2. Academic Validation
  3. Synthesis and carbonic anhydrase inhibition studies of sulfonamide based indole-1,2,3-triazole chalcone hybrids

Synthesis and carbonic anhydrase inhibition studies of sulfonamide based indole-1,2,3-triazole chalcone hybrids

  • Bioorg Chem. 2020 Jun;99:103839. doi: 10.1016/j.bioorg.2020.103839.
Priti Singh 1,  Baijayantimala Swain 1,  Pavitra S Thacker 1,  Dilep Kumar Sigalapalli 1,  P Purnachander Yadav 1,  Andrea Angeli 2,  Claudiu T Supuran 3,  Mohammed Arifuddin 4
Affiliations

Affiliations

  • 1 Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Balanagar, Hyderabad 500037, India.
  • 2 UniversitàdegliStudi di Firenze, Neurofarba Dept., Sezione di ScienzeFarmaceutiche e Nutraceutiche, Via Ugo Schiff 6, 50019 Sesto Fiorentino, Florence, Italy.
  • 3 UniversitàdegliStudi di Firenze, Neurofarba Dept., Sezione di ScienzeFarmaceutiche e Nutraceutiche, Via Ugo Schiff 6, 50019 Sesto Fiorentino, Florence, Italy. Electronic address: claudiu.supuran@unifi.it.
  • 4 Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Balanagar, Hyderabad 500037, India. Electronic address: arifabib@gmail.com.
PMID: 32289586 DOI: 10.1016/j.bioorg.2020.103839
Abstract

Sulfonamide is one of the most promising classes of classical Carbonic Anhydrase (CA, EC 4.2.1.1) inhibitors. A novel series of indolylchalcones incorporating benzenesulfonamide-1,2,3-triazole (6a-q) has been synthesized by Click Chemistry reaction and investigated for hCA inhibitory activity against a panel of human carbonic anhydrases (hCAs). Most of these newly synthesized compounds exhibited interesting inhibition constants, in the nanomolar range, with some derivatives being more potent than the standard drug acetazolamide (AAZ) on hCA I isoform. Among the tested compounds, the compounds 6d (18.8 nM), 6q (38.3 nM) and 6e (50.4 nM) were 13, 6 and 5 times more potent than AAZ against hCA I isoform, respectively. Compounds 6o, 6m and 6f efficiently inhibited isoform hCA XII, with KIs in the range of 10-41.9 nM. Several compounds were also active against isoforms hCA II and hCA IX, with KIs under 100 nM. These indolylchalcone-benzenesulfonamide-1,2,3-triazole hybrids may be considered as potential leads for hCA I-selective inhibitors.

Keywords

Acetazolamide; Carbonic anhydrase; Indolylchalcone- benzenesulfonamide-1, 2, 3-triazole hybrids; Knoevenagel condensation; Selective hCA I inhibition.

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