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Synthesis and activity of novel homodimers of Morita–Baylis–Hillman adducts against Leishmania donovani: A twin drug approach

2016; Elsevier BV; Volume: 26; Issue: 18 Linguagem: Inglês

10.1016/j.bmcl.2016.07.022

1464-3405

Wagner A.V. da Silva, Daniele C. Rodrigues, Ramon G. de Oliveira, Rhuan Karlos Santos Mendes, Tayná Rodrigues Olegário, Juliana C. Rocha, Tatjana Souza Lima Keesen, Cláudio Gabriel Lima-Júnior, Mário L. A. A. Vasconcellos,

Phytochemistry and biological activities of Ficus species

It is reported here the synthesis of novel Homodimers 12-19 of Morita-Baylis-Hillman adducts (MBHA) from one-pot Morita-Baylis-Hillman Reaction (MBHR) between aromatic aldehydes as eletrophiles and ethylene glycol diacrylate as Michael acceptor (35-94% yields) using cheap and green conditions. The bioactivities were evaluated against promastigote form of Leishmania donovani. All homodimers showed to be more potent than corresponding monomers. It is worth highlighting that the halogenated homodimers 17 and 18 (0.50μM) is almost 400 times more active than the corresponding monomer 10 and 1.24 times more potent than the second-line drug amphotericin B (0.62μM). Moreover, the selectivity index to 18 is very high (SIrb>400) far better than amphotericin B (SIrb=18.73). This is the first report of twin drugs strategy applied on Morita-Baylis-Hillman adducts.