Studies on the trypanocidal activity of semi-synthetic pyran[b-4,3]naphtho[1,2-d]imidazoles from beta-lapachone.
We synthesized new naphthoimidazoles from beta-lapachone with an aromatic moiety linked to the imidazole ring, using phenylic and heterocyclic aldehydes. The most active compound against Trypanosoma cruzi had a p-methyl group linked to the phenyl ring, presenting an EC(50) value of 15.5 +/- 2.9 microM. No reliable correlation could be established with the biological activity and the structure of in the phenylic series. For the heterocyclic series, activity was associated with a three bond-distance from nitrogen to the imidazole ring, in accordance with our previous work.
De Moura
Kelly C G
KC
Núcleo de Pesquisas em Produtos Naturais, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro 21944-970, Brazil.
Salomão
Kelly
K
Menna-Barreto
Rubem F S
RF
Emery
Flávio S
FS
Pinto
Maria do Carmo F R
Mdo C
Pinto
Antônio V
AV
de Castro
Solange L
SL
D000818:Animals; D000890:Anti-Infective Agents / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D051379:Mice / Q000469:parasitology; D008958:Models, Molecular; D008968:Molecular Conformation; D009285:Naphthoquinones / Q000737:chemistry*; D018512:Parasitemia / Q000188:drug therapy*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014344:Trypanocidal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D014349:Trypanosoma cruzi / Q000187:drug effects*
D000890:Anti-Infective Agents; D007093:Imidazoles; D009285:Naphthoquinones; D011714:Pyrans; D014344:Trypanocidal Agents; C014638:beta-lapachone