23434-88-0Relevant academic research and scientific papers
Amides from Piper capense with CNS activity - A preliminary SAR analysis
Pedersen, Mikael E.,Metzler, Bjorn,Stafford, Gary I.,Van Staden, Johannes,Jaeger, Anna K.,Rasmussen, Hasse B.
, p. 3833 - 3843 (2009)
Piper capense L.f. (Piperaceae) is used traditionally in South Africa as a sleep inducing remedy. Bioassay-guided fractionation of the roots of P. capense led to the isolation of piperine (1) and 4,5-dihydropiperine (2), which showed moderate affinity for the benzodiazepine site on the GABAA receptor (IC50 values of 1.2 mM and 1.0 mM, respectively). The present study suggests that strict structural properties of the amides are essential for affinity. Taken together, these observations suggest that the carbon chain must contain not less than four carbons, and that a conjugated double bond, adjacent to the amide group, is necessary for binding to the receptor and that the amine part should be bulky.
Regioselective reduction of the α, β - double bond of some naturally occurring dienamides using NaBH4/I2 system
Das, Biswanath,Kashinatham,Madhusudhan
, p. 677 - 678 (1998)
The regioselective reduction of the α, β - double bond of the naturally occurring dienamides, piperine, piperlonguminine and N - isobutyl - 2E, 4E - decadienamide was achieved by using NaBH4/I2 system.
Highly Selective Hydrogenation of C═C Bonds Catalyzed by a Rhodium Hydride
Gu, Yiting,Lisnyak, Vladislav G.,Norton, Jack R.,Salahi, Farbod,Snyder, Scott A.,Zhou, Zhiyao
supporting information, p. 9657 - 9663 (2021/07/19)
Under mild conditions (room temperature, 80 psi of H2) Cp*Rh(2-(2-pyridyl)phenyl)H catalyzes the selective hydrogenation of the C═C bond in α,β-unsaturated carbonyl compounds, including natural product precursors with bulky substituents in the β position and substrates possessing an array of additional functional groups. It also catalyzes the hydrogenation of many isolated double bonds. Mechanistic studies reveal that no radical intermediates are involved, and the catalyst appears to be homogeneous, thereby affording important complementarity to existing protocols for similar hydrogenation processes.
PROCESS FOR THE PREPARATION OF PIPERINE
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Page/Page column 9; 15, (2019/05/02)
The present application relates to a process for the preparation of piperine of high purity having low concentrations of isomeric impurities.
Fragmentation pattern of amides by EI and HRESI: Study of protonation sites using DFT-3LYP data
Fokoue,Marques,Correia,Yamaguchi,Qu,Aires-De-Sousa,Scotti,Lopes,Kato
, p. 21407 - 21413 (2018/06/26)
Amides are important natural products which occur in a few plant families. Piplartine and piperine, major amides in Piper tuberculatum and P. nigrum, respectively, have shown a typical N-CO cleavage when analyzed by EI-MS or HRESI-MS. In this study several synthetic analogs of piplartine and piperine were subjected to both types of mass spectrometric analysis in order to identify structural features influencing fragmentation. Most of the amides showed an intense signal of the protonated molecule [M + H]+ when subjected to both HRESI-MS and EI-MS conditions, with a common outcome being the cleavage of the amide bond (N-CO). This results in the loss of the neutral amine or lactam and the formation of aryl acylium cations. The mechanism of N-CO bond cleavage persists in α,β-unsaturated amides because of the stability caused by extended conjugation. Computational methods determined that the protonation of the piperamides and their derivatives takes place preferentially at the amide nitrogen supporting the dominant the N-CO bond cleavage.
Synthesis and inhibitory effect of piperine derivates on monoamine oxidase
Mu, Li-Hua,Wang, Bo,Ren, Hao-Yang,Liu, Ping,Guo, Dai-Hong,Wang, Fu-Meng,Bai, Lin,Guo, Yan-Shen
scheme or table, p. 3343 - 3348 (2012/06/29)
A series of piperine derivates (1-19) have been designed, synthesized and evaluated in vitro for their monoamine oxidase (MAO) A and B inhibitory activity and selectivity. It is worth noting that most of the small amine moieties substituted on the piperidine ring proved to be potent and selective inhibitors of MAO-B rather than of MAO-A. 5-(3,4-methylenedioxyphenyl)-2E,4E-pentadienoic acid n-propyl amide (3) showed the greatest MAO-B inhibitory activity (IC 50(MAO-B) = 0.045 μM) and good selectivity (IC50(MAO-A) = 3.66 μM). The conjugated double bond and carbonyl group of piperine are proved to be an essential feature for piperine and related alkylamides to exhibit MAO-inhibitory activity. Binding mode of the titled compounds was predicted using FlexX algorithm. The design and optimization of novel small molecule monoamine oxidase inhibitors will be guided by the results of this report.
In vitro TRPV1 activity of piperine derived amides
Correa, Edwin Andrés,H?gest?tt, Edward D.,Sterner, Olov,Echeverri, Fernando,Zygmunt, Peter M.
experimental part, p. 3299 - 3306 (2010/07/04)
A series of natural and synthetic piperine amides were evaluated for activity on the human TRPV1 expressed in HEK293 cells. The agonistic effect of piperine amides was mainly dependent on the length of the carbon chain. Structural changes of double bonds and stereochemistry in the aliphatic chain of these compounds did not change their potency or efficacy, indicating that increased rigidity or planarity of the piperine structure does not affect the activity. The opening of the methylenedioxy ring or changes in the heterocyclic ring of the piperine molecule reduced or abolished activity. Furthermore, inactive compounds did not display functional antagonistic activity.
Piperine analogs as potent Staphylococcus aureus NorA efflux pump inhibitors
Sangwan, Payare L.,Koul, Jawahir L.,Koul, Surrinder,Reddy, Mallepally V.,Thota, Niranjan,Khan, Inshad A.,Kumar, Ashwani,Kalia, Nitin P.,Qazi, Ghulam N.
experimental part, p. 9847 - 9857 (2009/04/11)
Based on our recent findings that piperine is a potent Staphylococcus aureus NorA efflux pump inhibitor (EPI), 38 piperine analogs were synthesized and bioevaluated for their EPI activity. Twenty-five of them were found active with potentiating activity equivalent or more than known EPIs like reserpine, carsonic acid and verapamil. The inhibitory mechanism of the compounds was confirmed by efflux inhibition assay using ethidium bromide as NorA substrate. The present communication describes the synthesis, bioevaluation and structure related activity of these efflux pump inhibitors.
Toxic effects of natural piperine and its derivatives on epimastigotes and amastigotes of Trypanosoma cruzi
Ribeiro, Tatiana Santana,Freire-De-Lima, Leonardo,Previato, Jose Osvaldo,Mendonca-Previato, Lucia,Heise, Norton,De Lima, Marco Edilson Freire
, p. 3555 - 3558 (2007/10/03)
We describe herein an evaluation of trypanocidal effects of the natural alkaloid piperine and twelve synthetic derivatives against epimastigote and amastigote forms of the protozoan parasite Trypanosoma cruzi, the causative agent of the incurable human disease, Chagas' disease. The results obtained point to piperine as a suitable template for the development of new drugs with trypanocidal activity.
Effects of piperine analogues on stimulation of melanocyte proliferation and melanocyte differentiation
Venkatasamy, Radhakrishnan,Faas, Laura,Young, Antony R.,Raman, Amala,Hider, Robert C.
, p. 1905 - 1920 (2007/10/03)
A wide range of piperine analogues has been synthesised in order to undertake a structure-activity study of their ability to stimulate melanocyte proliferation. Results demonstrate that an aromatic ring containing at least one ether function and a carbonyl group containing side chain is essential for this activity. A number of highly active piperine analogues have been identified, for instance 1-(3,4-methylenedioxyphenyl)-penta-2E,4E-dienoic acid methyl ester (5a), 1-E,E-piperinoyl-isobutylamine (4f) and 1-(3,4- methylenedioxyphenyl)-pentanoic acid cyclohexyl amide (20). A selection of analogues has also been evaluated for their effect on melanocyte morphology and melanogenesis. The piperine analogues altered cell morphology by increasing dendrite formation leading to bi-, tri- and quadripolar cells. These same analogues were found to increase total melanin in cell cultures, although melanin content per cell was not significantly altered from control in the presence of these compounds.
