl-5-(4-oxo-4H- chromen-2-yl methylene)-imidazolidine-2,4-dioneIIIh3-Methyl-2-(metiltiyo)-5-(4-oxo-4H- chromen-2-yl methylene)-imidazolidine-4-oneIIIi3-Ethyl-2-(ethylthio)-5-(4-oxo-4H- chromen-2-yl methylene)-imidazolidine-4-oneIVa5-(4-Oxo-4H- chromen-3-yl methylene)-thiazolidine-2,4-dioneIVb5-(4-Oxo-4H- chromen-3-yl methylene)-imidazolidine-2,4-dioneIVc5-(4-Oxo-4H- chromen-3-yl methylene)-2-tiyokso-imidazolidine-4-oneIVd3-Methyl-5-(4-oxo-4H- chromen-3-yl methylene)-thiazolidine-2,4-dioneIVe3-Ethyl-5-(4-oxo-4H- chromen-3-yl methylene)-thiazolidine-2,4-dioneIVf1,3-Dimethyl-5-(4-oxo-4H- chromen-3-yl methylene)-imidazolidine-2,4-dioneIVg3-Ethyl-5-(4-oxo-4H- chromen-3-yl methylene)-imidazolidine-2,4-dioneIVh3-Methyl-2-(methylthio)-5-(4-oxo-4H- chromen-3-yl methylene)-imidazolidine-4-oneIVi3-Ethyl-2-(ethylthio)-5-(4-oxo-4H-chromen-3-yl methylene)-imidazolidine-4-one
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    Yeni bazı biyolojik etkili flavonoid sentezleri üzerinde araştırmalar (B halkasında moleküler modifikasyon)
    (Fen Bilimleri Enstitüsü, 1994) Tunçbilek, Meral; Ertan, Rahmiye; Eczacılık
    In this study, synthesis of new flavonoid derivatives, which possess 1,4-dihydro- pyridine moiety at m- or p- positions of flavone ring were realised. For this purpose, totally seven steps reaction were carried out at the two different sections. Section 1 : Synthesis of 3' (or 4')-Formyl tlavones: The title flavonecarboxyaldehyde were obtained starting from o- (or p)-toluic acids by the six different reaction steps. All of these final compounds 3' (or 4')-fbrmylflavones and their intermediates 3' (or 4')-bromomethylflavones were synthesized as originally. Section 2: Synthesis of the 1,4-Dihydropyridine: This ring synthesis was realised starting from prepared flavonecarboxy aldehydes at the section 1, by the Hantzsch procedure. 24 New derivatives which are consisted different substituents at the third and fifth positions of 1,4-DHP and flavone rings were prepared. Their chemical names and code numbers are given below. 1m: Dimethyl 1,4-dihydro- 2,6-dimethyl- 4- [3'-(4H- 4-oxo- 1-benzopyran-2-yl) phenyll - 3,5- pyrldinedi- carboxylate 2m: Methyl ethyl 1,4-dlhydro- 2,6-dlmethyl- 4- [3M4H-4-oxo-1-benzopyran«2-yl)phenyl] -3,5- pyrldlnedl- carboxylate 3m: Methyl allyl 1,4-dlhydro- 2,6-dirnethyl-4-[3'-(4H-4-oxo-1-benzopyran-2-yDphenyl]-3,5-pyrldinedi- carboxylate 4m: Methyl t-butyl 1,4-dlhydro-2,6-dimethyl-4-[3'-(4H-4-oxo-1-benzopyran-2-yl)phenyl]-3,5-pyrldinedl- carboxylate 5m: Methyl 1,4-dlhydro-2,6-dlmethyl-3-phenyl carbamoyl-4-[3'-(4H-4-oxo-1-benzopyran-2-yl)phenylI-5- pyridinecarboxylate 6m: Diethyl 1,4-dihydro- 2,6-dlmethyl- 4- [3'- (4H- 4-oxo- 1- benzopyran- 2-yl) phenyl] -3,5- pyrldlnedl- carboxylate 7m: Ethyl allyl 1,4-dlhydro- 2,6- dlmethyl-4- [3'-(4H-4-oxo-1-benzopyran-2-yl) phenyl] -3,5- pyrldlnedl- carboxylate 8m: Ethyl t-butyl 1,4-dihydro- 2,6- dimethyl-4- [3'-{4H-4-oxö- 1-benzopyran-2-yl) phenyl]-3,5-pyrldlnedl- carboxylate 9m: Ethyl 1,4- dlhydro- 2,6- dlmethyl-4- [3'-(4H- 4- oxo-1 -benzopyran- 2- yl) phenyl]- 3,5- pyrldlnedl- carboxyiate acetanilld 10m: Diallyl 1,4-dlhydro- 2,6- dlmethyl-4- [3'-(4H-4-oxo- 1-benzopyran-2-yl) phenyl]-3,5-pyrldlnedl- carboxylate 11m: Dl t-butyl 1,4-dlhydro- 2,6- dlmethyl-4- [3'-(4H-4-oxo- 1 -benzopyran-2-yl) phenyl]-3,5-pyr!dlnedi- carboxylate190 12m: 1,4-dlhydro- 2,6- dimethy 1-4- [3'-(4H-4-oxo- l-benzopyran-2-yl) phenyl]-3,5-pyridine-N,N'-dlphenyl carboxamide Ipi Dimethyl 1,4-dihydro- 2,6-dimethyl- 4- [4'-(4H- 4-oxo- l-benzopyrarı-2-yl) phenyl] - 3,5- pyridinedi- carboxylate 2pt Methyl ethyl 1,4-dihydro- 2,6-dlmethyl- 4- [4'-(4H-4-oxo-1-benzopyran-2-yl)phenyl] -3,5- pyrldlnedi- carboxylate 3p: Methyl allyl 1,4-dihydro- 2,6-dlmethyl-4-[4'-(4H-4-oxo-1-benzopyran-2-yl)phenyl]-3,5-pyrldinedi- carboxylate 4pt Methyl t-butyl 1,4-dihydro-2,6-dlmethyl-4-[4'-(4H-4-oxo-l-benzopyran-2-yl)phenylI-3,5-pyr(dlnedI- carboxylate 5p: Methyl 1,4-dlhydro-2,6-dlmethyl-3-phenyl carbamoyl-4-[4'-(4H-4-oxo-1-benzopyran-2-yl)phenyl]-5- pyridinecarfaoxylate 6p: Diethyl 1,4-dlhydro- 2,6-dlmethyl- 4- [4'- (4H- 4-oxo- 1- benzopyran- 2-yl) phenyl] -3,5- pyridinedi- carboxylate 7px Ethyl allyl 1,4-dlhydro- 2,6- dlmethyl-4- [4'-(4H-4-oxo-1-benzopyran-2-yl) phenyl] -3,5- pyridinedi- carboxylate 8pî Ethyl t-butyl 1,4-dlhydro- 2,6- dimethyl-4- [4'-(4H-4-oxo- l-benzopyran-2-yl) phenyl]-3,5-pyrldlnedl- carboxylate 9p: Ethyl 1,4- dlhydro- 2,6- dlmethyl-4- [4'-(4H- 4- oxo-1 -benzopyran- 2- yl) phenyl]- 3,5- pyrldlnedl- carboxylate acetanilid 10p: Dlallyl 1,4-dlhydro- 2,6- dlmethyl-4- [4'-(4H-4-oxo- 1-benzopyran-2-yl) phenyl]-3,5-pyrldlnedl- carboxylate Up: Dl t-butyl 1,4-dlhydro- 2,6- dlmethyl-4- [4'-(4H-4-oxo- 1-benzopyran-2-yl) phenyll-3,5-pyrldlnedi- carboxylate 12ps 1,4-dlhydro- 2,6- dlmethyl-4- [4'-(4H-4-oxo- 1-benzopyran-2-yl) phenyl]-3^-pyrldlne-N,N'-diphenyl carboxamide The purities of the synthesized 28 compounds were checked some of their physicochemical parameters and chemical structures were elucidated by the UV, İR, HNMR, Mass spectral findings and elemental analyses. In addition X-Ray analyses of the compound 7p was realised and some of its structural parameters related with the biological activity was investigated. According to the obtained results; this compounds shows almost similiar conformation with the "Nifedipine" which is known as a prototype of the calcium channel blockers. Calcium channel blocker effect of the isomers 6m and 6p were investigated using "Nifedipine* as the reference compound. This pre-experiments results shows thar^ isomers 6m and 6p have comparable activity with the "Nifedipine".
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    Yeni bazı flavonoid türevlerinin sentezi, kimyasal yapılarının aydınlatılması ve monoamin oksidaz enzimleri üzerine etkilerinin araştırılması
    (Sağlık Bilimleri Enstitüsü, 2010) Evranos, Begüm; Ertan, Rahmiye
    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