Abstract
The equimolar reaction between 4-(di-methyl-amino)-benzaldehyde and 2-acetyl-thio-phene in basic ethano-lic solution yields the title compound, C15H15NOS, whose mol-ecular structure matches the asymmetric unit. The mol-ecule is not planar, the dihedral angle between the aromatic and the thio-phene rings being 11.4 (2)°. In the crystal, mol-ecules are linked by C-H⋯O and weak C-H⋯S inter-actions along [100], forming R22 (8) rings, and by weak C-H⋯O inter-actions along [010], forming chains with a C(6) graph-set motif. In addition, mol-ecules are connected into centrosymmetric dimers by weak C-H⋯π inter-actions, as indicated by the Hirshfeld surface analysis. The most important contributions for the crystal structure are the H⋯H (46.50%) and H⋯C (23.40%) inter-actions. The crystal packing resembles a herringbone arrangement when viewed along [100]. A mol-ecular docking calculation of the title compound with the neuraminidase enzyme was carried out. The enzyme shows (ASN263)N-H⋯O, (PRO245)C-H⋯Cg(thio-phene ring) and (AGR287)C-H⋯N inter-molecular inter-actions with the title compound. The crystal structure was refined as a two-component twin with a fractional contribution to the minor domain of 0.0181 (8).
Highlights
Gabriela Porto de Oliveira,a Leandro Bresolin,a* Darlene Correia Flores,a Renan Lira de Fariasb and Adriano Bof de Oliveirac
Molecules are linked by C— HÁ Á ÁO and weak C—HÁ Á ÁS interactions along [100], forming R22(8) rings, and by weak C—HÁ Á ÁO interactions along [010], forming chains with a C(6) graph-set motif
Molecules are connected into centrosymmetric dimers by weak C—HÁ Á Á interactions, as indicated by the Hirshfeld surface analysis
Summary
Chalcone derivatives are compounds with an aromatic conjugated enone as the main fragment and are synthesized by hydroxide-catalysed aldol condensation between an aromatic aldehyde and a ketone. Several 4-dialkylaminochalcones have shown antiproliferative activity on cancer cell lines and one method to monitor the chalcone–protein interaction, e.g. tubulin proteins, is the chalcone’s fluorescence (Zhou et al, 2016). Another example of the pharmacological background for the title compound and its derivatives is the anti-influenza viral activity through the neuraminidase enzymatic inhibition in vitro (Kinger et al, 2012). The crystal structure determination of chalcone-based molecules is an intensive research area, in particular for its contributions in medicinal chemistry. Symmetry codes: (i) x þ 1; y; z; (ii) Àx À 12; y À 12; Àz þ 32; (iii) Àx; Ày; Àz þ 1
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