Structural features of Novel 2,6-diarylpiperidin-4-ones derived from the methyl ether of raspberry ketone: Investigation through spectral, single crystal and DFT studies

Shanthi, D.; Rajeswari, K.; Kumar, C. Udhaya; Vidhyasagar, T.; Pillai, M. Velayutham

doi:10.1016/j.molstruc.2019.126907

Cited by 2 publications

(2 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is that 2.00 ppm and 2.22 ppm protons are connected to the same carbon and this may be characteristic of H-7A and H-7B protons. [42] Likewise, a multiplet observed in up field region with one proton integral value at 2.73 ppm exhibits a strong cross peak with 3.78 ppm and doublet observed 3.78 ppm gives cross peak with a multiplet signal at 2.73 ppm. Two cross peaks concluded that two signals (2.73 ppm and 3.78 ppm) are neighbouring protons with each other and this may be characteristic with H-3 and H-2 protons.…”

Section: D Nmr Spectral Analysis Of 4 Amentioning

confidence: 96%

Synthesis, Spectroscopic, Computational, Biological and Molecular docking studies on 3‐allyl 2,6‐diaryl piperidin‐4‐ones

Manjula

Venkateswaramoorthi²,

Dharmaraja³

et al. 2022

ChemistrySelect

View full text Add to dashboard Cite

A series of 3‐allyl‐2,6‐diarylpiperidin‐4‐one derivatives were designed and synthesized as antimicrobial agents with good yields. The target compounds were characterized by Mass, NMR, FT‐IR and FT‐Raman spectral techniques. The optimization had been performed on the title compound using the B3LYP method with 6‐311++G(d,p) basis set. The optimized bond parameter of the title molecule was calculated by DFT method. To study the intramolecular charge transfer within the molecule, the Lewis (bonding) and Non‐Lewis (anti‐bonding) structural calculation was performed. The Non‐linear optical behaviour of the title compound was measured using first order hyperpolarizability calculation. Mulliken atomic charges and thermodynamic properties were also calculated and analyzed. In vitro antibacterial and antifungal screening for all the synthesized 3‐allyl 2,6‐diaryl piperidin‐4‐ones was evaluated for two Gram‐positive bacteria (Staphylococcus aurous, Enterococcus faecalis), three Gram‐negative bacteria Pseudomonas aeruginosa, Escherichia coliand K. pneumonia) and five fungi (Candida albicans, Aspergillus niger, Aspergillus flavus, Rhizopus sp and Mucor sp). All the compounds showed good antibacterial and antifungal activities. Molecular docking study is to demonstrate that piperidine derivatives bind to Ribonucleotide reductases (RNRs) enzymes and to evaluate whether these molecules can be used as potential drugs.

show abstract

Section: D Nmr Spectral Analysis Of 4 Amentioning

confidence: 96%

Synthesis, Spectroscopic, Computational, Biological and Molecular docking studies on 3‐allyl 2,6‐diaryl piperidin‐4‐ones

Manjula

Venkateswaramoorthi²,

Dharmaraja³

et al. 2022

ChemistrySelect

View full text Add to dashboard Cite

show abstract

“…A successful piperidine ring cyclization was achieved by a Mannich condensation reaction from raspberry ketone methyl ether, as demonstrated by Shanthi et al 128 Thus, piperidinone with cyclic β-aminoketone moieties 83 was synthesized by the multicomponent Mannich reaction of methyl ether of raspberry ketone with aryl aldehydes, and ammonium acetate under reflux and catalyst-free conditions (Scheme 29). The stereochemistry of the constructed piperidinones was verified by the perceived coupling constants, in which the chair configuration with the substituents preferred the equatorial orientation, as estimated by 2D-NMR.…”

Section: Synthetic Approachesmentioning

confidence: 99%