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Molecules 2017, 22(2), 207;

Synthesis of 16 New Hybrids from Tetrahydropyrans Derivatives and Morita˗Baylis˗Hillman Adducts: In Vitro Screening against Leishmania donovani

Laboratório de Síntese Orgânica Medicinal da Paraíba (LASOM‐PB), Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, PB 58059‐900, Brazil
Departamento de Biotecnologia, Universidade Federal da Paraíba, Campus I, João Pessoa, PB 58059‐900, Brazil
Unidade Acadêmica de Saúde, Centro de Educação e Saúde, Universidade Federal de Campina Grande, Campus Cuité, Cuité, PB 58175‐000, Brazil
Instituto Federal de Educação, Ciência e Tecnologia da Bahia, Campus Catu, Barão de Camaçari, Catu, BA 48110‐000, Brazil
Programa de Pós‐Graduação em Ciências Fisiológicas and Laboratório de Farmacologia, Departamento Ciências Fisiológicas, Instituto de Ciências e Saúde, Universidade Federal Rural do Rio de Janeiro Seropédica, RJ 23890‐000, Brazil
Authors to whom correspondence should be addressed.
Received: 19 December 2016 / Accepted: 25 January 2017 / Published: 30 January 2017
(This article belongs to the Special Issue Emerging Drug Discovery Approaches against Infectious Diseases)
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Leishmaniases are a group of neglected tropical diseases (NTDs) caused by protozoan parasites from >20 Leishmania species. Visceral leishmaniasis (VL), also known as kala‐aza, is the most severe form of leishmaniasis, usually fatal in the absence of treatment in 95% of cases. The Morita‐Baylis‐Hillman adducts (MBHAs) are being explored as drug candidates against several diseases, one of them being leishmaniasis. We present here the design, synthesis and in vitro screening against Leishmania donovani of sixteen new molecular hybrids from analgesic/antiinflammatory tetrahydropyrans derivatives and Morita˗Baylis˗Hillman adducts. First, acrylates were synthesized from analgesic/anti‐inflammatory tetrahydropyrans using acrylic acid under TsOH as a catalyst (70–75% yields). After the 16 new MBHAs were prepared in moderate to good yields (60–95%) promoted by microwave irradiation or low temperature (0 °C) in protic and aprotic medium. The hybrids were evaluated in vitro on the promastigote stage of Leishmania donovani by determining their inhibitory concentrations 50% (IC50), 50% hemolysis concentration (HC50), selectivity index (HC50/IC50,), and comparing to Amphotericin B, chosen as the anti‐leishmanial reference drug. The hybrid which presents the bromine atom in its chemical structure presents high leishmanicide activity and the high selectivity index in red blood cells (SIrb > 180.19), compared with the highly‐toxic reference drug (SIrb = 33.05), indicating that the bromine hybrid is a promising compound for further biological studies. View Full-Text
Keywords: Antileishmanial Morita‐Baylis‐Hillman adducts; opioids tetrahydropyrans derivatives;  molecular hybridization; Leishmania donovani. Antileishmanial Morita‐Baylis‐Hillman adducts; opioids tetrahydropyrans derivatives;  molecular hybridization; Leishmania donovani.

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Sousa, S.C.O.; Rocha, J.C.; Keesen, T.S.L.; Silva, E.P.; de Assis, P.A.C.; de Oliveira, J.P.G.; Capim, S.L.; Xavier, F.J.S.; Marinho, B.G.; Silva, F.P.L.; Lima‐Junior, C.G.; Vasconcellos, M.L.A.A. Synthesis of 16 New Hybrids from Tetrahydropyrans Derivatives and Morita˗Baylis˗Hillman Adducts: In Vitro Screening against Leishmania donovani. Molecules 2017, 22, 207.

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