5554-55-2Relevant academic research and scientific papers
Synthesis and characterization of piperidin-4-one derivatives using green solvent
Hemalatha,Ilangeswaran
, p. 981 - 984 (2020/03/24)
A deep eutectic solvent of glucose-urea was found to be an inexpensive and effective reaction medium in the synthesis of piperidin-4-one derivatives. In this work, 3-methyl-2,6-diphenyl piperidin-4-one (4a), 3,5-dimethyl-2,6-diphenylpiperidin-4-one (4b), 2,6-diphenylpiperidin-4-one (4c), piperidin-4-one (4d), 3,5-dimethylpiperidin-4-one (4e), 3-methyl-2,6-di(2-hydroxyphenyl)piperidin-4-one (4f), 3,5-dimethyl 2,6-di(2-hydroxyphenyl)piperidin-4one (4g) were synthesized using a deep eutectic solvent (DES) of glucose and urea with the percentage composition of 60:40. The yields of these products were 82, 78, 75, 68, 72, 70 and 70 %, respectively. The products obtained were characterized by FT-IR and 1H NMR spectroscopic techniques. A synthesis of piperidin-4-one derivatives by using this green solvent was considered to be new environmentally safe synthetic method.
Microwave assisted deprotection of heterocyclic semicarbazones by quinolinium flurochromate
Vimala,Santhi,Anusha
, p. 2296 - 2298 (2017/10/05)
The regeneration of semicarbazone from 2,6-diphenyl piperidine-4-one semicarbazone (PPS) and its alkyl substituted derivatives (3, 3 and 5th position) by quinolinium flurochromate (QFC) under microwave irradiation in the presence of montmorillonite K10 clay leads to the formation of ketone in a good yield.
Regeneration of carbonyl compounds by deoximation of piperidine-4-one oximes with quinolinium flurochromate in presence of montmorillonite K10 clay
Vimala,Lingeswari
, p. 2485 - 2487 (2017/10/31)
The regeneration of oximes from 2,6-diphenyl piperidine-4-one oximes (PPO) and its alkyl substituted derivatives (3-alkyl PPO and 3,5- dimethyl PPO) by quinolinium flurochromate under microwave irradiation in the presence of montmorillonite K10 clay leads to the formation of ketone in a good yield.
New piperidine-hydrazone derivatives: Synthesis, biological evaluations and molecular docking studies as AChE and BChE inhibitors
Karaman, Nurcan,S?cak, Yusuf,Ta?k?n-Tok, Tu?ba,?ztürk, Mehmet,Karakü?ük-?yido?an, Ay?egül,Dikmen, Miris,Ko?yi?it-Kaymak??o?lu, Bedia,Oru?-Emre, Emine El?in
, p. 270 - 283 (2016/09/09)
Hydrazones and the piperidine ring containing compounds were considered as beneficial substrates in drug design. Therefore, this study was aimed at the synthesis of new benzoyl hydrazones derived from ethyl 4-oxopiperidine-1-carboxylate and 2,6-diphenylpiperidin-4-one. The synthesized compounds (1?19) were screened for their antioxidant, anticholinesterase and anticancer activities. The antioxidant capacity of the compounds was evaluated by using four complementary tests. The results showed that compound 7 and 17 have the higher lipid peroxidation inhibitory activity than the other compounds. In DPPH˙ scavenging assay, compounds 5, 6, 10, 14, 17 demonstrated better activity than that of standard BHT, while in ABTS+˙ scavenging assay compound 6 and 17 exhibited better activity among the other compounds. The CUPRAC assay disclosed that compound 2 displayed better activity than α-tocopherol. The anticholinesterase activity was performed against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. Compound 11 (IC50: 35.30?±?1.11?μM) inhibited BChE better than galantamine (IC50: 46.03?±?0.14?μM). We conclude that the compound 11 can be considered as a candidate for BChE inhibitor. Moreover docking method was applied to elucidate the AChE and BChE inhibitory mechanism of the compound 11. Molecular docking analysis revealed that compound 11 bound to BChE enzyme more efficiently when compared to the AChE due to its orientations and different types of interactions. In addition, the non-cytotoxic properties of the compounds brought them into prominence, although they did not show significant anticancer properties.
Microwave-assisted synthesis of new sulfonyl hydrazones, screening of biological activities and investigation of structure–activity relationship
Karaman, Nurcan,Oru?-Emre, Emine El?in,S?cak, Yusuf,?at?kka?, Berna,Karakü?ük-?yido?an, Ay?egül,?ztürk, Mehmet
, p. 1590 - 1607 (2016/07/30)
Abstract: Sulfonyl hydrazone scaffold and the piperidine rings have important role in medicinal chemistry. This study shows the synthesis of two novel series of sulfonyl hydrazone having piperidine derivatives by condensing benzene sulfonyl hydrazides with ethyl 4-oxopiperidine-1-carboxylate and 2,6-diphenylpiperidin-4-one. Physical and chemical properties of compounds have been characterized and reported by utilizing their melting point, elemental analysis, IR, 1H-NMR, 13C NMR, 2D NMR and mass spectra results. Synthesized compounds were evaluated for antioxidant capacity and anticholinesterase activity. The antioxidant capacity of the compounds were screened through four complementary test, i.e., β-carotene–linoleic acid for lipid peroxidation, DPPH free radical (DPPH·), ABTS cation radical (ABTS+·) and CUPRAC assays. Assay results showed that N′-(2,6-diphenylpiperidin-4-ylidene)-4-bromobenzenesulfonohydrazide (11) has the highest lipid peroxidation inhibitory activity. Within the assay series, N′-(2,6-diphenylpiperidin-4-ylidene)-4-bromobenzenesulfonohydrazide (11) exhibited better activity than standard BHT in DPPH· scavenging, while N′-(2,6-diphenylpiperidin-4-ylidene)benzenesulfonohydrazide (10) showed the best ABTS+· scavenging assay. The CUPRAC assay revealed that ethyl 4-(2-(4-methoxyphenylsulfonyl)hydrazono)piperidine-1-carboxylate (5) indicated the best activity with A0.50 value among the tested compounds than the antioxidant standard α-tocopherol. According to AChE assay, N′-(2,6-diphenylpiperidin-4-ylidene)-4-chlorobenzenesulfonohydrazide (12) had the best activity, while in BChE assay the highest activity was found for compound N′-(2,6-diphenylpiperidin-4-ylidene)-4-methylbenzenesulfonohydrazide (16). Electronic and structural characteristics and density functional studies of the all newly synthesized compounds have been reported for better understanding in molecular-level. NMR, molecular electrostatic potential (MEP), ΔEHOMO–LUMO band gap and the dipole moments of the molecules have been also analyzed and reported. Graphical Abstract: [Figure not available: see fulltext.]
Synthesis, spectral studies and in vitro antibacterial evaluation of triaza and dioxa aza spiro derivatives
Natarajan, Manivannan,Balachandravinayagam, Elanchezhian,Selvaraju, Meenakshi,Ganesan, Selvanathan
, p. 277 - 281 (2013/02/22)
Six compounds 7,9-diphenyl-1,4-dioxa-8-azaspiro[4.5]decane 1-6 have been synthesized by Mannich reaction and cyclo condensation. The structures and stereochemistry established by IR, NMR studies. The purities were checked by elemental analysis. The synthesized compounds 1-6 adopt chair conformation with equatorial orientation of the aryl groups. All the compounds were screened for their antibacterial activity against Proteus mirabilis, Klebsiella oxytoca, Staphylococcus aureus and Salmonella paratyphi. The compound 5 exhibited excellent in vitro antibacterial activity in all species.
Synthesis, NMR spectral studies and antimicrobial evaluation of some 2-(benzothiazol-2-yl)-1-(alkyl-2r,6c-diarylpiperidin-4-ylidine)hydrazine derivatives
Xavier, J. John Francis,Venkateswaramoorthi,Kamaraj,Krishnasamy
, p. 5105 - 5111 (2013/12/04)
Substituted 2-(benzothiazol-2-yl)-1-(alkyl-2,6-diarylpiperidin-4-ylidine) hydrazines 10-17 were synthesized by the condensation of different 2r,6c-diarylpiperidin-4-ones 1-8 with 2-hydrazinobenzothiazole 9. All the synthesized compounds were investigated in solution and in the solid state by IR, 1H, 13C and 2D NMR spectral techniques. The structure-activity relationships were studied by the screening of the antimicrobial activity over a representative panel of bacterial and fungal strains using two-fold serial dilution method.
Synthesis and stereodynamics of N-Formyl-1,2,3-selenadiazolopyridines
Ingarsal,Amutha,Gopalakrishnan,Nagarajan
body text, p. 515 - 522 (2012/03/26)
The 4,6-diaryl-6,7-dihydro-[1,2,3]selenadiazolo[5,4-c]pyridine-5(4H)- carbalde hydes were synthesized from 2,6-diarylpiperidin-4-ones and characterized using infrared, 1H, 13C Nuclear Magnetic Resonance (NMR), and mass spectroscopic techniques. On the NMR time scale, the compounds exist in syn and anti isomeric forms. Separate signals were obtained for isomers in the NMR spectra. The compounds stereodynamic nature was studied based on the intensity and position of NMR signals. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
Design, synthesis, spectral and biological evaluation of novel 1-allyl substituted 2,6-diphenylpiperidin-4-ones and its derivatives of oximes/oxime ethers
Narayanan, Kuppusamy,Shanmugam, Mani,Jothivel, Sarangan,Kabilan, Senthamaraikannan
, p. 6602 - 6607,6 (2012/12/12)
A series of 1-allyl-2,6-diphenylpiperidin-4-one oximes 17-24 and 1-allyl-2,6-diphenylpiperidin-4-one O-benzyloximes 25-32 were synthesized from respective 1-allyl-2,6-diphenylpiperidin-4-ones 9-16. The structure and the conformations have been investigated for all the synthesized compounds 9-32 by analytical and spectral techniques (IR, Mass, 1H, 13C, 2D NMR and X-ray Diffraction). Based on the proton NMR analysis, all the synthesized compounds 9-32, exposed chair conformation except compounds 22 and 30 (twist boat conformation). For all the synthesized compounds 9-32 antimicrobial activity has been carried out against a panel of selected bacterial and fungal strains using Streptomycin and Amphotericin B as standards. Antibacterial and antifungal activity of compounds 19, 21, 23 (allyl oximes) 25-29, 31, 32 (allyl oxime ethers) and 11, 13 (ketones) exerted moderate to excellent activity against Staphylococcus aureus, Bacillus subtilis, Salmonella typhi bacterial strains and Penicillium chrysogenum, Aspergillus niger, Fusarium oxysporum fungal strains. The MIC results of all the synthesized compounds revealed that most of the oxime ether compounds exhibit excellent activity against selected bacterial and fungal strains.
1H and 13C NMR spectral study of some 3,5-bis[(E)-thienylmethylene]piperidin-4-ones
Rajeswari,Pandiarajan
scheme or table, p. 1110 - 1118 (2011/04/16)
1H and 13C NMR spectra have been recorded for 3,5-bis[(E)-thienylmethylene]piperidin-4-one (1a), 3′,3″-dimethyl-3, 5-bis[(E)-thienylmethylene]piperidin-4-one (1b), 5′,5″-dibromo-3,5- bis[(E)-thienylmethylene]piperidin-4-one (1c), the
