92356-77-9

Upstream product

• 110-89-4 piperidine 
• 443360-67-6 (2E,4E)-5-(4-Dimethylamino-phenyl)-penta-2,4-dienoyl chloride 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 3626-69-5 N-crotonoylpiperidine 
• 92356-73-5 5t-(4-dimethylamino-phenyl)-penta-2t,4-dienoic acid methyl ester 
• 15542-38-8 (2E,4E)-5-[4-(dimethylamino)phenyl]-2,4-pentadienoic acid 

Relevant academic research and scientific papers

Design, synthesis and identification of novel coumaperine derivatives for inhibition of human 5-LOX: Antioxidant, pseudoperoxidase and docking studies

5-Lipoxygenase (5-LOX) is a key enzyme involved in the biosynthesis of pro-inflammatory leukotrienes, leading to asthma. Developing potent 5-LOX inhibitors especially, natural product based ones, are highly attractive. Coumaperine, a natural product found in white pepper and its derivatives were herein developed as 5-LOX inhibitors. We have synthesized twenty four derivatives, characterized and evaluated their 5-LOX inhibition potential. Coumaperine derivatives substituted with multiple hydroxy and multiple methoxy groups exhibited best 5-LOX inhibition. CP-209, a catechol type dihydroxyl derivative and CP-262-F2, a vicinal trihydroxyl derivative exhibited, 82.7% and 82.5% inhibition of 5-LOX respectively at 20 μM. Their IC50 values are 2.1 ± 0.2 μM and 2.3 ± 0.2 μM respectively, and are comparable to zileuton, IC50 = 1.4 ± 0.2 μM. CP-155, a methylenedioxy derivative (a natural product) and CP-194, a 2,4,6-trimethoxy derivative showed 76.0% and 77.1% inhibition of 5-LOX respectively at 20 μM. Antioxidant study revealed that CP-209 and 262-F2 (at 20 μM) scavenged DPPH radical by 76.8% and 71.3% respectively. On the other hand, CP-155 and 194 showed very poor DPPH radical scavenging activity. Pseudo peroxidase assay confirmed that the mode of action of CP-209 and 262-F2 were by redox process, similar to zileuton, affecting the oxidation state of the metal ion in the enzyme. On the contrary, CP-155 and 194 probably act through some other mechanism which does not involve the disruption of the oxidation state of the metal in the enzyme. Molecular docking of CP-155 and 194 to the active site of 5-LOX and binding energy calculation suggested that they are non-competitive inhibitors. The In-Silico ADME/TOX analysis shows the active compounds (CP-155, 194, 209 and 262-F2) are with good drug likeliness and reduced toxicity compared to existing drug. These studies indicate that there is a great potential for coumaperine derivatives to be developed as anti-inflammatory drug.

Piperine derivative as well as preparation method and application thereof

The invention provides a piperine derivative as well as a preparation method and an application thereof. The piperine derivative is a compound shown as a formula (I), or a salt thereof, or a stereoisomer thereof, or a hydrate thereof. The compound provided by the invention can effectively protect nerve cells and improve the survival rate of the nerve cells, so that the compound provided by the invention can effectively treat neurodegenerative diseases and can be used for preparing medicines for treating the neurodegenerative diseases.

Synthetic and spectroscopic studies of structural analogs of piper amides - The 5-aryl-2E,4E-pentadienamides

The methyl esters and piperidides of fourteen 5-aryl-2E,4E-pentadienoic acids have been synthesized starting from the corresponding aryl aldehydes.

Substituent Effects on Carbon-13 NMR Chemical Shifts of Side-chain Carbons in 5-Aryl-2E,4E-pentadienoic Acid Derivatives

The 13C NMR spectra of two series of 5-aryl-2E,4E-pentadienoic acid derivatives, viz. the methyl esters and piperidides have been determined.The chemical shifts of C-2 and C-4 show very good correlations with the Hammett ?+-constants for all the substituents investigated, except for the para-nitro group which is capable of excerting a strong -R effect.A possible explanation for this has been advanced.Hammett correlations between substituents and the chemical shifts of both C-3 and C-5 carbons using ?0 parameters are less satisfactory.A reverse chemical shift effect has been observed for these two centres.