Halogenated d-xylono-δ-lactams: synthesis and enzyme inhibition study. (30th January 2015)

• Record Type: Journal Article
• Authors: Bhuma, Naresh; Vangala, Madhuri; Nair, Roopa J.; Sabharwal, Sushma G.; Dhavale, Dilip D.
• Is Part Of: Carbohydrate research. Volume 402(2015)
• Page Start: 215
• Page End: 224
• Publication Date: 2015-01-30
• Subjects: Iminosugars -- Lactams -- Halogen -- Conformations -- Inhibitors; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2014.10.023
• Languages: English
• ISSNs: 0008-6215

Abstract

Graphical abstract: Halogenatedd -xylono-δ-lactams were synthesized from commercially availabled -glucose by using Corey–Link reaction and intra molecular Schmidt reaction as key steps. The glycosidase inhibition activity and conformational analysis by 1 H NMR of these compounds was studied. Highlights: The Corey–Link reaction was exploited with 3-keto-d -gluco derived sugar. New C-3 halogenatedd -xylono-δ-lactams were synthesized. The Schmidt–Boyer reaction was exploited for the synthesis ofd -xylono-δ-lactams. Glycosidase inhibitory activity of halogenatedd -xylono-δ-lactams was studied. Abstract: A concise synthesis of four C-3 fluoro/chloro-d -xylono-δ-lactams3/4 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/H2 O, in one pot, afforded lactams3/4 . Conformational aspect of δ-lactams was studied by the 1 H NMR spectroscopy. The halogenated δ-lactams3/4 showed no inhibition against different glycosidase enzymes.