Synthesis and Anticancer Activities of Novel Guanylhydrazone and Aminoguanidine Tetrahydropyran Derivatives
Fábio Pedrosa Lins Silva,
Bruna Braga Dantas,
Gláucia Veríssimo Faheina Martins,
Demétrius Antônio Machado de Araújo,
Mário Luiz Araújo de Almeida Vasconcellos
Affiliations
Fábio Pedrosa Lins Silva
Departamento de Química, Campus I, Laboratório de Síntese Orgânica Medicinal da Paraíba (LASOM-PB), Universidade Federal da Paraíba, João Pessoa, CEP:58051-900, Paraíba, Brazil
Bruna Braga Dantas
Departamento de Biotecnologia, Campus I, Laboratório de Biotecnologia Celular e Molecular, Universidade Federal da Paraíba, João Pessoa, CEP:58051-900, Paraíba, Brazil
Gláucia Veríssimo Faheina Martins
Departamento de Biotecnologia, Campus I, Laboratório de Biotecnologia Celular e Molecular, Universidade Federal da Paraíba, João Pessoa, CEP:58051-900, Paraíba, Brazil
Demétrius Antônio Machado de Araújo
Departamento de Biotecnologia, Campus I, Laboratório de Biotecnologia Celular e Molecular, Universidade Federal da Paraíba, João Pessoa, CEP:58051-900, Paraíba, Brazil
Mário Luiz Araújo de Almeida Vasconcellos
Departamento de Química, Campus I, Laboratório de Síntese Orgânica Medicinal da Paraíba (LASOM-PB), Universidade Federal da Paraíba, João Pessoa, CEP:58051-900, Paraíba, Brazil
In this paper we present the convenient syntheses of six new guanylhydrazone and aminoguanidine tetrahydropyran derivatives 2–7. The guanylhydrazone 2, 3 and 4 were prepared in 100% yield, starting from corresponding aromatic ketones 8a–c and aminoguanidine hydrochloride accessed by microwave irradiation. The aminoguanidine 5, 6 and 7 were prepared by reduction of guanylhydrazone 2–4 with sodium cyanoborohydride (94% yield of 5, and 100% yield of 6 and 7). The aromatic ketones 8a–c were prepared from the Barbier reaction followed by the Prins cyclization reaction (two steps, 63%–65% and 95%–98%). Cytotoxicity studies have demonstrated the effects of compounds 2–7 in various cancer and normal cell lines. That way, we showed that these compounds decreased cell viabilities in a micromolar range, and from all the compounds tested we can state that, at least, compound 3 can be considered a promising molecule for target-directed drug design.
