Details

Autor(en) / Beteiligte

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

Titel

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

Ist Teil von

• Medicinal chemistry research, 2017-10, Vol.26 (10), p.2235-2242

Ort / Verlag

New York: Springer US

Erscheinungsjahr

2017

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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, 1 H NMR, 13 C 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 IC 50 values of 3 and 5 µM, respectively, against Plasmodium falciparum K1 resistant strain.