title: Synthesis and Anticancer Activities of Novel Guanylhydrazone and Aminoguanidine Tetrahydropyran Derivatives.
abstract: 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.
authors.affiliation: Departamento de Qu&#237;mica, Campus I, Laborat&#243;rio de S&#237;ntese Org&#226;nica Medicinal da Para&#237;ba (LASOM-PB), Universidade Federal da Para&#237;ba, Jo&#227;o Pessoa, CEP:58051-900, Para&#237;ba, Brazil. pedrosalinssilva@gmail.com.
authors.forename: Fábio Pedrosa Lins
authors.initials: FP
authors.lastname: Silva
authors.affiliation: Departamento de Biotecnologia, Campus I, Laborat&#243;rio de Biotecnologia Celular e Molecular, Universidade Federal da Para&#237;ba, Jo&#227;o Pessoa, CEP:58051-900, Para&#237;ba, Brazil. brunabdantas@gmail.com.
authors.forename: Bruna Braga
authors.initials: BB
authors.lastname: Dantas
authors.affiliation: Departamento de Biotecnologia, Campus I, Laborat&#243;rio de Biotecnologia Celular e Molecular, Universidade Federal da Para&#237;ba, Jo&#227;o Pessoa, CEP:58051-900, Para&#237;ba, Brazil. glauciafaheina@yahoo.com.br.
authors.forename: Gláucia Veríssimo
authors.initials: GV
authors.lastname: Faheina Martins
authors.affiliation: Departamento de Biotecnologia, Campus I, Laborat&#243;rio de Biotecnologia Celular e Molecular, Universidade Federal da Para&#237;ba, Jo&#227;o Pessoa, CEP:58051-900, Para&#237;ba, Brazil. demetrius@cbiotec.ufpb.br.
authors.forename: Demétrius Antônio Machado
authors.initials: DA
authors.lastname: de Araújo
authors.affiliation: Departamento de Qu&#237;mica, Campus I, Laborat&#243;rio de S&#237;ntese Org&#226;nica Medicinal da Para&#237;ba (LASOM-PB), Universidade Federal da Para&#237;ba, Jo&#227;o Pessoa, CEP:58051-900, Para&#237;ba, Brazil. mlaav@quimica.ufpb.br.
authors.forename: Mário Luiz Araújo de Almeida
authors.initials: ML
authors.lastname: Vasconcellos
mesh_terms: D001894:Borohydrides / Q000138:chemical synthesis / Q000737:chemistry; D045744:Cell Line, Tumor; D003500:Cyclization; D006146:Guanidines / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D006835:Hydrazones / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy*; D011714:Pyrans / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001894:Borohydrides; D006146:Guanidines; D006835:Hydrazones; D007659:Ketones; D011714:Pyrans; C009282:sodium cyanoborohydride; C004479:pimagedine
keywords: Prins cyclization reaction; aminoguanidine; anticancer; guanylhydrazone; tetraydropyran derivatives