Bicyclic hybrid sugars as glycosidase inhibitors: synthesis and comparative study of inhibitory activities of fused oxa-oxa, oxa-aza, and oxa-carbasugar hybrid molecules.
A few bicyclic hybrid sugar molecules comprising of oxa-aza, oxa-oxa, and oxa-carbasugar fused skeletons were designed and synthesized from C-2 acetoxyglucal involving Ferrier rearrangement, Grignard addition, and ring-closing metathesis as key steps. The inhibitory activities of the synthesized molecules were tested against commercially available enzymes, which revealed the sugar-piperidine and sugar-pyran hybrids as potent and selective inhibitors.
Department of Chemistry, Indian Institute of Technology , Kanpur, Uttar Pradesh 208016, India.
Alafia A
AA
Ansari
Parasuraman
P
Rajasekaran
M Musawwer
MM
Khan
Yashwant D
YD
Vankar
D001372:Aza Compounds / Q000737:chemistry* / Q000494:pharmacology*; D054329:Carbasugars / Q000138:chemical synthesis* / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry* / Q000494:pharmacology*; D010880:Piperidines / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*
D001372:Aza Compounds; D054329:Carbasugars; D004791:Enzyme Inhibitors; D010087:Oxides; D010880:Piperidines; D011714:Pyrans; C032727:piperidine; D006026:Glycoside Hydrolases