title: Synthesis and bioactivity studies on new 4-(3-(4-Substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides.
abstract: A series of new 4-(3-(4-substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides (7-12) was synthesized starting from 2-(4-substitutedbenzylidene)-2,3-dihydro-1H-inden-1-one (1-6) and 4-hydrazinobenzenesulfonamide. The substituted benzaldehydes from which the key intermediate was prepared by introducing 2- or 4-substituents such as fluorine, hydroxy, methoxy, or the 3,4,5-trimethoxy moieties. The compounds were tested for their cytotoxicity, tumor-specificity and potential as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. The 3,4,5-trimethoxy and the 4-hydroxy derivatives showed interesting cytotoxic activities, which may be crucial for further anti-tumor activity studies, whereas some of these sulfonamides strongly inhibited both human (h) cytosolic isoforms hCA I and II.
authors.affiliation: a Department of Pharmaceutical Chemistry , Faculty of Pharmacy, Ataturk University , Erzurum , Turkey .
authors.forename: Halise Inci
authors.initials: HI
authors.lastname: Gul
authors.affiliation: a Department of Pharmaceutical Chemistry , Faculty of Pharmacy, Ataturk University , Erzurum , Turkey .
authors.forename: Mehtap
authors.initials: M
authors.lastname: Tugrak
authors.affiliation: b Division of Pharmacology , Meikai University School of Dentistry , Sakado , Saitama , Japan .
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Sakagami
authors.affiliation: c Ataturk University, Faculty of Science, Department of Chemistry , Erzurum , Turkey .
authors.forename: Parham
authors.initials: P
authors.lastname: Taslimi
authors.affiliation: c Ataturk University, Faculty of Science, Department of Chemistry , Erzurum , Turkey .|d College of Science, Department of Zoology, King Saud University , Riyadh , Saudi Arabia , and.
authors.forename: Ilhami
authors.initials: I
authors.lastname: Gulcin
authors.affiliation: e Neurofarba Department and Laboratorio di Chimica Bioinorganica , Università degli Studi di Firenze , Sesto Fiorentino , Italy.
authors.forename: Claudiu T
authors.initials: CT
authors.lastname: Supuran
mesh_terms: D066241:Carbon-13 Magnetic Resonance Spectroscopy; D045744:Cell Line, Tumor; D006801:Humans; D020128:Inhibitory Concentration 50; D066244:Proton Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000494:pharmacology*; D000096926:Benzenesulfonamides
chemical_list: D013449:Sulfonamides; D000096926:Benzenesulfonamides
keywords: Benzenesulfonamide; carbonic anhydrase/enzyme inhibition; cytotoxicity; indane; pyrazole; tumor selectivity