An efficient method for the synthesis of some chlorinated and heteroatom rich triazole-linked β-lactam glycoconjugates

The synthetic utility of chlorinated bicyclic C-fused tetrahydrofuro[3,2-c] azetidin-2-ones synthesized in our laboratory by Cu(I)-catalyzed halogen atom transfer radical cyclization (ATRC) has been illustrated through the synthesis of some novel p-lactam glycoconjugates. The chlorine atom of the chloromethyl side chain of the bicyclic C-fused tetrahydrofuro[3,2-c] azetidin-2-ones was subjected to nucleophilic substitution with azide group followed by Cu(l)-catalyzed azide-alkyne click reaction (CuAAC) with propargyl glycosides to generate the desirous beta-lactam glycoconjugates. A sequential optimization of the reaction procedure for CuAAC was carried out to obtain an efficient catalyst system to achieve beta-lactam glycoconjugates in good yields. The beta-lactam glycoconjugates are the compounds of interesting architecture and structurally suitable for bioactivity evaluation. Therefore, these beta-lactam glycoconjugates were screened for in vitro antibacterial activity. Additionally, a representative beta-lactam glycoconjugate was also tested for biocompatibility and cytotoxic activity against L929 cancer cell lines. (C) 2016 Elsevier Ltd. All rights reserved.