3 years ago

Synthesis and antimicrobial/antimalarial activities of novel naphthalimido trans -β-lactam derivatives

Aliasghar Jarrahpour, Edward Turos, Taibi Ben Hadda, Christine Latour, Yahia Mabkhot, Veronique Sinou, Jean Michel Brunel, Javad Ameri Rad, Hsaine Zgou

Abstract

This paper describes for the first time the synthesis and microbiological assessment of some new β-lactam derivatives containing a 1,8-naphthalimide functional group. These compounds were obtained through a [2 + 2] cyclocondensation (Staudinger reaction) of a ketene derived from 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl) acetic acid (Alrestatin) and various N-arylimines. The reaction was totally diastereoselective leading exclusively to the formation of trans-β-lactam adducts 3a–l, which were characterized by FT-Infra Red, 1H NMR, 13C NMR, mass spectrometry, elemental analyses, and X-ray crystallography, and then individually evaluated for antibacterial and antimalarial activities. Two of the β-lactams, 3c and 3l, afforded IC50 values of 3 and 5 µM, respectively, against Plasmodium falciparum K1 resistant strain.

Publisher URL: https://link.springer.com/article/10.1007/s00044-017-1920-z

DOI: 10.1007/s00044-017-1920-z

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