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Synthesis and Antileishmanial Activity of Natural Dehydrodieugenol and Its Mono‐ and Dimethyl Ethers
Author(s) -
Rodrigues Luis Cezar,
BarbosaFilho José Maria,
Oliveira Marcia Rosa,
Nascimento Néris Patrícia Lima,
Borges Flávio Valadares Pereira,
Mioso Roberto
Publication year - 2016
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201500280
Subject(s) - chemistry , potassium ferricyanide , eugenol , dimethyl ether , ether , potassium , organic chemistry , stereochemistry , medicinal chemistry , methanol
The study of chemistry of naturally occurring compounds and the synthesis of their derivatives is fundamentally important for the development of new drugs. In this work, dehydrodieugenol ( DHDE ) was obtained through oxidative coupling of eugenol, promoted by an aqueous mixture of potassium ferricyanide (K 3 [Fe( CN ) 6 ]) and NH 3 · H 2 O. The partial methoxylation of DHDE with MeI and K 2 CO 3 mainly resulted in the molecular‐shaped monomethyl ether ( DHDE ‐1MeO) and its dimethyl ether derivative ( DHDE ‐2MeO). The products from the reactions were characterized by 1 H‐ and 13 C‐ NMR spectroscopy. Additionally, these studies have reported the antileishmanial activity of DHDE against Leishmania amazonensis ( IC 50 value of 42.20 μg ml −1 ) and shown that partial methoxylation of DHDE results in a significant increase in its antiparasitic activity ( IC 50 value of 13.68 μg ml −1 ). Based on in vitro bioassays, DHDE ‐1MeO has shown the highest leishmanicidal activity in promastigota form. Production by direct one‐step synthesis of this monomethoxylated compound can be considered to be a cost‐effective and environmentally friendly method with a short reaction time.