Conformational variability in sulfonamide chalcone hybrids: crystal structure and cytotoxicity
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Data
2016
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Resumo
Four sulfonamide-chalcone derivatives were prepared and their crystal structure were
elucidated by single-crystal X-ray diffraction technique. They were synthesized by Claisen-Schmidt
condensation reaction between N-(4-acetylphenyl)benzenesulfonamide or N-(4-acetylphenyl)-
2,5-dichlorobenzenesulfonamide with benzaldehyde or p-nitrobenzaldehyde. Values of Z’ > 1
are found in three compounds as a consequence of conformerism. The chalcone molecular
backbones are featured by different levels of planarity in their conformers. Another conformational
variability is in its benzenesulfonamide moiety. In the compound came from N-(4-acetylphenyl)
benzenesulfonamide and benzaldehyde, there is a rotation of ca. 180° on the bond axis bridging
the sulfonamide and chalcone motifs of one conformer if the two others are taken as references.
The cytotoxic activity of all compounds synthesized here and of two other related sulfonamide
chalcones was also assessed against three cancer cell lines (SF-295, HCT-8 and MDA-MB-435). The
para-nitro compounds were the most active ones among all those tested, regardless of substitution
pattern in benzenesulfonamide core.
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Structural analyses, Structure determination, Structure-activity relationship, Biological and pharmacological activities, Bioactive compounds, Molecular structure
Citação
CASTRO, Mirian R. C. et al. Conformational variability in sulfonamide chalcone hybrids: crystal structure and cytotoxicity. Journal of the Brazilian Chemical Society, Campinas, v. 27, n. 5, p. 884-898, 2016.