Synthesis and bioactivity studies on new 4-(3-(4-Substitutedphenyl)-3a,4-dihydro-3H-indeno[1,2-c]pyrazol-2-yl) benzenesulfonamides


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GÜL H. İ., TUĞRAK M., Sakagami H., TASLIMI P., GÜLÇİN İ., SUPURAN C. T.

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, vol.31, no.6, pp.1619-1624, 2016 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 31 Issue: 6
  • Publication Date: 2016
  • Doi Number: 10.3109/14756366.2016.1160077
  • Journal Name: JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1619-1624
  • Keywords: Benzenesulfonamide, carbonic anhydrase/enzyme inhibition, cytotoxicity, indane, pyrazole, tumor selectivity, CARBONIC-ANHYDRASE INHIBITORS, BIOLOGICAL EVALUATION, ISOENZYMES INHIBITORS, ANTICANCER AGENTS, PYRAZOLINE DERIVATIVES, ANTIMICROBIAL AGENTS, CYTOTOXIC ACTIVITIES, CELL-LINES, ISOFORMS I, SULFONAMIDES
  • Ataturk University Affiliated: Yes

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.