TY - JOUR
T1 - Stereoselective synthesis of sugar-based β-lactam derivatives
T2 - Docking studies and its biological evaluation
AU - Nagarajan, Subbiah
AU - Arjun, Pandian
AU - Raaman, Nanjian
AU - Shah, Anup
AU - Sobhia, M. Elizabeth
AU - Das, Thangamuthu Mohan
PY - 2012/4/8
Y1 - 2012/4/8
N2 - Highly diastereoselective synthesis of cis-β-lactams via [2+2] cycloaddition reactions of sugar-imine derivative possessing free hydroxyl groups at C-2 and C-3 positions and ketenes is described. exo-Approach of sugar-imine with ketene leads to the stereoselective formation of cis product and it is facilitated by hydrogen bonding interaction of C2-OH with carbonyl group of ketene. Docking studies show that these derivatives are having greater affinity towards PBP and it has been validated by in vivo studies. Among the different sugar-based azetidine-2-ones, compounds 6a and 6d were superior in activity to the commercial antibiotic tetracycline.
AB - Highly diastereoselective synthesis of cis-β-lactams via [2+2] cycloaddition reactions of sugar-imine derivative possessing free hydroxyl groups at C-2 and C-3 positions and ketenes is described. exo-Approach of sugar-imine with ketene leads to the stereoselective formation of cis product and it is facilitated by hydrogen bonding interaction of C2-OH with carbonyl group of ketene. Docking studies show that these derivatives are having greater affinity towards PBP and it has been validated by in vivo studies. Among the different sugar-based azetidine-2-ones, compounds 6a and 6d were superior in activity to the commercial antibiotic tetracycline.
KW - Antimicrobial studies
KW - Docking analysis
KW - Staudinger reaction
KW - Stereoselectivity
KW - Sugar-β-lactam
UR - http://www.scopus.com/inward/record.url?scp=84858700988&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2012.02.017
DO - 10.1016/j.tet.2012.02.017
M3 - Article
AN - SCOPUS:84858700988
SN - 0040-4020
VL - 68
SP - 3037
EP - 3045
JO - Tetrahedron
JF - Tetrahedron
IS - 14
ER -