Abstract
Thirteen novel benzothiazole derivatives incorporating glycine, methionine, alanine, and phenylalanine were synthesised by facile acylation reactions through benzotriazole or DCC mediated reactions and their structures were identified by 1H-NMR, 13C-NMR, and FT-IR spectroscopic techniques and elemental analysis. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds was assessed against four human (h) isoforms, hCA I, hCA II, hCA V, and hCA XIII. Some of the synthesised compounds showed good in vitro carbonic anhydrase inhibitory properties, with inhibition constants in the micromolar level. The new amino acid benzothiazole conjugates found to be more effective against hCA V and hCA II inhibition. In vitro antioxidant activities of the novel compounds were determined by DPPH method. Most of the synthesised compounds showed moderate to low antioxidant activities compared to the control antioxidant compounds (BHA and α-tocopherol).
Highlights
Benzothiazole derivatives have been extensively studied in drug chemistry[1,2] and they exhibit diverse activities such as antitubercular[3], antimicrobial[4,5,6], antimalarial[7], anticonvulsant[8], antioxidant[9], antidiabetic[10], antitumor[11], carbonic anhydrase (CA)[12], and tryptase inhibitors[13]
Benzothiazole is an important scaffold for drug development, because it exhibits a broad spectrum of pharmacological activities[1,2]
In vitro antioxidant activities of the novel compounds were determined by DPPH method
Summary
Benzothiazole derivatives have been extensively studied in drug chemistry[1,2] and they exhibit diverse activities such as antitubercular[3], antimicrobial[4,5,6], antimalarial[7], anticonvulsant[8], antioxidant[9], antidiabetic[10], antitumor[11], carbonic anhydrase (CA)[12], and tryptase inhibitors[13]. CAs are a class of well-studied metalloenzymes that are widely distributed in all living organisms[20]. These enzymes (hCAs) are zinc-containing enzymes that catalyse the reversible hydration of carbon dioxide to bicarbonate and a proton (CO2 þ H2O!HCO3À þ Hþ). A similar interest is observed in synthesising effective antioxidants for food products and drugs
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