title: Efficient synthesis of 16 aromatic Morita-Baylis-Hillman adducts: Biological evaluation on Leishmania amazonensis and Leishmania chagasi.
abstract: Sixteen aromatic Morita-Baylis-Hillman adducts (MBHA) 1-16 were efficiently synthesized in a one step Morita-Baylis-Hillman reaction (MBHR) involving commercial aldehydes with methyl acrylate or acrylonitrile (81-100% yields) without the formation of side products on DABCO catalysis and at low temperature (0°C). The toxicities of these compounds were assessed against promastigote form of Leishmania amazonensis and Leishmania chagasi. The low synthetic cost of these MBHA, green synthetic protocols, easy one-step synthesis from commercially available and cheap reagents as well as the very good antileishmanial activity obtained for 14 and 16 (IC₅₀ values of 6.88μgmL⁻¹ and 11.06μgmL⁻¹ respectively on L. amazonensis; 9.58μgmL⁻¹ and 14.34μgmL⁻¹ respectively on L. chagasi) indicates that these MBHA can be a novel and promising class of anti-parasitic compounds.
authors.affiliation: Departamento de Química, Universidade Federal da Paraíba, João Pessoa, PB, Brazil.
authors.forename: Cláudio G L
authors.initials: CG
authors.lastname: Junior
authors.forename: Priscila A C
authors.initials: PA
authors.lastname: de Assis
authors.forename: Fábio P L
authors.initials: FP
authors.lastname: Silva
authors.forename: Suervy C O
authors.initials: SC
authors.lastname: Sousa
authors.forename: Natália G
authors.initials: NG
authors.lastname: de Andrade
authors.forename: Ticiano P
authors.initials: TP
authors.lastname: Barbosa
authors.forename: Patrícia L N
authors.initials: PL
authors.lastname: Nerís
authors.forename: Luiz V G
authors.initials: LV
authors.lastname: Segundo
authors.forename: Italo C
authors.initials: IC
authors.lastname: Anjos
authors.forename: Gabriel A U
authors.initials: GA
authors.lastname: Carvalho
authors.forename: Gerd B
authors.initials: GB
authors.lastname: Rocha
authors.forename: Márcia R
authors.initials: MR
authors.lastname: Oliveira
authors.forename: Mário L A A
authors.initials: ML
authors.lastname: Vasconcellos
mesh_terms: D000179:Acrylates / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D000977:Antiparasitic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D055772:Green Chemistry Technology / Q000191:economics / Q000379:methods*; D006801:Humans; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D007891:Leishmania / Q000187:drug effects*; D007896:Leishmaniasis / Q000188:drug therapy; D010879:Piperazines / Q000737:chemistry
chemical_list: D000179:Acrylates; D000447:Aldehydes; D000977:Antiparasitic Agents; D006841:Hydrocarbons, Aromatic; D010879:Piperazines; C035956:methyl acrylate; C007306:triethylenediamine