Novel cephalosporin derivatives possessing a substituted cinnamoyl moiety at the 7 beta-position. Synthesis, structural characterization and antibacterial activity of 3-acetoxymethyl cephalosporin derivatives.
Twenty 3-acetoxymethyl cephalosporin derivatives, with various cinnamoyl (3-phenyl-2-propenoyl) substituted groups at the 7beta-position, were synthesized and evaluated for antibacterial activity in vitro. Some of these cephalosporin derivatives showed good selective activity against Gram-positive bacteria. Although substitution on the aromatic ring of cinnamoyl moiety generally reduced antimicrobial activity against Staphylococcus sp. and Enterococcus sp., a hydroxy group at the para position, and particularly ortho, para di-chloro substitution, improved the activity against methicillin resistant strains of Staphylococcus aureus (MRSA). Substitution on the double bond alpha position of the cinnamoyl moiety also affected the antimicrobial activity. A cyano group attached to this position increased activity against both negative coagulase Staphylococcus and Enterococcus sp. and extended the antibacterial spectrum towards Gram-negative bacteria.
Centro de Química Farmacéutica, Avenida 200 y 21, Siboney, Playa, CP 16042, La Habana, Cuba.
Miguel A
MA
López
Zalua
Z
Rodríguez
Maritza
M
González
Blanca
B
Tolón
Rizette
R
Avila
Ileana
I
González
Leonor
L
Garmendía
Taimirys
T
Mamposo
Ramón
R
Carrasco
Rolando
R
Pellón
Hermán
H
Vélez
Adamo
A
Fini
D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D002511:Cephalosporins / Q000737:chemistry* / Q000494:pharmacology; D002934:Cinnamates / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D008826:Microbial Sensitivity Tests; D013211:Staphylococcus aureus / Q000187:drug effects / Q000502:physiology; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D002511:Cephalosporins; D002934:Cinnamates