1470003-84-9Relevant academic research and scientific papers
Synthesis and anticancer activities of novel guanylhydrazone and aminoguanidine tetrahydropyran derivatives
Silva, Fábio Pedrosa Lins,Dantas, Bruna Braga,Martins, Gláucia Veríssimo Faheina,De Araújo, Demétrius Ant?nio Machado,Vasconcellos, Mário Luiz Araújo De Almeida
, (2016/07/06)
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 aminoguanidi
Microwave-assisted stereospecific synthesis of novel tetrahydropyran adenine isonucleosides and crystal structures determination
Silva, Fábio P.L.,Cirqueira, Marilia L.,Martins, Felipe T.,Vasconcellos, Mário L.A.A.
, p. 189 - 196 (2013/10/08)
We describe in this article stereospecific syntheses for new isonucleosides analogs of adenine 5-7 from tosyl derivatives 2-4 accessing by microwave irradiations (50-80%). The adenine reacts entirely at the N(9) position. Compounds 2-4 were prepared in two steps from the corresponding alcohols 1, 8 and 9 (81-92%). These tetrahydropyrans alcohols 1, 8 and 9 are achiral (Meso compounds) and were prepared in two steps with complete control of 2,4,6-cis relative configuration by Prins cyclization reaction (60-63%) preceded by the Barbier reaction between allyl bromide with benzaldehyde, 4-fluorobenzaldehyde and 2-naphthaldehyde respectively under Lewis acid conditions (96-98%). The configurations and preferential conformations of 5-7 were determined by crystal structure of 6. These novel isonucleosides 5-7 present in silico potentiality to act as GPCR ligand, kinase inhibitor and enzyme inhibitor, evaluated by Molinspiration program, consistent with the expected antiviral and anticancer bioactivities.
