Efficient synthesis of 16 aromatic Morita-Baylis-Hillman adducts: Biological evaluation on Leishmania amazonensis and Leishmania chagasi.
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.
Junior
Cláudio G L
CG
Departamento de Química, Universidade Federal da Paraíba, João Pessoa, PB, Brazil.
de Assis
Priscila A C
PA
Silva
Fábio P L
FP
Sousa
Suervy C O
SC
de Andrade
Natália G
NG
Barbosa
Ticiano P
TP
Nerís
Patrícia L N
PL
Segundo
Luiz V G
LV
Anjos
Italo C
IC
Carvalho
Gabriel A U
GA
Rocha
Gerd B
GB
Oliveira
Márcia R
MR
Vasconcellos
Mário L A A
ML
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
D000179:Acrylates; D000447:Aldehydes; D000977:Antiparasitic Agents; D006841:Hydrocarbons, Aromatic; D010879:Piperazines; C035956:methyl acrylate; C007306:triethylenediamine