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Journal articles on the topic 'Piperidone'

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Published: 5 June 2025

Last updated: 1 August 2025

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1

Romero-Ibañez, Julio, Marina A. Ortega-Rojas, Jonathan R. Valdéz-Camacho, Luis G. Hernández-Vázquez, Fernando Sartillo-Piscil, and Jaime Escalante. "Asymmetric Synthesis of trans-3-Alkoxyamino-4-Oxygenated-2-Piperidones Mediated by Transition-Metal-Free Dual C-H Oxidation and Its CAL-B-Assisted Enzymatic Resolution." Catalysts 13, no. 4 (2023): 703. http://dx.doi.org/10.3390/catal13040703.

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A general chemo-enzymatic approach to synthesize both enantioenriched trans-3-alkoxyamino-4-oxy-2-piperidones, which are important scaffold for various naturally occurring alkaloids, is reported. To this end, a selective transition-metal-free dual C−H oxidation of piperidines mediated by the TEMPO oxoammonium cation (TEMPO+) was used, followed by enzymatic resolution of the corresponding alkoxyamino-2-piperidones with Candida antarctica lipase (CAL-B), to yield the title compounds in high enantiomeric excess (ee). The absolute configuration of both enantioenriched compounds was determined usin

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2

Holzgrabe, Ulrike, Willy Friedrichsen, and Karl-F. Hesse. "Keto-Enol-Tautomerism and Configurational Isomerism of 2,6-Disubstituted 4-Piperidone-3,5-dicarboxylates." Zeitschrift für Naturforschung B 46, no. 9 (1991): 1237–50. http://dx.doi.org/10.1515/znb-1991-0918.

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The dialkyl 2,6-dialkylsubstituted 4-piperidone-3,5-dicarboxylates were synthesized by a Mannich procedure. Depending on the substitution at the nitrogen keto-enol-tautomerism and a configurational isomerism at C 2 is observed. The structure of the N-substituted piperidone 24 E (C18H29NO5) has been determined by X-ray analysis: it is characterized by an enol structure of the β-ketoester and an axial position of the alkyl group at C 2 and an equatorial one of the alkyl group at C 6. The O–H···O hydrogen bond shows characteristic values of a strong hydrogen bond. The N-unsubstituted piperidones

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3

K. Anuja and Nashwa K. K. "Innovative piperidone derivatives: a new horizon in Potent anticancer therapeutics." International Journal of Allied Medical Sciences and Clinical Research 12, no. 3 (2024): 354–62. https://doi.org/10.61096/ijamscr.v12.iss3.2024.354-362.

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Recent advancements in the synthesis and evaluation of piperidone derivatives have unveiled their remarkable potential as potent anticancer agents. This review highlights the innovative approaches and significant findings in the development of novel piperidone-based compounds, showcasing their efficacy against various cancer cell lines. Among the noteworthy compounds, dissymmetric 3,5-bis(arylidene)-4-piperidones (BAPs) have demonstrated selective cytotoxicity with minimal impact on normal cells. Further, modifications involving N-benzoylation, N-benzenesulfonylation and N-acryloylation have e

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4

Sartillo-Piscil, Fernando, Julio Romero-Ibañez, Silvano Cruz-Gregorio, and Leticia Quintero. "Concise and Environmentally Friendly Asymmetric Total Synthesis of the Putative Structure of a Biologically Active 3-Hydroxy-2-piperidone Alkaloid." Synthesis 50, no. 15 (2018): 2878–86. http://dx.doi.org/10.1055/s-0037-1610089.

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An asymmetric total synthesis of stereoisomers of a putative structure of 3-hydroxy-2-piperidone alkaloid derivative is described. This route is not only concise and efficient but also is achieved under an environmentally friendly approach. To this end, a direct and double C–H oxidation reaction of simple benzylated piperidine and Baker’s yeast reduction of a carbonyl group allowed the rapid access to the optically enriched (S)-1-benzyl-3-hydroxy-2-piperidone in only three steps. The NMR data agreed with those obtained in the first total synthesis (and in discrepancy with the natural product),

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5

Hieu, Truong Hong, Le Tuan Anh, Anatoly T. Soldatenkov, Nadezhda M. Kolyadina, and Victor N. Khrustalev. "Dimethyl 2-[24-acetyl-28-oxo-8,11,14-trioxa-24,27-diazapentacyclo[19.5.1.122,26.02,7.015,20]octacosa-2,4,6,15(20),16,18-hexaen-27-yl]but-2-enedioate." Acta Crystallographica Section E Structure Reports Online 68, no. 8 (2012): o2431—o2432. http://dx.doi.org/10.1107/s1600536812030644.

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The title compound, C31H34N2O9, is a product of the Michael addition of the cyclic secondary amine subunit of the (bispidino)aza-14-crown-4 ether to dimethyl acetylenedicarboxylate. The molecule comprises a tricyclic system containing the aza-14-crown-3 ether macrocycle and two six-membered piperidinone rings. The aza-14-crown-3-ether ring adopts a bowl conformation with a dihedral angle between the planes of the fused benzene rings of 51.14 (5)°. The central piperidone ring has a boat conformation, whereas the terminal piperidone ring adopts a chair conformation. The dimethyl ethylenedicarbox

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6

(MRS.), KR. MEENAL, and D. VIMALA DEVI (MRS.). "A Study of Conformational Effects on Oxidation Kinetics of N-H- and N-Methyl-4-piperidones with N-Bromosuccinimide : A Comparative Analysis." Journal of Indian Chemical Society Vol. 73, Aug 1996 (1996): 391–96. https://doi.org/10.5281/zenodo.5897413.

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Department of Chemistry, Seethalakshmi Ramaswami College (Autonomous), Trichy-620 002 <em>Manuscript received 26 March 1993, revised 25 October 1994, accepted 18 January 1995</em> A comparative oxidation kinetics of six pairs of<em> N</em>-H and .V-methyl-2,6-diphenyl-4-piperidones with <em>N</em>-bromosuccinimide (NBS) in aqueous acetic acid medium (20-80%, v/v) at constant ionic strength in presence or mercuric acetate has been investigated. The effect of alkyl substituents on the rates or oxidation in <em>N</em>-H series parallels their effects in <em>N</em>-H series. The enhanced rate

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7

Prisyazhnyuk, Vladimir, Matthias Jachan, Irene Brüdgam, Reinhold Zimmer та Hans-Ulrich Reissig. "Addition of lithiated methoxyallene to aziridines – a novel access to enantiopure piperidine and β-amino acid derivatives". Collection of Czechoslovak Chemical Communications 74, № 7-8 (2009): 1069–80. http://dx.doi.org/10.1135/cccc2009012.

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Addition of lithiated methoxyallene to aziridine derivatives provided the expected primary addition products. The less substituted carbon of the aziridine ring was attacked selectively. The primary adducts could be converted to enantiopure piperidine derivatives or β-amino acid derivatives. The unexpected reactions lead to a tricyclic sulfonamide and to alkynyl-substituted aminoethers. The efficient two-step conversion of a piperidone derivative to a benzomorphan demonstrates the potential of this approach to biologically active compounds.

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8

Méndez, Leonor, and Vladimir Kouznetsov. "Intramolecular N to N acyl migration in conformationally mobile 1′-acyl-1-benzyl-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-quinoline] systems promoted by debenzylation conditions (HCOONH4/Pd/C)." Open Chemistry 9, no. 5 (2011): 877–85. http://dx.doi.org/10.2478/s11532-011-0082-y.

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AbstractWe report an efficient and useful synthesis of new attractive spiropiperdine scaffolds 4 based on an intramolecular acyl transfer process in 1′-acyl-1-benzyl-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-quinolines] 3 using simple and mild debenzylation reaction conditions (HCOONH4/Pd/C). The compounds 3 were prepared by acylating 1-benzyl-4′-methyl-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-quinolines] 2 that are easily available from 1-benzyl-4-piperidone 1. The intramolecular character of this process was proven primarily through a crossover experiment technique. Through an examination of al

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9

Eryanti, Yum, Rudi Hendra, Tati Herlina, Adel Zamri, and Unang Supratman. "Synthesis of N-methyl-4-piperidone Curcumin Analogues and Their Cytotoxicity Activity against T47D Cell Lines." Indonesian Journal of Chemistry 18, no. 2 (2018): 362. http://dx.doi.org/10.22146/ijc.24174.

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Three piperidone curcumin analogues (N-methyl-(3E,5E)-3,5-bis-(2-chlorobenzylidene)-4-piperidone (1), N-methyl-(3E,5E)-3,5-bis-(3-bromobenzylidene)-4-piperidone (2) and N-methyl-(3E,5E)-3,5-bis-(4-chlorobenzylidene)-4-piperidone (3)) were synthesized from N-methyl-4-piperidone with halogenbenzaldehyde, 2-chlorobenzaldehyde, 3-bromobenzaldehyde and 4-chlorobenzaldehyde. The Claisen-Schmidt condensation reaction was used in alkali condition with combinatorial. All the compounds showed light yellow needle, light yellow powder, and yellow crystal form with percentage of yield 39, 66, and 40%, resp

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10

Li, Ning, Xianyong Bai, Lianshuang Zhang, and Yun Hou. "Synthesis, crystal structures and anti-inflammatory activity of four 3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidone derivatives." Acta Crystallographica Section C Structural Chemistry 74, no. 10 (2018): 1171–79. http://dx.doi.org/10.1107/s2053229618013232.

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3,5-Bis(arylidene)-4-piperidone (BAP) derivatives display good antitumour and anti-inflammatory activities because of their double α,β-unsaturated ketone structural characteristics. If N-benzenesulfonyl substituents are introduced into BAPs, the configuration of the BAPs would change significantly and their anti-inflammatory activities should improve. Four N-benzenesulfonyl BAPs, namely (3E,5E)-1-(4-methylbenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one dichloromethane monosolvate, C28H21F6NO3S·CH2Cl2, (4), (3E,5E)-1-(4-fluorobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)b

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11

Ivanović, Milovan, Ivana Jevtić, Ljiljana Došen-Mićović, Evica Ivanović, and Nina Todorović. "Synthesis of Orthogonally Protected (±)-3-Amino-4-anilidopiperidines and (±)-3-N-Carbomethoxyfentanyl." Synthesis 49, no. 14 (2017): 3126–36. http://dx.doi.org/10.1055/s-0036-1588985.

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The synthesis of orthogonally protected cis- and trans-3-amino-4-anilidopiperidine derivatives has been accomplished in six steps, starting from readily accessible 4-piperidone derivatives. The last three steps, i.e., N-acylation, Hofmann rearrangement, and carbamate cleavage, involved separated (±)-cis and (±)-trans intermediates. Complete retention of configuration was observed at position 3 of the piperidine ring. Specifically protected positions 1 and 3 at the piperidine scaffold allow for selective deprotection and introduction of diverse substituents at the respective nitrogen sites. The

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12

Habibi, Romi, Noval Herfindo, Rudi Hendra, Hilwan Y. Teruna, and Adel Zamri. "Synthesis and Molecular Docking Study of 1-(3-Chloropropyl)-3,5-Bis((E)-4-Methoxybenzylidene)Piperidin-4-One as Dengue Virus Type 2 (DEN2) NS2B/NS3 Protease Inhibitor Candidate." Pharmacology and Clinical Pharmacy Research 5, no. 1 (2020): 14. http://dx.doi.org/10.15416/pcpr.v5i1.25624.

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Curcumin is a secondary metabolite compound that has diverse biological activities. However, it is easily hydrolyzed at physiological pH due to the presence of the β-diketone group. Therefore, the replacement of the β-diketone group with mono ketone is expected to overcome this issue. We hereby report the synthesis of mono ketone curcumin derivatives from piperidone by two-steps reactions. The synthesis of curcumin derivate 3 was carried out by Claisen-Schmidt condensation between 4-piperidone and 4-methoxybenzaldehyde using alkaline catalyst. The synthesized curcumin derivate 3 was then react

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13

Šindelář, Karel, Jiří Holubek, Jiří Schlanger, Antonín Dlabač, Martin Valchář, and Miroslav Protiva. "Synthesis of spiro(piperidine-4,6'-dibenz[b,e]-1,4-oxathiepin) and its 1-methyl derivative as potential antidepressant agents." Collection of Czechoslovak Chemical Communications 50, no. 2 (1985): 503–9. http://dx.doi.org/10.1135/cccc19850503.

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Starting from 2-chloronitrobenzene and 2-fluorothiophenol, the synthesis of 2-bromo-2'-fluorodiphenyl sulfide (X) was carried out in three steps. The product was converted to the Grignard reagent which reacted with 1-ethoxycarbonyl-4-piperidone and gave the alcohol XIII. Cyclization of this compound with sodium hydride in dimethylformamide afforded 1-ethoxycarbonylspiro(piperidine-4,6'-dibenz[b,e]-1,4-oxathiepin) (V) which was hydrolyzed to the title compound IV. Reduction of compound V with sodium dihydridobis(2-methoxyethoxy)aluminate afforded the 1-methyl derivative III which exhibited anti

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14

Rajkumar, K., S. Sivakumar, R. Arulraj, et al. "Crystal structures of two new 3-(2-chloroethyl)-r(2),c(6)-diarylpiperidin-4-ones." Acta Crystallographica Section E Crystallographic Communications 74, no. 4 (2018): 483–86. http://dx.doi.org/10.1107/s2056989018003766.

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The syntheses and crystal structures of 3-(2-chloroethyl)-r-2,c-6-diphenylpiperidin-4-one, C19H20ClNO, (I), and 3-(2-chloroethyl)-r-2,c-6-bis(4-fluorophenyl)piperidin-4-one, C19H18ClF2NO, (II), are described. The piperidone ring adopts a chair conformation in (I), whereas a slightly distorted chair conformation is formed in (II). The dihedral angle between the mean plane of the phenyl rings is 59.1 (1)° in (I) and 76.1 (1)° in (II). The crystal packing features weak intermolecular N—H...O hydrogen bonds in each structure.

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15

Shanmugam Nagarajan, N., R. Priya Rao, C. Narayanan Manoj, and M. Gopalakrishnan Sethuraman. "Piperidone derivative fromDalbergia sympathetica." Magnetic Resonance in Chemistry 43, no. 3 (2005): 264–65. http://dx.doi.org/10.1002/mrc.1516.

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16

Sekar, K., S. Parthasarathy, and P. Rajalingam. "Structure of 4-piperidone derivatives. I. 3-Methyl-2,6-diphenyl-4-piperidone." Acta Crystallographica Section C Crystal Structure Communications 46, no. 6 (1990): 1153–55. http://dx.doi.org/10.1107/s0108270190000786.

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17

Aisyah, Siti, Adel Zamri, and Hilwan Yuda Teruna. "SINTESIS DAN UJI TOKSISITAS SENYAWA ANALOG KURKUMIN 3,5 BIS((E)-METOKSI BENZILIDEN)-1-(2-ETIL ASETAT)-PIPERIDIN-4-ON." Photon: Jurnal Sain dan Kesehatan 9, no. 1 (2018): 159–63. http://dx.doi.org/10.37859/jp.v9i1.1075.

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Curcumin analogs are secondary metabolites and belong to the phenolic group. These compounds have biological activities, such as anti-inflammatory, anticancer and antioxidant. This studies has successfully synthesized 3,5-bis ((E)-metoxy benzylidene) -1-(- 2-ethyl acetate) piperidine 4-one analog compound from 4-piperidone with 4-methoxy benzaldehyde by using reflux method. Compounds obtained in the form of yellow solids with yield 83.01%. The melting point was measured, identified by TLC then elucidated with UV-Vis, FT-IR, LC-MS, 1H NMR obtained results showed that the curcumin compound had a

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18

Neganova, M. E., Yu R. Aleksandrova, E. V. Sharova, et al. "Conjugates of 3,5-Bis(arylidene)-4-piperidone and Sesquiterpene Lactones Have an Antitumor Effect via Resetting the Metabolic Phenotype of Cancer Cells." Molecules 29, no. 12 (2024): 2765. http://dx.doi.org/10.3390/molecules29122765.

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In recent years, researchers have often encountered the significance of the aberrant metabolism of tumor cells in the pathogenesis of malignant neoplasms. This phenomenon, known as the Warburg effect, provides a number of advantages in the survival of neoplastic cells, and its application is considered a potential strategy in the search for antitumor agents. With the aim of developing a promising platform for designing antitumor therapeutics, we synthesized a library of conjugates of 3,5-bis(arylidene)-4-piperidone and sesquiterpene lactones. To gain insight into the determinants of the biolog

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19

Sekar, K., S. Parthasarathy, and T. R. Radhakrishnan. "Structure of 4-piperidone derivatives. III. 1,3,3-Trimethyl-2,6-diphenyl-4-piperidone and 2,6-bis(p-chlorophenyl)-1,3,5-trimethyl-4-piperidone." Acta Crystallographica Section C Crystal Structure Communications 49, no. 1 (1993): 93–95. http://dx.doi.org/10.1107/s0108270192004207.

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20

Rahmawati, E. N., H. Y. Teruna, and A. Zhamri. "SINTESIS DAN UJI TOKSISITAS SENYAWA ANALOG KURKUMIN 3,5-BIS((E)-METOKSI BENZILIDEN)-1-(FENILSULFONIL)-PIPERIDIN-4-ON." Photon: Jurnal Sain dan Kesehatan 9, no. 1 (2018): 151–58. http://dx.doi.org/10.37859/jp.v9i1.1074.

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A study has been conducted to synthesize analog of curcumin with base catalyzed condensation of 4-piperidone hydrochloride with substituted benzaldehyde under reflux led the formation of mono-carbonyl curcumin. The synthesized curcumin were further reacted with benzosulphonyl chloride by nucleophilic substitution of –NH group to afford 3,5-bis((E)-2-metoksi benziliden)-1-(fenilsulfonil)piperidin-4-on (EN-BS) compounds with excellent yield, 94%. Structure of the synthesized compounds were confirmed by UV, IR, MS and NMR spectra analysis. All the synthesized compounds were screened for their tox

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21

Klegraf, Ellen, and Horst Kunz. "Stereoselective Synthesis of 3-Substituted and 3,4-Disubstituted Piperidine und Piperidin-2-one Derivatives." Zeitschrift für Naturforschung B 67, no. 4 (2012): 389–405. http://dx.doi.org/10.1515/znb-2012-0413.

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The stereoselective synthesis of 3-substituted and 3,4-disubstituted piperidine and piperidin-2-one derivatives was achieved starting from 2-pyridone. After N-galactosylation and subsequent O-silylation, nucleophilic addition of organometallic reagents proceeded with high regio- and stereoselectivity at 4-position. Substituents at position 3 were stereoselectively introduced by reaction of electrophiles with amide enolates of the N-galactosyl-2-piperidones.

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22

Šilhánková, Alexandra, Karel Šindelář, Karel Dobrovský, Ivan Krejčí, Jarmila Hodková, and Zdeněk Polívka. "Synthesis of New L-Proline Amides with Anticonvulsive Effect." Collection of Czechoslovak Chemical Communications 61, no. 7 (1996): 1085–92. http://dx.doi.org/10.1135/cccc19961085.

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Series of heterocyclic L-proline amides were prepared from BOC-L-proline and heterocyclic amines (mostly substituted piperazines and morpholines) via active ester with hydroxysuccinimide. 4-(4-Fluorobenzoyl)piperidine afforded L-proline 4-(4-(4-(4-fluorobenzoyl)piperidin-1-yl)benzoyl)piperidine (7b) simultaneously with expected L-proline 4-(4-fluorobenzoyl)piperidide (7a). D-Proline N-(3-(4-(3-chlorophenyl)piperazin-1-yl)propyl)amide (2) was prepared starting from D-proline. The amides were tested by methods of biochemical and behavioural pharmacology.

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23

(MRS.), KR. MEENAL, and G. RAMANI VIMALA (MRS.). "Correlation Analysis of Reactivity in the Oxidation of 3,5- Dimethyl-2,6-diaryl-4-piperidones by Peroxomonosulphate." Journal of Indian Chemical Society Vol. 71, Oct 1994 (1994): 609–11. https://doi.org/10.5281/zenodo.5896659.

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Department of Chemistry, Seethalakshmi Ramaswami College (Autonomous), Trichy-620 002 <em>Manuscript received 7 April 1993, accepted 17 August 1993</em> Kinetics of oxidation of 3,5-dimethyl-2,6-(diphenylldi-p-tolyl/di-p-anisylldi-p-chlorophenyl/di-p-nitrophenyl)·4-piperidones by peroxomonosulphate in aqueous acetic acid medium have been studied. The reactions are first order, both in the piperidone and in the oxidant. Electron-withdrawing groups are found to accelerate the rate of oxidation and the electron-releasing groups retard it. The Hammett <em>p</em>\(\sigma\) relationship is us

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24

Sekar, K., S. Parthasarathy, and T. R. Radhakrishnan. "Structure of 4-piperidone derivatives. II. 2,6-Bis(p-methoxyphenyl)-3,5-dimethyl-4-piperidone." Acta Crystallographica Section C Crystal Structure Communications 46, no. 7 (1990): 1338–40. http://dx.doi.org/10.1107/s0108270190002220.

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25

Girgis, Adel S., Padraig D'Arcy, Dalia R. Aboshouk, and Mohamed S. Bekheit. "Synthesis and bio-properties of 4-piperidone containing compounds as curcumin mimics." RSC Advances 12, no. 48 (2022): 31102–23. http://dx.doi.org/10.1039/d2ra05518j.

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26

Lei, Yu, Boao Li, Xiaojian Liao, et al. "Isolation and total synthesis of dysidone A: a new piperidone alkaloid from the marine sponge Dysidea sp." RSC Advances 13, no. 42 (2023): 29316–19. http://dx.doi.org/10.1039/d3ra06115a.

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A., Rajasekaran, and Murugesan S. "Synthesis and antimicrobial evaluation of thiosemicarbazones." Journal of Indian Chemical Society Vol. 79, Jun 2002 (2002): 544–45. https://doi.org/10.5281/zenodo.5844225.

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Arulmigu Kalasalingam College of Pharmacy, Anand Nagar, Krishnankoil-626 190, India <em>Manuscript received 11 July 2001. accepted 25 September 2001</em> Some new thiosemicarbazones (2-7) have been synthesized via condensation of piperidone 1, thisemicarbazide and some acylating agents. Majority of the compounds showed significant antimicrobial activity.

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Puet, Alejandro, Gema Domínguez, Francisco Javier Cañada, and Javier Pérez-Castells. "Synthesis and Evaluation of Novel Iminosugars Prepared from Natural Amino Acids." Molecules 26, no. 2 (2021): 394. http://dx.doi.org/10.3390/molecules26020394.

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Cyclopropanated iminosugars have a locked conformation that may enhance the inhibitory activity and selectivity against different glycosidases. We show the synthesis of new cyclopropane-containing piperidines bearing five stereogenic centers from natural amino acids l-serine and l-alanine. Those prepared from the latter amino acid may mimic l-fucose, a natural-occurring monosaccharide involved in many molecular recognition events. Final compounds prepared from l-serine bear S configurations on the C5 position. The synthesis involved a stereoselective cyclopropanation reaction of an α,β-unsatur

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29

Grishina, G. V., and E. L. Gaidarova. "Highly enantioselective synthesis of 3,3-disubstituted 4-piperidones by michael alkylation of chiral piperidone imines." Chemistry of Heterocyclic Compounds 28, no. 8 (1992): 898–904. http://dx.doi.org/10.1007/bf00531322.

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Jevtic, Ivana, Jelena Penjisevic, Milovan Ivanovic, and Sladjana Kostic-Rajacic. "Synthetic route towards potential bivalent ligands possessing opioid and D2/D3 pharmacophores." Journal of the Serbian Chemical Society 84, no. 7 (2019): 639–47. http://dx.doi.org/10.2298/jsc181002105j.

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A scalable, cost-efficient and simple synthetic pathway towards potential bivalent opioid/dopamine receptor ligands was developed and optimized. Three novel compounds that contain both opioid and dopamine pharmacophores linked by the four methylene group chain were synthesized in 33, 35 and 39 % overall yield after a four-step synthetic route starting from three commercially available N-aryl piperazines. The anilino piperidine precursor was easily prepared in three steps, as previously published, starting from 4- piperidone. The synthesis presented in this paper could be of interest for hetero

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Kiricojevic, Vesna, Milovan Ivanovic, I. V. Micovic, J. B. Djordjevic, Goran Roglic, and Ljiljana Dosen-Micovic. "An optimized synthesis of a key pharmaceutical intermediate methyl 4-[(1-oxopropyl)phenylamino]piperidine-4-carboxylate." Journal of the Serbian Chemical Society 67, no. 12 (2002): 793–802. http://dx.doi.org/10.2298/jsc0212793k.

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An efficient synthesis of methyl 4-[(1-oxopropyl)phenylamino]piperidine-4-carboxylate (7) has been developed starting from 1-benzylpiperidin-4-one (1). The compound is a key intermediate in the synthesis of new generation, highly active narcotic analgesics, such as remifintanil, as well as the novel classes of fentanyl analogues. An optimized Strecker-type condensation of piperidone 1 with aniline and HCN yielded the anilino-nitrile 2(?90%) which, upon selective hydrolysis with conc. H2SO4, gave the anilino-amide 3.After vigorous basic hydrolysis of 3, followed by acidification and successive

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Singh, P., S. G. Levine, and K. Kasdorf. "Structure of 2,6-diphenyl-4-piperidone." Acta Crystallographica Section C Crystal Structure Communications 46, no. 12 (1990): 2469–70. http://dx.doi.org/10.1107/s0108270190004644.

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33

Zukerman-Schpector, Julio, Paulo R. Olivato, Carlos R. Cerqueira Jr, Elisângela Vinhato, and Edward R. T. Tiekink. "1-Methyl-3-phenylsulfonyl-2-piperidone." Acta Crystallographica Section E Structure Reports Online 64, no. 5 (2008): o835—o836. http://dx.doi.org/10.1107/s1600536808009288.

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34

Winkler, Tammo. "Comments on ‘Piperidone derivative fromDalbergia sympathetica’." Magnetic Resonance in Chemistry 44, no. 5 (2006): 571–72. http://dx.doi.org/10.1002/mrc.1783.

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35

Kim, You-Ri, and Dennis G. Hall. "Optimization and multigram scalability of a catalytic enantioselective borylative migration for the synthesis of functionalized chiral piperidines." Organic & Biomolecular Chemistry 14, no. 20 (2016): 4739–48. http://dx.doi.org/10.1039/c6ob00685j.

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36

Toumi, Amani, Sarra Boudriga, Yasmine M. Mandour, et al. "Design of Novel Enantiopure Dispirooxindolopyrrolidine-Piperidones as Promising Candidates toward COVID-19: Asymmetric Synthesis, Crystal Structure and In Silico Studies." Molecules 27, no. 12 (2022): 3945. http://dx.doi.org/10.3390/molecules27123945.

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Despite the effectiveness of COVID-19 vaccines, there is still an urgent need for discovering new anti-viral drugs to address the awful spread and transmission of the rapidly modifiable virus. In this study, the ability of a small library of enantiomerically pure spirooxindolopyrrolidine-grafted piperidones to inhibit the main protease of SARS-CoV-2 (Mpro) is evaluated. These spiroheterocycles were synthesized by 1,3-dipolar cycloaddition of various stabilized azomethine ylides with chiral dipolarophiles derived from N-[(S)-(-)-methylbenzyl]-4-piperidone. The absolute configuration of contiguo

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37

Jílek, Jiří, Miroslav Rajšner, Vladimír Valenta, et al. "Synthesis of piperidine derivatives as potential analgetic agents." Collection of Czechoslovak Chemical Communications 55, no. 7 (1990): 1828–53. http://dx.doi.org/10.1135/cccc19901828.

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Reaction of N-(1-(2-phenylethyl)-4-piperidinyl)propionanilide (I) with phosphorus pentasulfide gave the thioamide VI. Acylation of N-(1-(2-phenylethyl)-4-piperidinyl)aniline with 2-(methoxy)acetic and 2-(methylthio)acetic anhydrides afforded the amides II and III. Treatment of 4-anilino-1-benzylpiperidine-4-methanol with thionyl chloride gave the spirocyclic sulfurous acid ester amide XIV. Reduction of the hydrochloride of ethyl 3-(1-ethoxycarbonyl-4-phenylimino-3-piperidinyl)propionate (XXII) with sodium cyanoborohydride gave the perhydro-1,6-naphthyridine derivative XIX, a model compound in

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38

Thakur, Anuj, Sunny Manohar, Christian E. Vélez Gerena, et al. "Novel 3,5-bis(arylidiene)-4-piperidone based monocarbonyl analogs of curcumin: anticancer activity evaluation and mode of action study." Med. Chem. Commun. 5, no. 5 (2014): 576–86. http://dx.doi.org/10.1039/c3md00399j.

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39

Nesterov, Vladimir N., Tatiana V. Timofeeva, Sergey S. Sarkisov, Alexander Leyderman, Charles Y. C. Lee, and Mikhail Yu Antipin. "3,5-Bis[4-(diethylamino)benzylidene]-1-methyl-4-piperidone and 3,5-bis[4-(diethylamino)cinnamylidene]-1-methyl-4-piperidone: prospective biophotonic materials." Acta Crystallographica Section C Crystal Structure Communications 59, no. 11 (2003): o605—o608. http://dx.doi.org/10.1107/s0108270103020237.

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The structures of 3,5-bis[4-(diethylamino)benzylidene]-1-methyl-4-piperidone, C28H37N3O, (I), and 3,5-bis[4-(diethylamino)cinnamylidene]-1-methyl-4-piperidone, C32H41N3O, (II), have been characterized. Because of conjugation between donor and acceptor parts, the central heterocycles (including the carbonyl group) in (I) and (II) are flattened and exhibit a `sofa' conformation, with a deviation of the N atom from the planar fragment. The dihedral angles between the planar part of the heterocycle and the two almost flat fragments that include a phenyl ring and bridging atoms are 23.2 (1) and 11.

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40

Caracelli, Ignez, Paulo R. Olivato, Carlos R. Cerqueira Jr, Jean M. M. Santos, Seik Weng Ng, and Edward R. T. Tiekink. "1-Methyl-3,3-bis(phenylsulfanyl)piperidin-2-one." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (2012): o1793—o1794. http://dx.doi.org/10.1107/s1600536812021277.

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The piperidone ring in the title compound, C18H19NOS2, is in a distorted half-chair conformation, distorted towards a twisted boat, with the central methylene C atom of the propyl backbone lying 0.606 (2) Å out of the plane defined by the other five atoms (r.m.s. deviation = 0.1197 Å). One of the S-bound phenyl rings is almost perpendicular to the least-squares plane through the piperidone ring, whereas the other is splayed [dihedral angles = 75.97 (6) and 44.21 (7)°, respectively]. The most prominent feature of the crystal packing is the formation of helical supramolecular chains along the b

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41

Tiwari, Anil K., Abha Bishnoi, Anil Kumar Verma, et al. "Synthesis, characterization, and antimicrobial evaluation of novel spiropiperidones." Heterocyclic Communications 21, no. 4 (2015): 239–43. http://dx.doi.org/10.1515/hc-2015-0075.

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AbstractNovel spiro derivatives of piperidone 4a–f were synthesized, characterized, and screened against a panel of different bacterial and fungal strains. The study revealed the potential of these molecules for further development as antimicrobial agents.

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42

Mamillapalli, Vani, Abdul Rahaman Shaik, and Prameela Rani Avula. "Hepatoprotective activity of 2-piperidone isolated from leaf extracts of Talinum portulacifolium (Forssk.) Asch. ex Schweinf in carbon tetrachloride induced hepatotoxicity." Journal of Pharmacy & Pharmacognosy Research 7, no. 1 (2019): 234–45. http://dx.doi.org/10.56499/jppres18.489_7.4.234.

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Context: Liver disorders have become a common problem worldwide. The drugs available currently for the treatment are few with serious side effects. Since phytochemicals have proven to be potential therapeutic agents, an attempt has been made to screen novel hepatoprotective agents from the leaves of the medicinally ignored plant Talinum portulacifolium. Aims: To evaluate the phytoconstituents of Talinum portulacifolium responsible for hepatoprotective activity in carbon tetrachloride-induced hepatotoxicity models both in vitro and in vivo. Methods: The hepatic damage was assessed in vitro by s

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43

Amalraj, John, Claudia E. Vergara, Matías Monroy-Cárdenas, Ramiro Araya-Maturana, and Maximiliano Martínez-Cifuentes. "Study of the Electrochemical Behavior of N-Substituted-4-Piperidones Curcumin Analogs: A Combined Experimental and Theoretical Approach." International Journal of Molecular Sciences 23, no. 23 (2022): 15043. http://dx.doi.org/10.3390/ijms232315043.

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The electrochemical behavior of N-methyl- and N-benzyl-4-piperidone curcumin analogs were studied experimentally and theoretically. The studied compounds present different substituents at the para position in the phenyl rings (-H, -Br, -Cl, -CF3, and -OCH3). We assessed their electrochemical behavior by differential pulse and cyclic voltammetry, while we employed density functional theory (DFT) M06 and M06-2x functionals along with 6-311+G(d,p) basis set calculations to study them theoretically. The results showed that compounds suffer a two-electron irreversible oxidation in the range of 0.72

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44

Cooling, F. B., S. K. Fager, R. D. Fallon, et al. "Chemoenzymatic production of 1,5-dimethyl-2-piperidone." Journal of Molecular Catalysis B: Enzymatic 11, no. 4-6 (2001): 295–306. http://dx.doi.org/10.1016/s1381-1177(00)00150-8.

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45

Roayapalley, Praveen K., Jonathan R. Dimmock, Lisett Contreras, et al. "Design, Synthesis and Tumour-Selective Toxicity of Novel 1-[3-{3,5-Bis(benzylidene)-4-oxo-1-piperidino}-3-oxopropyl]-4-piperidone Oximes and Related Quaternary Ammonium Salts." Molecules 26, no. 23 (2021): 7132. http://dx.doi.org/10.3390/molecules26237132.

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A novel series of 1-[3-{3,5-bis(benzylidene)-4-oxo-1-piperidino}-3-oxopropyl]-4-piperidone oximes 3a–h and related quaternary ammonium salts 4a–h were prepared as candidate antineoplastic agents. Evaluation against neoplastic Ca9-22, HSC-2 and HSC-4 cells revealed the compounds in series 3 and 4 to be potent cytotoxins with submicromolar CC50 values in virtually all cases. In contrast, the compounds were less cytocidal towards HGF, HPLF and HPC non-malignant cells revealing their tumour-selective toxicity. Quantitative structure–activity relationships revealed that, in general, both cytotoxic

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46

Díaz-Uribe, Carlos Enrique, William Andrés Vallejo-Lozada, and Fernando Martínez-Ortega. "Photooxidation of anthracene under visible light with metallocarboxyphenylporphyrins." Revista Facultad de Ingeniería Universidad de Antioquia, no. 73 (November 13, 2014): 225–30. http://dx.doi.org/10.17533/udea.redin.17273.

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In this work, three novel carboxyphenylporphyrins (TcPP-M, M= H, Cu y Zn) have been synthesized and their efficiency in the photooxidation of anthracene under visible light (l> 500 nm) through generation of oxygen singlet (1O2) has been evaluated. The presence of 1O2 was evidenced by Electron Paramagnetic Resonance (EPR), where it reacts with 2,2,6,6-tetramethyl-4-piperidone-N (TEMP) to produce 2,2,6,6-tetramethyl-4-piperidone-N-oxyl radical (TEMPO). The catalytic results indicated that the incorporation of the metal in the porphyrin ring strongly affects their efficiency on the anthracene

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47

Mishra, Shweta, Debashree Das, Adarsh Sahu, Shailendra Patil, Ram Kishore Agrawal, and Asmita Gajbhiye. "Phosphonate Derivatives of 3,5-bis(arylidene)-4-piperidone: Synthesis and Biological Evaluation." Anti-Infective Agents 18, no. 3 (2020): 245–54. http://dx.doi.org/10.2174/2211352517666190820143735.

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Background: 3,5-Bis(arylidene)-4-piperidinones (BAP) belong to a wide class of cross conjugated dienones. The 1,5-diaryl-3-oxo-1,4-pentadienyl fragment of the BAP moiety is responsible for the molecule's anti-tumor, antioxidant, antimicrobial and anti-inflammatory manifestations. In the present study, we present combinations of phosphonate and 3,5-bis(arylidene)-4- piperidone pharmacophores. The anti-inflammatory, anti-oxidant potential, anti-proliferative, cytotoxic potential and antimicrobial of the title compounds were evaluated in in-vitro bioassay paradigms. Methods: A novel class of phos

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48

K, Manjusha R., Shaheen Begum, Arifa Begum, and Bharathi K. "ANTIOXIDANT POTENTIAL OF PIPERIDINE CONTAINING COMPOUNDS-A SHORT REVIEW." Asian Journal of Pharmaceutical and Clinical Research 11, no. 8 (2018): 66. http://dx.doi.org/10.22159/ajpcr.2018.v11i8.26536.

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Piperidine is a saturated heterocyclic ring, considered as a privileged scaffold in view of its role in wide range of biological activities. Piperidine is good candidate molecule for obtaining potent antioxidant agents. The planar nature of this heterocyclic nucleus allows the introduction of substituent groups at different positions on the ring. In the present review, the antioxidant profile of piperidine containing compounds has been focused. The compounds were classified into naturally occurring piperidines, unsaturated piperidines, N-substituted piperidines, piperamides, piperanols, piperi

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49

Lagisetty, Pallavi, Hrushikesh Agashe, and Vibhudutta Awasthi. "2-[3,5-Bis-(2-fluorobenzylidene)-4-piperidon-1-yl]-N-(4-fluorobenzyl)-acetamide and Its Evaluation as an Anticancer Agent." Journal of Chemistry 2013 (2013): 1–9. http://dx.doi.org/10.1155/2013/935646.

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Synthesis of 2-[3,5-bis-(2-fluorobenzylidene)-4-piperidon-1-yl]-N-(4-fluorobenzyl)-acetamide, a derivative of 3,5-bis-(2-fluorobenzylidene)-4-piperidone (EF24), as an antiproliferative and imageable compound is described. The radioactive derivative was synthesized in 40–45% radiochemical yield using N-[4-fluoro(18F)benzyl]-2-bromoacetamide (NFLOBA) as a radiolabeled synthon for coupling with EF24. Cell proliferation assays showed that 2-[3,5-bis-(2-fluorobenzylidene)-4-piperidon-1-yl]-N-(4-fluorobenzyl)-acetamide (NFLOBA-EF24) had antiproliferative efficacy similar to that of EF24 in lung aden

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50

Grishina, G. V., V. M. Potapov, T. A. Gudasheva, and S. A. Abdulganeeva. "First asymmetric synthesis of 4-piperidones. Preparation of optically active diastereomers of 1-?-phenylethyl-2-methyl-4-piperidone." Chemistry of Heterocyclic Compounds 21, no. 10 (1985): 1132–36. http://dx.doi.org/10.1007/bf00515253.

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