title: Unsymmetrical 1,5-diaryl-3-oxo-1,4-pentadienyls and their evaluation as antiparasitic agents.
abstract: In this work the synthesis and antiparasitical activity of new 1,5-diaryl-3-oxo-1,4-pentadienyl derivatives are described. First, compounds 1a, 1b, 1c and 1d were prepared by acid-catalyzed aldol reaction between 2-butanone and benzaldehyde, anisaldehyde, p-N,N-dimethylaminobenzaldehyde and p-nitrobenzaldehyde. Reacting each of the methyl ketones 1a, 1b, 1c and 1d with the p-substituted benzaldehydes under basic-catalyzed aldol reaction, we further prepared compounds 2a-2p. All twenty compounds were evaluated for antiproliferative activity, particularly for promastigote of Leishmania amazonensis and epimastigote of Trypanosoma cruzi. All compounds showed good activity while nitro compounds 2i and 2k showed inhibition activity at a few μM.
authors.affiliation: LaBioMMi, Departamento de Química, Universidade Federal de São Carlos, CP 676, 13.565-905 São Carlos, SP, Brazil.
authors.forename: Zia
authors.initials: Z
authors.lastname: Ud Din
authors.affiliation: LaBioMMi, Departamento de Química, Universidade Federal de São Carlos, CP 676, 13.565-905 São Carlos, SP, Brazil.
authors.forename: Taicia Pacheco
authors.initials: TP
authors.lastname: Fill
authors.affiliation: LAQBO, Departamento de Química, Universidade Federal de São Carlos, CP 676, 13.565-905 São Carlos, SP, Brazil.
authors.forename: Francisco Favaro
authors.initials: FF
authors.lastname: de Assis
authors.affiliation: Laboratório de Inovação Tecnológica no Desenvolvimento de Fármacos e Cosméticos, Universidade Estadual de Maringá, Av. Colombo 5790, 87020-900, Bloco B-08 Maringá, PR, Brazil.
authors.forename: Danielle
authors.initials: D
authors.lastname: Lazarin-Bidóia
authors.affiliation: Laboratório de Inovação Tecnológica no Desenvolvimento de Fármacos e Cosméticos, Universidade Estadual de Maringá, Av. Colombo 5790, 87020-900, Bloco B-08 Maringá, PR, Brazil.
authors.forename: Vanessa
authors.initials: V
authors.lastname: Kaplum
authors.affiliation: Laboratório de Inovação Tecnológica no Desenvolvimento de Fármacos e Cosméticos, Universidade Estadual de Maringá, Av. Colombo 5790, 87020-900, Bloco B-08 Maringá, PR, Brazil.
authors.forename: Francielle Pelegrin
authors.initials: FP
authors.lastname: Garcia
authors.affiliation: Laboratório de Inovação Tecnológica no Desenvolvimento de Fármacos e Cosméticos, Universidade Estadual de Maringá, Av. Colombo 5790, 87020-900, Bloco B-08 Maringá, PR, Brazil.
authors.forename: Celso Vataru
authors.initials: CV
authors.lastname: Nakamura
authors.affiliation: LAQBO, Departamento de Química, Universidade Federal de São Carlos, CP 676, 13.565-905 São Carlos, SP, Brazil.
authors.forename: Kleber Thiago
authors.initials: KT
authors.lastname: de Oliveira
authors.affiliation: LaBioMMi, Departamento de Química, Universidade Federal de São Carlos, CP 676, 13.565-905 São Carlos, SP, Brazil. Electronic address: edinho@pq.cnpq.br.
authors.forename: Edson
authors.initials: E
authors.lastname: Rodrigues-Filho
mesh_terms: D000818:Animals; D000977:Antiparasitic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001547:Benzaldehydes / Q000737:chemistry; D002478:Cells, Cultured; D060326:Chemistry Techniques, Synthetic; D004353:Drug Evaluation, Preclinical / Q000379:methods; D007659:Ketones / Q000737:chemistry; D007891:Leishmania / Q000187:drug effects*; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D014344:Trypanocidal Agents / Q000737:chemistry / Q000494:pharmacology; D014349:Trypanosoma cruzi / Q000187:drug effects*
chemical_list: D000977:Antiparasitic Agents; D001547:Benzaldehydes; D007659:Ketones; D014344:Trypanocidal Agents; C024896:4-anisaldehyde; C032175:benzaldehyde
keywords: 1,5-Diaryl-3-oxo-1,4-pentadienyl; Chalcone analogues; Curcumin analogues; Dibenzalacetone; Leishmania; Trypanosoma