Synthesis, characterization, stereochemistry, biological investigation and DNA binding studies on N-acyl-t-3-ethyl-r-2,c-6-bis(4-methoxyphenyl)piperidin-4-ones

作者：Mohanraj V.; Ponnuswamy S.^*; Mohanraj V.; Ponnuswamy S^*

来源：Journal of Molecular Structure, 2018, 1171: 420-428.

DOI：10.1016/j.molstruc.2018.05.102

• N-Acyl piperidin-4-ones
• Boat conformation
• Antibacterial
• Antifungal
• Antioxidant
• DNA binding

t-3-Ethyl-r-2,c-6-bis(4-methoxyphenyl)piperidin-4-one (1) and its N-phenylcarbamoyl, N-acetyl and N-chloroacetyl derivatives 2-4, respectively have been synthesized and characterized using IR, H-1, C-13, DEPT-135 & 2D NMR and mass spectral studies. The NMR spectral data indicate that the N-acyl-r-2,c-6-bis(4-methoxyphenyl)piperidin-4-ones 2-4 prefer to exist in a boat conformation B-1 with N-C=O rotational equilibrium. All the compounds show prominent antibacterial activity against the organism S. faecalis and the N-phenylcarbamoyl derivative 2 shows significant activity towards s. paratyphi. Further the compounds 3 & 4 are found to be inactive against all the fungal species studied and the compounds 1 & 2 show moderate activity against mucor species and A. lipoferum, respectively. The compounds 1-4 show moderate antioxidant activities (DPPH) with standard references viz., Rutin and BHT. Further, the DNA binding studies on these compounds 1-4 have been carried out using Calf Thymus DNA. The compounds 1, 3 & 4 possess good binding affinity with DNA. The binding constant for compounds 1, 3 & 4 varies in the range of 5.5-0.15 x 10(4) M-1.