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

We described “one-pot” Morita-Baylis-Hillman reactions to produced 16 aromatic compounds (81-100%), its bio-evaluations on L. Amazonensis and L. chagasi and a relationship between the chemical structure and biological activity (S.A.R.). Sixteen aromatic Morita–Baylis–Hillman adducts (MBHA) 1– 16 wer...

Full description

Saved in:

Bibliographic Details
Published in:	Bioorganic chemistry Vol. 38; no. 6; pp. 279 - 284
Main Authors:	Junior, Cláudio G.L., de Assis, Priscila A.C., Silva, Fábio P.L., Sousa, Suervy C.O., de Andrade, Natália G., Barbosa, Ticiano P., Nerís, Patrícia L.N., Segundo, Luiz V.G., Anjos, Ítalo C., Carvalho, Gabriel A.U., Rocha, Gerd B., Oliveira, Márcia R., Vasconcellos, Mário L.A.A.
Format:	Journal Article
Language:	English
Published:	United States Elsevier Inc 01-12-2010
Subjects:	Acrylates - chemistry Aldehydes - chemistry Antiparasitic Agents - chemical synthesis Antiparasitic Agents - chemistry Antiparasitic Agents - pharmacology Catalysis Drugs Green Chemistry Technology - economics Green Chemistry Technology - methods Humans Hydrocarbons, Aromatic - chemical synthesis Hydrocarbons, Aromatic - chemistry Hydrocarbons, Aromatic - pharmacology Leishmania Leishmania - drug effects Leishmania amazonensis Leishmania chagasi Leishmaniasis - drug therapy Morita–Baylis–Hillman adducts Piperazines - chemistry Structure–activity-relationship Temperature effect Drugs Temperature effect Structure–activity-relationship Morita–Baylis–Hillman adducts Leishmania
Online Access:	Get full text
Tags:	Add Tag No Tags, Be the first to tag this record!

Description
Summary:	We described “one-pot” Morita-Baylis-Hillman reactions to produced 16 aromatic compounds (81-100%), its bio-evaluations on L. Amazonensis and L. chagasi and a relationship between the chemical structure and biological activity (S.A.R.). 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 (IC 50 values of 6.88 μg mL −1 and 11.06 μg mL −1 respectively on L. amazonensis; 9.58 μg mL −1 and 14.34 μg mL −1 respectively on L. chagasi) indicates that these MBHA can be a novel and promising class of anti-parasitic compounds.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0045-2068 1090-2120
DOI:	10.1016/j.bioorg.2010.08.002