新型胍基腙和氨基胍四氢吡喃衍生物的合成及其抗癌活性
Synthesis and Anticancer Activities of Novel Guanylhydrazone and Aminoguanidine Tetrahydropyran Derivatives.
作者信息
Silva Fábio Pedrosa Lins, Dantas Bruna Braga, Faheina Martins Gláucia Veríssimo, de Araújo Demétrius Antônio Machado, Vasconcellos Mário Luiz Araújo de Almeida
机构信息
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.
Departamento de Biotecnologia, Campus I, Laboratório de Biotecnologia Celular e Molecular, Universidade Federal da Paraíba, João Pessoa, CEP:58051-900, Paraíba, Brazil.
出版信息
Molecules. 2016 Jun 21;21(6):671. doi: 10.3390/molecules21060671.
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.
在本文中，我们展示了六种新型胍腙和氨基胍四氢吡喃衍生物2 - 7的简便合成方法。胍腙2、3和4以100%的产率制备，起始原料为相应的芳香酮8a - c和通过微波辐射获得的盐酸氨基胍。氨基胍5、6和7通过用氰基硼氢化钠还原胍腙2 - 4制备（5的产率为94%，6和7的产率为100%）。芳香酮8a - c通过巴比耶反应，然后进行普林斯环化反应制备（两步，产率分别为63% - 65%和95% - 98%）。细胞毒性研究表明了化合物2 - 7在各种癌细胞系和正常细胞系中的作用。通过这种方式，我们表明这些化合物在微摩尔范围内降低了细胞活力，并且从所有测试的化合物中我们可以得出，至少化合物3可以被认为是用于靶向药物设计的有前景的分子。
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