Piperazine derivatives of benzimidazole as potential anthelmintics. Part 1: Synthesis and activity of methyl-5-(4-substituted piperazin-1-yl)benzimidazole-2-carbamates.
A series of 5-(4-substituted piperazin-1-yl)-2-nitroanilines (4) and 5-(4-substituted piperazin-1-yl)benzimidazole-2-carbamates (6) has been synthesized starting from 5-chloro-2-nitroaniline (3) and N-monosubstituted piperazines. Catalytic reduction of 4 with Pd/C followed by treatment with 1,3-dicarbomethoxy-S-methylisothiourea yielded the corresponding methyl-5-(4-substituted piperazin-1-yl)benzimidazole-2-carbamates (6) which were for anthelmintic activity against experimental infections of Trichinella spiralis.
Sánchez-Alonso
R M
RM
Department of Organic Chemistry, University of Santiago de Compostela, Spain.
Raviña
E
E
Santana
L
L
García-Mera
G
G
Sanmartín
M
M
Baltar
P
P
D000818:Animals; D000871:Anthelmintics / Q000138:chemical synthesis*; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D002219:Carbamates / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D010879:Piperazines / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014234:Trichinella / Q000187:drug effects
D000871:Anthelmintics; D001562:Benzimidazoles; D002219:Carbamates; D010879:Piperazines