5950-12-9 Usage
Description
Piperlonguminine is an alkaloid amide derived from the Piper genus, a plant utilized in traditional medicine. piperlonguminine exhibits a range of pharmacological properties, including antifungal, anticancer, antihyperlipidemic, and anti-inflammatory activities. Piperlonguminine is characterized by its doubly unsaturated side chain, which upon catalytic hydrogenation, yields a tetrahydro derivative with a melting point of 66°C. piperlonguminine also demonstrates absorption maxima at 245, 256, 307, and 340 mil in the ultraviolet spectrum.
Uses
Used in Pharmaceutical Applications:
Piperlonguminine is used as a therapeutic agent for its diverse medicinal properties. It has shown potential in treating Alzheimer's disease by dose-dependently decreasing the expression of amyloid precursor protein and amyloid-β peptide in human neuroblastoma cells. This suggests that piperlonguminine may help in managing the cognitive decline associated with Alzheimer's.
Used in Antifungal Applications:
Piperlonguminine is employed as an antifungal agent, effective against various fungal pathogens. Its incorporation into pharmaceutical formulations can help combat fungal infections and contribute to improved patient outcomes.
Used in Anticancer Applications:
Piperlonguminine is used as an anticancer agent, demonstrating potential in targeting cancer cells and inhibiting their growth. Its application in cancer treatment may provide an alternative or complementary approach to conventional chemotherapy and radiation therapies.
Used in Antihyperlipidemic Applications:
Piperlonguminine is utilized as an antihyperlipidemic agent, helping to regulate lipid levels in the body. This application can be beneficial for individuals with hyperlipidemia or those at risk of developing cardiovascular diseases.
Used in Anti-inflammatory Applications:
Piperlonguminine is used as an anti-inflammatory agent, reducing inflammation and alleviating pain associated with various conditions. Its incorporation into pharmaceutical or topical formulations can provide relief for patients suffering from inflammatory disorders.
in vitro
in a previous study, piperlonguminine was discovered to inhibit melanin production in melanoma b16 cells stimulated with α-msh, 3-isobutyl-1-methylxanthine or protoporphyrin ix, where piperlonguminine showed stronger depigmenting efficacy. however, piperlonguminine could not alter1-oleoyl-2-acetyl-sn-glycerol-induced melanogenesis and could not affect protein kinase c-mediated melanin production. in additioin, piperlonguminine was not able to inhibit the catalytic activity of cell-free tyrosinase from melanoma b16 cells, and such effect was attributed to the inhibitory action of piperlonguminine on α-msh-induced signaling via camp to the camp responsive element binding protein [1].
in vivo
in vivo, rats were subjected to middle cerebral artery occlusion for 1h, followed by reperfusion for 23 h. the results showed that the intraperitoneal injection of piperlonguminine pe at 2.4 mg/kg was able to produce a significant neuroprotective potential in rats with cerebral ischemia. in addition, piperlonguminine could attenuate the neurological deficit scores, brain infarct volume and brain water content, and could inhibit the activation of nf-κb and mapk [2].
References
Chatterjee, Dutta., Tetrahedron Lett., 1797 (1966)
Chatterjee, Dutta., Tetrahedron, 23, 1769 (1967)
Check Digit Verification of cas no
The CAS Registry Mumber 5950-12-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,9,5 and 0 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 5950-12:
(6*5)+(5*9)+(4*5)+(3*0)+(2*1)+(1*2)=99
99 % 10 = 9
So 5950-12-9 is a valid CAS Registry Number.
InChI:InChI=1/C16H19NO3/c1-12(2)10-17-16(18)6-4-3-5-13-7-8-14-15(9-13)20-11-19-14/h3-9,12H,10-11H2,1-2H3,(H,17,18)
5950-12-9Relevant articles and documents
Mild, Metal-Free and Protection-Free Transamidation of N-Acyl-2-piperidones to Amino Acids, Amino Alcohols and Aliphatic Amines and Esterification of N-Acyl-2-piperidones
Subramani, Muthuraman,Rajendran, Saravana Kumar
, p. 3677 - 3686 (2019/06/08)
Amides are indispensable building blocks of biological systems, pharmaceuticals, and materials. We report a highly selective method for the synthesis of amides via transamidation process. Transamidation of N-acyl-2-piperidones with a broad range of amines is demonstrated under exceedingly mild and metal-free reaction condition that relies on the amide bond twist to weaken the amidic resonance. Transamidation proceeds under the neat condition at room temperature, in short reaction times (30–90 min) with good yields. Considerable variation is tolerated with both amine and imide substrates. Of note, amines bearing carboxylic acids (glycine and serine) and hydroxyl groups (dopamine, tyramine, etc.) are well tolerated which are otherwise problematic under the metal-catalyzed protocol. Our current method is applicable for transamidation of both alkyl and aryl-N-acyl-2-piperidones. The practical value of the method is highlighted by the synthesis of four natural product amide alkaloids in high yields under mild reaction conditions. In the absence of nucleophilic amines, N-acyl-2-piperidones undergoes esterification with EtOH at elevated temperature. Single crystal X-ray analysis of an N-acyl-2-piperidone shows amide bond twist, τ = –20.39° and pyramidalization, χN = –11.73°. This weakens the amidic conjugation and might be the factor controlling the reactivity and selectivity of these imides. We envision that the N-acyl-2-piperidone scaffold would be useful in the synthesis of pharmaceuticals and materials.
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.
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.