Skip to Main content Skip to Navigation
Journal articles

Diastereoselective Synthesis of Potent Antimalarial Cis-β-lactam Agents

Abstract : Fifteen novel β-lactams bearing N-ethyl tert-butyl carbamate group 5a-o and fifteen N-(2-aminoethyl) β-lactams 6a-o were synthesized by [2+2] ketene-imine cycloaddition reaction (Staudinger). The cycloaddition reaction was found to be totally diastereoselective leading exclusively to theformation of cis-β-lactam derivatives. These newly synthesized β-lactams were evaluated for their antimalarial activity against p. falciparum K14 resistant strain and showed good to excellent EC 50 values. Of the thirty β-lactams tested, 5 h, 6a and 6c showed IC 50 < 20 µM while 5b, 5c, 5e, 5f, 5g, 5i, 5j, 6d, 6g and 6h exhibited IC 50 <50. Compounds 5c, 5h, and 5q-t were examined for their anticancer properties against K562 Leukemia cell line and 5s showed the best activity. Compounds 3a-j, 5a-o, 6a-o, were tested against S. aureus , E. coli, C. albicans and showed no activity below 125 µg/mL.
Complete list of metadatas

Cited literature [19 references]  Display  Hide  Download

https://hal-amu.archives-ouvertes.fr/hal-02392424
Contributor : Jean Michel Brunel <>
Submitted on : Wednesday, December 4, 2019 - 8:16:05 AM
Last modification on : Wednesday, August 19, 2020 - 12:08:17 PM
Long-term archiving on: : Thursday, March 5, 2020 - 12:40:56 PM

Files

IJPR_Volume 18_Issue 2_Pages 5...
Files produced by the author(s)

Identifiers

Collections

Citation

Aliasghar Jarrahpour, Maryam Rostami, Véronique Sinou, Christine Latour, Lamia Djouhri-Bouktab, et al.. Diastereoselective Synthesis of Potent Antimalarial Cis-β-lactam Agents. Iranian Journal of Pharmaceutical Research, 2019, 18 (2), pp.596-606. ⟨10.22037/ijpr.2017.2024⟩. ⟨hal-02392424⟩

Share

Metrics

Record views

141

Files downloads

14