Preparation of Two Maleic Acid Sulfonamide Salts and Their Copper(II) Complexes and Antiglaucoma Activity Studies

Abstract

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.

Spray coating thin polymeric sensor films for Au3+

“…In general, chemical shift of sulfonamide N H proton about 6–8 ppm and protons attached to nitrogen atoms may be exchangeable . For free PSS‐Rho4 , there was no chemical shift of the sulfonamine N H protons, which might be attributed to the quick exchange with the residual water in the deuteration solution and increased intermolecular hydrogen bonding of polymer, whereas in the presence of Au 3+ ions, it was appeared and shifted downfield (9.62 ppm). In addition, the chemical shifts of all the protons also showed distinct downfield changes and peak broadening, especially the aromatic protons, which may be due to Au 3+ complexation and conformational organization.…”

Benzi̇mi̇dazol İle (E)-3-(4-Sülfamoyi̇lfeni̇lkarbamoi̇l)akri̇li̇k Asi̇ti̇n Proton Transfer Tuzunun Sentezi̇, Metal Kompleksleri̇ni̇n Hazirlanmasi Ve İnhi̇bi̇syon Özelli̇kleri̇ni̇n İncelenmesi̇

“…Bu yapıların önerilmesinde, yukarıda tartışılan deneysel sonuçlar, yük denkliği ve daha önce yapılmış benzer çalışmalar dikkate alınmıştır [18,19,[26][27][28][29][30]. …”

“…Daha sonra bu asitin 1H-benzimidazol (2) [17] ile tepkimesinden proton transfer tuzu bileşiği (1H-benzimidazol-3-yum (E)-4-okso-4-((4-sülfamoyilfenil)amino)büt-2-enoat, 3) hazırlanmıştır [18,19]. Bu tuzun Fe(II), Co(II), Ni(II) ve Zn(II) (4-7) ile verdiği komplekslerin yapıları aydınlatılmaya çalışılmıştır.…”

Synthesis and Structural Studies of Proton Transfer Salt Between Benzimidazole and (E)-4-oxo-4-(4-sulfamoylphenylamino)but-2-enoic Acid and Their Transition Metal Complexes, and Investigation of Inhibition Properties on hCAI and hCA II Isoenzymes

“…Elde edilen kompleks bileşiklerin bazı fiziksel özellikleri Tablo 1'de verilmiştir. [Yenikaya et al 2016].…”

“…Bu çalışmada önce sülfanilamit (sa) ile maleik anhidrit (mal) bileşiğinin tepkimesi sonucunda sülfamoyil grubu içeren amid bileşiği literatürdeki gibi sentezlenmiştir [(E)-4-okso-4-(4sülfamoyilfenil)amino)büt-2-enoik asit, Hsamal] [Bergmann ve Schapiro 1942]. Daha sonra Hsamal ile 2-aminopiridin (ap) tepkimesinden proton transfer tuzu bileşiği Hapsamal [(E)-2aminopridinyum 4-okso-4-(4-sülfamoyilfenilamino) büt-2-enoat] hazırlanmıştır [Demirel 2013;Yenikaya et al 2016]. Bu tuzun Fe(II), Co(II), Ni(II) ve Zn(II) ile verdiği komplekslerin yapıları aydınlatılmaya çalışılmıştır.…”