Two novel proton transfer compounds (HAP) + (SAMAL) -and (HBI) + (SAMAL) -.H 2 O were obtained from (E)-4-oxo-4-(4-sulfamoylphenylamino)but-2-enoic acid (HSAMAL) and 2-aminopyridine (AP) or 1H-benzimidazole (BI), respectively. Copper(II) complexes of salts and of HSAMAL have also been prepared. They have been characterized by elemental, spectral, thermal analyses, magnetic measurement and molar conductivity. Human carbonic anhydrase isozymes (hCA I and hCA II) were purified from erythrocytes by using affinity chromatography as 84.40 and 188.71 fold, respectively. The inhibitory effects of synthesized compounds and acetazolamide (AAZ, control compound) on the hydratase and esterase activities of hCA isozymes have been studied as in vitro to find out their antiglaucoma potentials. The inhibition constant (K i ) values of the compounds were in the range of 0.18 ± 0.007 to 10.24 ± 0.014 µmol L -1 for hCA I, and 0.12 ± 0.004 to 130.11 ± 0.021 µmol L -1 for hCA II.

Bu çalışmada, ilk olarak sülfanilamit (sa) ve maleik anhidritin (mal) tepkimesinden (E)-3-(4-\ud sülfamoyilfenil)amino)büt-2-enoik asit (Hsamal) bileşiği sentezlenmiş ve sonra bu bileşiğin\ud 2-aminopiridin (ap) ile proton transfer tuzu (Hapsamal) hazırlanmıştır. Bu tuzun Fe(II), Co(II),\ud Ni(II) ve Zn(II) geçiş metal kompleksleri sentezlenmiştir. Proton transfer tuzlarının yapısı\ud elementel analiz, 1H-NMR, 13C-NMR, FT-IR, UV-Vis metotları ile aydınlatılmıştır. Amorf halde\ud elde edilen geçiş metal komplekslerinin yapıları ise elementel analiz, ICP-OES, FT-IR, UV-Vis,\ud manyetik duyarlılık ve molar iletkenlik sonuçları dikkate alınarak önerilmiştir. Ayrıca,\ud sentezlenen maddelerin insan eritrosit hCA I ve hCA II izoenzimleri üzerindeki inhibisyon\ud etkilerini belirlemek üzere in vitro çalışmalar yapılmıştır. Yeni sentezlenen maddelerin\ud izoenzimlerin esteraz aktivitesini inhibe ettiği tespit edilmiştir. Bu maddelerin inhibisyon\ud değerlerinin kontrol bileşiği asetazolamid (AAZ) değerleri ile kıyaslanabilir büyüklükte olduğu\ud tespit edilmiştir.In this study, first (E)-4-oxo-4-(4-sulfamoylphenylamino)but-2-enoic acid (Hsamal) have been\ud synthesized from the reaction between sulfanilamide (sa) and maleic anhydride (mal) and second,\ud proton transfer salt (Hapsamal) has been prepared from 2-aminopyridine (ap) and Hsamal. Four\ud transition metal complexes [Fe(II), Co(II), Ni(II) and Zn(II)] of the salt have also been synthesized. The\ud structure of proton transfer compounds have been proposed by using elemantal analysis, 1H-NMR,\ud 13C-NMR, FT-IR, UV-Vis techniques. The structure of amorphous metal complexes have been proposed\ud by using elemantal analysis, ICP-OES, FT-IR, UV-Vis, magnetic susceptibility and molar conductivity\ud techniques. In addition, in vitro studies have been performed to determine the inhibition effects of\ud synthesized compounds on human erythrocyte hCA I and hCA II isoenzymes. It has been observed that\ud synthesized compounds have affected esterase activities of hCA I and hCA II and the inhibition values\ud of these compounds are comparable with the inhibition values of control compound acetazolamide\ud (AAZ)

ÖZBu çalışmada, (E)-3-(4-sülfamoyilfenilkarbamoil)akrilik asit (1) ile 1H-benzimidazol (2) proton transfer tuzu (3) literatürde belirtildiği şekilde sentezlenmiştir. Bu tuzun Fe(II), Co(II), Ni(II) ve Zn(II) (4-7) geçiş metal kompleksleri sentezlenmiştir. Amorf halde elde edilen metal komplekslerinin yapıları elementel analiz, ICP-OES, FT-IR, UV-Vis, manyetik duyarlılık ve molar iletkenlik sonuçları ile önerilmiştir. Ayrıca, sentezlenen maddelerin insan eritrosit hCA I ve hCA II izoenzimleri üzerindeki inhibisyon etkilerini belirlemek üzere in vitro çalışmalar yapılmıştır. Yeni sentezlenen maddelerin izoenzimlerin esteraz aktivitesini inhibe ettiği tespit edilmiştir. Sentezlenen bileşiklerin inhibisyon değerlerinin kontrol bileşiği asetazolamid (AAZ) değerleri ile kıyaslanabilir büyüklüktedir.Anahtar Kelimeler: Sülfomoyil bileşikleri, 1H-benzimidazol, metal kompleksleri, karbonik anhidraz inhibisyonu.Synthesis and structural studies of proton transfer salt between benzimidazole and (E)-3-(4-sulfamoylphenylcarbamoyl)acrylic acid and their transition metal complexes, and investigation of their inhibition properties. ABSTRACTIn this study, proton transfer salt (3) was synthesized from (E)-3-(4-sulfamoylphenylcarbamoyl)acrylic acid (1) and 1H-benzimidazole (2), which is reported in literature. Four metal complexes [Fe(II), Co(II), Ni(II) and Zn(II), (4-7)] of the salt have also been synthesized. The structure of amorphous metal complexes have been proposed by using elemantal analysis, ICP-OES, FT-IR, UV-Vis, magnetic susceptibility and molar conductivity techniques. In addition, in vitro studies have been performed to determine the inhibition effects of synthesized compounds on human erythrocyte hCA I and hCA II isoenzymes. It has been observed that synthesized compounds have affected esterase activities of hCA I and hCA II and the inhibition values of these compounds are comparable with the inhibition values of control compound acetazolamide (AAZ).