Original scientific paper

https://doi.org/10.2478/v10007-012-0017-y

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

BEATRIZ C. C. SOUZA ; Departamento de Antibióticos, Universidade Federal de Pernambuco, Recife-PE 50670-910,Brazil
TIAGO B. DE OLIVEIRA ; Departamento de Antibióticos, Universidade Federal de Pernambuco, Recife-PE 50670-910,Brazil
THIAGO M. AQUINO ; Departamento de Antibióticos, Universidade Federal de Pernambuco, Recife-PE 50670-910,Brazil
MARIA C. A. DE LIMA ; Departamento de Antibióticos, Universidade Federal de Pernambuco, Recife-PE 50670-910,Brazil
IVAN R. PITTA ; Departamento de Antibióticos, Universidade Federal de Pernambuco, Recife-PE 50670-910,Brazil
SUELY L. GALDINO ; Departamento de Antibióticos, Universidade Federal de Pernambuco, Recife-PE 50670-910,Brazil
EDELTRUDES O. LIMA ; Departamento de Ciências Farmacêuticas, Universidade Federal da Paraíba, João Pessoa-PB, 58051-970, Brazil
TERESINHA GONÇALVES-SILVA ; Departamento de Antibióticos, Universidade Federal de Pernambuco, Recife-PE 50670-910,Brazil
GARDÊNIA C. G. MILITÃO ; Departamento de Antibióticos, Universidade Federal de Pernambuco, Recife-PE 50670-910,Brazil
LUCIANA SCOTTI ; Departamento de Ciências Farmacêuticas, Universidade Federal da Paraíba, João Pessoa-PB, 58051-970, Brazil
MARCUS T. SCOTTI ; Departamento de Engenharia e Meio Ambiente, Universidade Federal da Paraíba, Campus IV; Rio Tinto-PB 58297-000, Brazil
FRANCISCO J. B. MENDONÇA Jr. orcid.org/0000-0003-3588-833X ; Departamento de Ciências Biológicas, Universidade Estadual da Paraíba, CCBSA, João Pessoa-PB 58070-450, Brazil

Abstract

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 Criptococcusneoformans and for their antiproliferative activity against a panel of 3 human cancer cell lines (HT29, NCI H-292 and HEP). Forantiproliferative 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 forantiproliferative activity cycloheptyl[b]thiophene derivatives, especially 2-[(1H-indol-2-yl-methylidene)amino]-5,6,7,8-tetrahydro-4H-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.

Keywords

cycloalkyl[b]thiophene derivatives; antifungal activity; antiproliferative activity; PLS-DA; Pentacle program

Hrčak ID:

80582

URI

https://hrcak.srce.hr/80582

Publication date:

30.6.2012.

Article data in other languages: croatian

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