Benzotriazole-Based Strategies Toward Peptidomimetics, Conjugates, and Other Peptide Derivatives

Albers, Thomas; Watkins, Davita L.; Gameiro, Armanda Formigao; Povstyanoy, Vyacheslav M.; Povstyanoy, Mykhaylo V.; Lebedyeva, Iryna

doi:10.1007/7081_2015_182

Cited by 2 publications

(1 citation statement)

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“…The syntheses of novel homosulphonamide and 4-aminoethylsulphonamide-amino acid conjugates prepared in this study are shown in Scheme 1. Since N-acylbenzotriazoles have been successfully utilised in many acylation reaction for the preparation N-, O-, S-, and C-substituted amino acid or peptides [31][32][33][34][35][36][37][38][39][40] , we chose the benzotriazole-mediated methodology to synthesise the targeted amino acid-sulphonamide conjugates. Compounds 1-12 were prepared through a facile benzotriazole mediated acylation reactions in one step (Scheme 1) at 70 C under microwave irradiation for 30 min, in dry dichloromethane as solvent, whereas compounds 13-24 were prepared using the same method except the presence of triethylamine in the reaction mixture, in order to remove hydrogen chloride from the homosulphonamide .…”

Section: Synthesis and Characterisation Of The New Amino Acid-sulphonmentioning

confidence: 99%

Synthesis and human carbonic anhydrase I, II, VA, and XII inhibition with novel amino acid–sulphonamide conjugates

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et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of amino acid-sulphonamide conjugates was prepared through benzotriazole mediated coupling reactions and characterised by 1 H-NMR, 13 C-NMR, MS, and FTIR spectroscopic techniques as well as elemental analysis. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds was determined against four human (h) isoforms, hCA I, hCA II, hCA VA, and hCA XII. Most of the synthesised compounds showed effective in vitro CA inhibitory properties. The new amino acid-sulphonamide conjugates showed potent inhibitory activity against hCA II, some of them at subnanomolar levels, exhibiting more effective inhibitory activity compared to the standard drug acetazolamide. Some of these sulphonamides were also found to be effective inhibitors of hCA I, hCA VA, and hCA XII, with activity from the low to high nanomolar range.

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