Stereoselective synthesis of sugar-based β-lactam derivatives: Docking studies and its biological evaluation

Subbiah Nagarajan, Pandian Arjun, Nanjian Raaman, Anup Shah, M. Elizabeth Sobhia, Thangamuthu Mohan Das

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17 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3037-3045
Number of pages9
JournalTetrahedron
Volume68
Issue number14
DOIs
Publication statusPublished - 8 Apr 2012
Externally publishedYes

Keywords

  • Antimicrobial studies
  • Docking analysis
  • Staudinger reaction
  • Stereoselectivity
  • Sugar-β-lactam

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