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Preliminary antifungal and cytotoxic evaluation of synthetic cycloalkyl[b]thiophene derivatives with PLS-DA analysis

2012; De Gruyter Open; Volume: 62; Issue: 2 Linguagem: Inglês

10.2478/v10007-012-0017-y

1846-9558

Beatriz J. Souza, Tiago De Oliveira, Thiago Mendonça de Aquino, Maria C. Pedroso de Lima, Ivan da Rocha Pitta, Suely Lins Galdino, Edeltrudes de Oliveira Lima, Teresinha Gonçalves-Silva, Gardênia Carmen Gadelha Militão, Luciana Scotti, Marcus Tullius Scotti, Francisco Jaime Bezerra Mendonça,

Synthesis of Organic Compounds

Preliminary antifungal and cytotoxic evaluation of synthetic cycloalkyl[ b ]thiophene derivatives with PLS-DA analysis A series of 2-[(arylidene)amino]-cycloalkyl[ b ]thiophene-3-carbonitriles ( 2a-x ) was synthesized by incorporation of substituted aromatic aldehydes in Gewald adducts ( 1a-c ). The title compounds were screened for their antifungal activity against Candida krusei and Criptococcus neoformans and for their antiproliferative activity against a panel of 3 human cancer cell lines (HT29, NCI H-292 and HEP). For antiproliferative activity, the partial least squares (PLS) methodology was applied. Some of the prepared compounds exhibited promising antifungal and proliferative properties. The most active compounds for antifungal activity were cyclohexyl[ b ]thiophene derivatives, and for antiproliferative activity cycloheptyl[ b ]thiophene derivatives, especially 2-[(1 H -indol-2-yl-methylidene)amino]- 5,6,7,8-tetrahydro-4 H -cyclohepta[ b ]thiophene-3-carbonitrile ( 2r ), which inhibited more than 97 % growth of the three cell lines. The PLS discriminant analysis (PLS-DA) applied generated good exploratory and predictive results and showed that the descriptors having shape characteristics were strongly correlated with the biological data.