title: Improved synthesis of seven aromatic Baylis-Hillman adducts (BHA): evaluation against Artemia salina Leach. and Leishmania chagasi.
abstract: We described a very efficient procedure to prepare seven aromatic compounds (1-7), a new class of antileishmanial substances, through Baylis-Hillman reaction (BHR). With one, all the Baylis-Hillman adducts were prepared in quantitative yields by reaction of the corresponding aromatic aldehydes in acrylonitrile at 0 degrees C in only 10-40min reaction time. We present our results about the toxicities of these compounds evaluated on the microcrustaceous Artemia salina Leach. and against promastigote Leishmania chagasi. All substances evaluated in this work have showed high bioactivity. The 3-hydroxy-2-methylene-3-(4-bromopheny)propanenitrile (4) (LC(50)=30.9 microg/mL on A. salina; IC(50)=25.2 microM on L. chagasi) was the most active compound evaluated on A. salina Leach. and on promastigote L. chagasi. The 2-[hydroxy(pyridin-4-yl)methyl]acrylonitrile (7) (LC(50)=30.9 microg/mL on A. salina Leach.; IC(50)=4.8 microg/mL on L. chagasi) was also a very active substance evaluated in this work on promastigote L. chagasi.
authors.affiliation: Departamento de Química, Universidade Federal da Paraíba, Campus I, 58059-900 João Pessoa, PB, Brazil.
authors.forename: Ticiano P
authors.initials: TP
authors.lastname: Barbosa
authors.forename: Cláudio G L
authors.initials: CG
authors.lastname: Junior
authors.forename: Fábio P L
authors.initials: FP
authors.lastname: Silva
authors.forename: Horacimone M
authors.initials: HM
authors.lastname: Lopes
authors.forename: Lucas R F
authors.initials: LR
authors.lastname: Figueiredo
authors.forename: Suervy C O
authors.initials: SC
authors.lastname: Sousa
authors.forename: Guilherme N
authors.initials: GN
authors.lastname: Batista
authors.forename: Thiago G
authors.initials: TG
authors.lastname: da Silva
authors.forename: Tania M S
authors.initials: TM
authors.lastname: Silva
authors.forename: Márcia R
authors.initials: MR
authors.lastname: de Oliveira
authors.forename: Mário L A A
authors.initials: ML
authors.lastname: Vasconcellos
mesh_terms: D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D001156:Artemia / Q000187:drug effects*; D020128:Inhibitory Concentration 50; D007891:Leishmania / Q000187:drug effects*; D009930:Organic Chemicals / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity
chemical_list: D000981:Antiprotozoal Agents; D009930:Organic Chemicals