Tetrahedron p. 7982 - 7991 (2016)
Update date:2022-09-26
Topics:
Dawra, Nisha
Ram, Ram N.
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 β-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(I)-catalyzed azide-alkyne click reaction (CuAAC) with propargyl glycosides to generate the desirous β-lactam glycoconjugates. A sequential optimization of the reaction procedure for CuAAC was carried out to obtain an efficient catalyst system to achieve β-lactam glycoconjugates in good yields. The β-lactam glycoconjugates are the compounds of interesting architecture and structurally suitable for bioactivity evaluation. Therefore, these β-lactam glycoconjugates were screened for in vitro antibacterial activity. Additionally, a representative β-lactam glycoconjugate was also tested for biocompatibility and cytotoxic activity against L929 cancer cell lines.
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