Diastereoselective Synthesis of Potent Antimalarial Cis-β-lactam Agents

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JARRAHPOUR ALIASGHAR; ROSTAMI MARYAM; Sinou Veronique; Latour Christine; Djouhri Bouktab Lamia; Brunel Jean Michel

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Journal Paper

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Journal: Iranian Journal of Pharmaceutical Research Year:2019 | Volume:18 | Issue:2 Page(s): 596-606

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Title

Diastereoselective Synthesis of Potent Antimalarial Cis-β-lactam Agents

Author(s)

Keywords

N-(2-aminoethyl) β

-lactams;

tert-butyl carbamate;

2-Azetidinones;

P.falciparum;

Staudinger;

Antimalarial activity

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 EC50 values. Of the thirty β-lactams tested, 5 h, 6a and 6c showed IC50 < 20 μ M while 5b, 5c, 5e, 5f, 5g, 5i, 5j, 6d, 6g and 6h exhibited IC50 <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 μ g/mL.

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APA: Copy

JARRAHPOUR, ALIASGHAR, ROSTAMI, MARYAM, Sinou, Veronique, Latour, Christine, Djouhri Bouktab, Lamia, & Brunel, Jean Michel. (2019). Diastereoselective Synthesis of Potent Antimalarial Cis-β-lactam Agents. IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH (IJPR), 18(2), 596-606. SID. https://sid.ir/paper/289101/en

Vancouver: Copy

JARRAHPOUR ALIASGHAR, ROSTAMI MARYAM, Sinou Veronique, Latour Christine, Djouhri Bouktab Lamia, Brunel Jean Michel. Diastereoselective Synthesis of Potent Antimalarial Cis-β-lactam Agents. IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH (IJPR)[Internet]. 2019;18(2):596-606. Available from: https://sid.ir/paper/289101/en

IEEE: Copy

ALIASGHAR JARRAHPOUR, MARYAM ROSTAMI, Veronique Sinou, Christine Latour, Lamia Djouhri Bouktab, and Jean Michel Brunel, “Diastereoselective Synthesis of Potent Antimalarial Cis-β-lactam Agents,” IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH (IJPR), vol. 18, no. 2, pp. 596–606, 2019, [Online]. Available: https://sid.ir/paper/289101/en

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