Molecular electrostatic potential-anthelmintic activity relationships of 5H-mebendazole and some related heterocyclic carbamates.
5H-Mebendazole and some related heterocyclic methyl carbamates were synthesized and their anthelmintic activity against Caenorhabditis elegans was determined. In order to study the influence of the heteroaromatic region with regard to the carbamate moiety on biological activity, the molecular electrostatic potentials (MEP) of all structures were calculated and a structure-activity relationship (SAR) was established. The electrostatic pattern of activity includes two minima of the carbamate moiety, a third heterocyclic minimum, and a pi-electronic region.
Cativiela
C
C
Departamento de Química Orgánica, Universidad de Zaragoza, Spain.
Garcia
J I
JI
Marin
A
A
Valls
N
N
Elguero
J
J
D000818:Animals; D000871:Anthelmintics; D002219:Carbamates / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004563:Electrochemistry; D008463:Mebendazole / Q000031:analogs & derivatives / Q000494:pharmacology*; D008968:Molecular Conformation; D009348:Nematoda / Q000187:drug effects; D013329:Structure-Activity Relationship
D000871:Anthelmintics; D002219:Carbamates; D008463:Mebendazole