147429-43-4

Basic information

• Product Name: 1,3-Pentadiene, 1-(3,4-methylenedioxybenzyl)-5-(piperidine-1-yl)-
• Synonyms: 1,3-Pentadiene, 1-(3,4-methylenedioxybenzyl)-5-(piperidine-1-yl)-
• CAS NO: 147429-43-4
• Molecular Formula: C17H21 N O2
• Molecular Weight: 271.35
• Mol File: 147429-43-4.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Pentadiene, 1-(3,4-methylenedioxybenzyl)-5-(piperidine-1-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Pentadiene, 1-(3,4-methylenedioxybenzyl)-5-(piperidine-1-yl)-(147429-43-4)
• EPA Substance Registry System: 1,3-Pentadiene, 1-(3,4-methylenedioxybenzyl)-5-(piperidine-1-yl)-(147429-43-4)

Safety Data

• Hazardous Substances Data: 147429-43-4(Hazardous Substances Data)

Usage

Chemical structure

The compound consists of a pentadiene backbone with a 3,4-methylenedioxybenzyl substituent at the 1 position and a piperidine-1-yl substituent at the 5 position.

Potential applications

It has potential applications in pharmaceutical research due to its structural features and potential pharmacological properties.

Biological activity

The compound may possess biological activity and could be of interest for further study in the development of new drugs or biologically active compounds.

Organic synthesis

It may have uses in organic synthesis or as a building block for the preparation of other chemical compounds.

Structural features

The presence of a pentadiene backbone, a 3,4-methylenedioxybenzyl substituent, and a piperidine-1-yl substituent contribute to its potential pharmacological properties and applications.

Further research

The compound may warrant further investigation for its potential use in the development of new drugs or biologically active compounds, as well as its utility in organic synthesis.

Upstream product

• 4711-72-2 piperic acid chloride 
• 110-89-4 piperidine 
• 94-62-2 Piperine 

Relevant articles and documents

Efficient modulation of γ-aminobutyric acid type a receptors by piperine derivatives

Piperine activates TRPV1 (transient receptor potential vanilloid type 1 receptor) receptors and modulates γ-aminobutyric acid type A receptors (GABAAR). We have synthesized a library of 76 piperine analogues and analyzed their effects on GABAAR by means of a two-microelectrode voltage-clamp technique. GABAAR were expressed in Xenopus laevis oocytes. Structure-activity relationships (SARs) were established to identify structural elements essential for efficiency and potency. Efficiency of piperine derivatives was significantly increased by exchanging the piperidine moiety with either N,N-dipropyl, N,N-diisopropyl, N,N-dibutyl, p-methylpiperidine, or N,N-bis(trifluoroethyl) groups. Potency was enhanced by replacing the piperidine moiety by N,N-dibutyl, N,N-diisobutyl, or N,N-bistrifluoroethyl groups. Linker modifications did not substantially enhance the effect on GABAAR. Compound 23 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dipropyl-2,4-pentadienamide] induced the strongest modulation of GABAA (maximal GABA-induced chloride current modulation (IGABA-max = 1673% ± 146%, EC 50 = 51.7 ± 9.5 μM), while 25 [(2E,4E)-5-(1,3-benzodioxol- 5-yl)-N,N-dibutyl-2,4-pentadienamide] displayed the highest potency (EC 50 = 13.8 ± 1.8 μM, IGABA-max = 760% ± 47%). Compound 23 induced significantly stronger anxiolysis in mice than piperine and thus may serve as a starting point for developing novel GABA AR modulators.

NOVEL PIPERINE DERIVATIVES AS GABA-A RECEPTORS MODULATORS

The present invention encompasses novel piperin compounds of general formula (I) wherein R1, R2, R3, m and n are defined as in claim 1, which are suitable for the prevention and/or treatment of diseases mediated by modulation of GABAA receptor and the use thereof for preparing a medicament having the above mentioned properties.

Effects of piperine analogues on stimulation of melanocyte proliferation and melanocyte differentiation

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.