Synthesis, cytotoxicity, and antileishmanial activity of N,N'-disubstituted ethylenediamine and imidazolidine derivatives.
This paper describes the preparation of N,N'-disubstituted ethylenediamine and imidazolidine derivatives and their in vitro biological activities against Leishmania species. Of the nine synthesized compounds, five displayed a good activity in both L. amazonensis and L. major promastigotes. The compounds 1,2-Bis(p-methoxybenzyl) ethylenediamine (4) and 1,3-Bis(p-methoxybenzyl)imidazolidines (5) showed the best activity on intracellular amastigotes, with IC50 values of 2.0 and 9.4 microgram/mL, respectively. In addition, none of compounds were cytotoxic against mammalian cells. The leishmanicidal activity can be related with inhibition of polyamine synthesis and cellular penetration within biological membranes.
de Carvalho
Gustavo S G
GS
Departamento de Química, I.C.E., Universidade Federal de Juiz de Fora, Cidade Universitária, Juiz de Fora, Minas Gerais, Brasil. senradcarvalho@yahoo.com.br
Machado
Patrícia A
PA
de Paula
Daniela T S
DT
Coimbra
Elaine S
ES
da Silva
Adilson D
AD
D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D005029:Ethylenediamines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D048289:Imidazolidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007891:Leishmania / Q000187:drug effects; D018320:Leishmania major / Q000187:drug effects; D017737:Macrophages, Peritoneal / Q000166:cytology / Q000187:drug effects* / Q000469:parasitology; D051379:Mice; D008807:Mice, Inbred BALB C; D008956:Models, Chemical; D015394:Molecular Structure
D000981:Antiprotozoal Agents; D005029:Ethylenediamines; D048289:Imidazolidines; C031234:ethylenediamine