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  • Efficient synthesis of 16 aromatic Morita-Baylis-Hillman adducts: Biological evaluation on Leishmania amazonensis and Leishmania chagasi.

Efficient synthesis of 16 aromatic Morita-Baylis-Hillman adducts: Biological evaluation on Leishmania amazonensis and Leishmania chagasi.

Bioorganic chemistry (2010-09-22)
Cláudio G L Junior, Priscila A C de Assis, Fábio P L Silva, Suervy C O Sousa, Natália G de Andrade, Ticiano P Barbosa, Patrícia L N Nerís, Luiz V G Segundo, Italo C Anjos, Gabriel A U Carvalho, Gerd B Rocha, Márcia R Oliveira, Mário L A A Vasconcellos
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Methyl acrylate, 99%, contains ≤100 ppm monomethyl ether hydroquinone as inhibitor
Supelco
Methyl acrylate, analytical standard