Novel sulfamate derivatives of menthol: Synthesis, characterization, and cholinesterases and carbonic anhydrase enzymes inhibition properties

Abstract

Sulfamates have a large spectrum of biological activities including enzyme inhibition. Eight sulfamates derived from menthol (2a-h) were synthesized. Also, in the other section of this study, novel sulfamate derivatives of menthol were tested against some metabolic enzymes including acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and carbonic anhydrase I and II enzymes (hCAs I and II). The newly synthesized novel menthol sulfamate and menthol carbonyl sulfamate derivatives showed K-i values in the range of 34.37 +/- 8.17 to 53.40 +/- 10.61 nM against hCA I, 12.91 +/- 4.57 to 38.67 +/- 6.22 nM against hCA II, 111.17 +/- 52.36 to 522.86 +/- 120.08 nM against AChE, and 50.01 +/- 11.73 to 109.63 +/- 50.08 nM against BChE. As a result, the novel menthol sulfamate and menthol carbonyl sulfamate derivatives can be promising Alzheimer's disease drug candidates and novel hCA I and hCA II enzymes inhibitors.