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Molecules 2016, 21(6), 671; doi:10.3390/molecules21060671

Synthesis and Anticancer Activities of Novel Guanylhydrazone and Aminoguanidine Tetrahydropyran Derivatives

1
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
2
Departamento de Biotecnologia, Campus I, Laboratório de Biotecnologia Celular e Molecular, Universidade Federal da Paraíba, João Pessoa, CEP:58051-900, Paraíba, Brazil
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 28 March 2016 / Revised: 5 May 2016 / Accepted: 11 May 2016 / Published: 21 June 2016
(This article belongs to the Section Bioorganic Chemistry)
View Full-Text   |   Download PDF [648 KB, uploaded 21 June 2016]   |  

Abstract

In this paper we present the convenient syntheses of six new guanylhydrazone and aminoguanidine tetrahydropyran derivatives 27. The guanylhydrazone 2, 3 and 4 were prepared in 100% yield, starting from corresponding aromatic ketones 8ac and aminoguanidine hydrochloride accessed by microwave irradiation. The aminoguanidine 5, 6 and 7 were prepared by reduction of guanylhydrazone 24 with sodium cyanoborohydride (94% yield of 5, and 100% yield of 6 and 7). The aromatic ketones 8ac 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 27 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. View Full-Text
Keywords: Prins cyclization reaction; tetraydropyran derivatives; anticancer; guanylhydrazone; aminoguanidine Prins cyclization reaction; tetraydropyran derivatives; anticancer; guanylhydrazone; aminoguanidine
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MDPI and ACS Style

Silva, F.P.L.; Dantas, B.B.; Faheina Martins, G.V.; de Araújo, D.A.M.; Vasconcellos, M.L.A.A. Synthesis and Anticancer Activities of Novel Guanylhydrazone and Aminoguanidine Tetrahydropyran Derivatives. Molecules 2016, 21, 671.

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