title: Halogenated D-xylono-δ-lactams: synthesis and enzyme inhibition study.
abstract: A concise synthesis of four C-3 fluoro/chloro-D-xylono-δ-lactams 3/4 has been reported. The methodology involves Corey-Link approach with suitably protected 3-oxo-D-gluco-furanose to introduce F/Cl as well as ester/amide functionalities at C-3 of glucose. In next steps, 5,6-O-isopropylidene group was converted to the 5-azido xylosugars that on opening of 1,2-acetonide group, and intramolecular Schmidt-Boyer reaction with TFA/H2O, in one pot, afforded lactams 3/4. Conformational aspect of δ-lactams was studied by the 1H NMR spectroscopy. The halogenated δ-lactams 3/4 showed no inhibition against different glycosidase enzymes.
authors.affiliation: Department of Chemistry, Garware Research Centre, University of Pune, Pune 411007, India.
authors.forename: Naresh
authors.initials: N
authors.lastname: Bhuma
authors.affiliation: Department of Chemistry, Garware Research Centre, University of Pune, Pune 411007, India.
authors.forename: Madhuri
authors.initials: M
authors.lastname: Vangala
authors.affiliation: Division of Biochemistry, Department of Chemistry, University of Pune, Pune 411007, India.
authors.forename: Roopa J
authors.initials: RJ
authors.lastname: Nair
authors.affiliation: Division of Biochemistry, Department of Chemistry, University of Pune, Pune 411007, India.
authors.forename: Sushma G
authors.initials: SG
authors.lastname: Sabharwal
authors.affiliation: Department of Chemistry, Garware Research Centre, University of Pune, Pune 411007, India. Electronic address: ddd@chem.unipune.ac.in.
authors.forename: Dilip D
authors.initials: DD
authors.lastname: Dhavale
mesh_terms: D001386:Azides / Q000737:chemistry; D002236:Carbohydrate Conformation; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005663:Furans / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D054879:Halogenation; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D001386:Azides; D004791:Enzyme Inhibitors; D005663:Furans; D007769:Lactams; D006026:Glycoside Hydrolases; D005947:Glucose
keywords: Conformations; Halogen; Iminosugars; Inhibitors; Lactams