Synthesis of limonene beta-amino alcohol derivatives in support of new antileishmanial therapies.
A series of seven limonene beta-amino alcohol derivatives has been regioselectively synthesised in moderate to good yields. Two of these compounds were found to be significantly effective against in vitro cultures of the Leishmania (Viannia) braziliensis promastigote form in the micromolar range. The activities found for 3b and 3f were about 100-fold more potent than the standard drug, Pentamidine, in the same test, while limonene did not display any activity. This is the first report of antileishmanial activity by limonene beta-amino alcohol derivatives.
Ferrarini
Stela R
SR
Laboratório de Síntese Orgânica Medicinal, Universidade Federal do Rio Grande do Sul, Porto Alegre, RS, Brasil.
Graebin
Cedric S
CS
Limberger
Jones
J
Canto
Rômulo F S
RF
Dias
Daiane O
DO
Rosa
Ricardo G da
RG
Madeira
Maria de Fátima
Mde F
Eifler-Lima
Vera L
VL
D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D053138:Cyclohexenes / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D007892:Leishmania braziliensis / Q000187:drug effects*; D000077222:Limonene; D051379:Mice; D015394:Molecular Structure; D021261:Parasitic Sensitivity Tests; D013329:Structure-Activity Relationship; D013729:Terpenes / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity
D000605:Amino Alcohols; D000981:Antiprotozoal Agents; D053138:Cyclohexenes; D013729:Terpenes; D000077222:Limonene