Structure of 5-amino-1,3,4-thiadiazole-2-sulfonamide, an inhibitor of the enzyme carbonic anhydrase

Abstract

In (E)-5-(1-phenyl-4-pyrazolylium)-2-pentenoate, the N...O distances lie in the range 8.557 (5)

Structural, vibrational, thermal and magnetic investigation of novel Co(II), Cu(II), Zn(II) and Hg(II) crystalline metal complexes with 2-amino-5-benzylmercapto-1,3,4-thiadiazole: a low weight model of protonated copolymer resin

“…As far as we know, information on the structural and spectroscopic behavior is also very scarce. Although some crystal thioether structures have been determined [6][7][8][9][10][11][12], there is no previous data of their metal complex structures determined by single crystal X-ray technique.…”

“…The 1,3,4-thiadiazole ring allows different substituents at positions 2 and 5. In the last years the structures and spectroscopic behavior of some crystalline 1,3,4-thiadiazole ligands containing -SO 2 NH 2 (sulfonamido) and -SH (thiol) groups at these positions (particularly position 2) and their metal complexes were determined in our laboratory [7][8][9][10][11][12][13][14][15]. The interactions of metal ions with these ligands have been widely studied [16][17][18][19][20][21][22].…”

Salts of 5-amino-2-sulfonamide-1,3,4-thiadiazole, a structural and analog of acetazolamide, show interesting carbonic anhydrase inhibitory properties, diuretic, and anticonvulsant action

“…In the first step, the deacetylation of acetazolamide (AZA) to give Hats was performed following the procedure reported in the literature 17 . This product was characterized by its FTIR spectrum resulting identical to that reported by Pedregosa et al 17,18 . In the second step, 100 mg of Hats (0.55 mmol) were suspended at room temperature in 50 mL of absolute ethanol (99.5%, Merck, Darmstadt, Germany) with permanent stirring.…”

“…The results obtained by our group with these sulfonamides indicated a notable increase in the CA inhibitory properties of metal complexes of sulfonamides such as acetazolamide or its deacetylated precursor, 5-amino-1,3,4-thiadiazole-2-sulfonamide (Hats) 23 . Furthermore, continuing our studies on unsubstituted heterocyclic sulfonamides and their metal complexes [17][18][19][20][21][22][23] , we started to study the role of new salts of Hats with regard to their biological activity. In this work, we report new salts of Hats with p-toluenesulfonic acid, methylsulfonic acid, and the hydrochloride monohydrate salts.…”

“…Despite the development of a rapid tolerance consisting in diminished therapeutic efficacy after the initial response of the patients, acetazolamide is still used in combination therapy with other antiepileptic drugs or inrefractory epilepsies 1 . We have obtained and determined the crystal structures of sulfonamides incorporating the 1,3,4-thiadiazole ring [17][18][19][20][21][22][23] . The results obtained by our group with these sulfonamides indicated a notable increase in the CA inhibitory properties of metal complexes of sulfonamides such as acetazolamide or its deacetylated precursor, 5-amino-1,3,4-thiadiazole-2-sulfonamide (Hats) 23 .…”