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Upstream product

• 110-89-4 piperidine 
• 110-44-1 hexa-2,4-dienoic acid 
• 618-42-8 1-piperidin-1-yl-ethanone 
• 1796-25-4 1-(2-bromoacetyl)piperidine 
• 110-44-1 sorbic Acid 
• 71627-25-3 1-acetylpiperidine diethyl acetal 
• 2614-88-2 sorbinyl chloride 
• 88855-26-9 1-(1-oxo-3,4-hexadienyl)-piperidin 
• 123-73-9 trans-Crotonaldehyde 
• 112601-97-5 (N-piperidinylcarbonylmethyl)triphenylarsonium bromide 
• 90554-82-8 hexa-2,4-dienoyl chloride 

Relevant academic research and scientific papers

Quorum sensing and nf-κb inhibition of synthetic coumaperine derivatives from piper nigrum

Bacterial communication, termed Quorum Sensing (QS), is a promising target for virulence attenuation and the treatment of bacterial infections. Infections cause inflammation, a process regulated by a number of cellular factors, including the transcription Nuclear Factor kappa B (NF-κB); this factor is found to be upregulated in many inflammatory diseases, including those induced by bacterial infection. In this study, we tested 32 synthetic derivatives of coumaperine (CP), a known natural compound found in pepper (Piper nigrum), for Quorum Sensing Inhibition (QSI) and NF-κB inhibitory activities. Of the compounds tested, seven were found to have high QSI activity, three inhibited bacterial growth and five inhibited NF-κB. In addition, some of the CP compounds were active in more than one test. For example, compounds CP-286, CP-215 and CP-158 were not cytotoxic, inhibited NF-κB activation and QS but did not show antibacterial activity. CP-154 inhibited QS, decreased NF-κB activation and inhibited bacterial growth. Our results indicate that these synthetic molecules may provide a basis for further development of novel therapeutic agents against bacterial infections.

Palladium-catalysed regio- And stereoselective arylative substitution of γ,δ-epoxy-α,β-unsaturated esters and amides by sodium tetraaryl borates

Palladium-catalysed reactions of γ,δ-epoxy-α,β-unsaturated esters and amides with NaBAr4 reagents proceeded regio- and stereoselectively, producing allylic homoallyl alcohols with aryl-substituents in the allylic position for a wide range of substrates. A

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.

Synthesis of coumaperine derivatives: Their NF-κB inhibitory effect, inhibition of cell migration and their cytotoxic activity

Coumaperine (an amide alkaloid, present in white piper) and its derivatives were synthesized and investigated for their cytotoxicity against L428 and A549 cells and their NF-κB inhibitory activity. It was found that the coumaperine derivatives CP-9 and CP-38 suppress NF-κB subunits p50 and p65 in nuclear fractions by western blot and by NF-κB luciferase reporter gene assay in a dose dependent manner. Confirmation of these results was obtained by confocal microscopy. CP-9, CP-32 and CP-38 also exhibited dose dependent cell cytotoxicity in a L428?cells expressing constitutively active NF-κB and in A549?cells, with an IC50 value of 43.25?μg/ml, 0.39?μg/ml and 16.85?μg/ml respectively against L428?cells and 57.15?μg/ml, 69.1?μg/ml and 63.2?μg/ml respectively against A549?cells. In addition, the coumaperine derivatives show remarkable inhibitory activity on the cancer cell migration assay against A549 lung adenocarcinoma cells at the concentrations of 5?μg/ml, 10?μg/ml, and 5?μg/ml of CP-9, CP-32 and CP-38 respectively. Aromatic substituents and number of olefinic double bond in coumaperine derivatives found to influence the inhibitory activity. In luciferase reporter gene assay, di-olefin conjugated coumaperine derivatives, CP-38, CP-32 and PIP exhibited higher inhibitory activity than their corresponding tri-olefin conjugated coumaperine derivatives, CP-102, CP-146 and PIP-155 respectively. CP-32 with a stronger electron donating group (-N(CH3)2) showed better inhibitory activity in luciferase reporter gene assay and in cell proliferation of L428?cells. Simple coumaperine derivative (CP-9, with no substituent) effectively inhibited A549?cells proliferation and migration than the other coumaperine derivatives. CP-9 and CP-38 diminish significantly the NF-κB subunits (p50 and p65) of L428?cells in nuclear fractions at the dosage of 10?μg/ml and 30?μg/ml respectively. Which clearly shows that CP-9 and CP-38 inactivate the NF-κB pathway in?vitro.

Regio- and stereocontrol in the michael-initiated ring-closure reactions of γ,δ-epoxy-α,β-unsaturated esters, ketones, sulfones, and amides

Organozincates or Grignard reagents in the presence of zinc catalysts undergo Michael initiated ring closure (MIRC) reactions with γ,δ-epoxy-α,β-enoates, enones, enesulfones, and enamides to afford 1,2,3-trisubstituted cyclopropanes. The direction of dias

Quantitative structure-activity relationship studies for prediction of antimicrobial activity of synthesized 2,4-hexadienoic acid derivatives

A new series of 2,4-hexadienoic acid derivatives (S1-S42) has been synthesized and evaluated as antimicrobial agents against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Candida albicans, and Aspergillus niger. Quantitative structure-activity relationship (QSAR) investigation using Hansch analysis was applied to find out correlation between antimicrobial activities with physicochemical properties of the synthesized compounds. Various physicochemical descriptors and experimentally determined minimum inhibitory concentration values for different microorganisms were used as independent and dependent variables, respectively. The QSAR revealed that topological parameters especially molecular connectivity indices (χ2, 0χv, 2χv) were found to have overall significant correlation with antimicrobial activity of 2,4-hexadienoic acid derivatives. The statistical results of training set, cross-validated r2 and conventional r values gave reliability to the prediction of molecules with activity using QSAR models.

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.

Syntheses and QSAR studies of sorbic, cinnamic and ricinoleic acid derivatives as potential antibacterial agents

Amides and esters of sorbic, cinnamic and ricinoleic acid have been synthesized and evaluated for their antibacterial activity against gram (+) ve S. aureus, B. subtilis and gram (-) ve E. coli. Most of the compounds have shown moderate to good activity against microorganisms under test. Linear regression analysis of descriptors related to lipophilicity, steric and electronic parameters against antibacterial activity have been performed. QSAR studies indicated the predominance of electronic and steric parameters over the lipophilicity parameters in contributing antibacterial activity.

A FACILE AND HIGHLY STEREOSELECTIVE SYNTHESIS OF (2E)-, (2E,4E)-UNSATURATED AMIDES AND RELATED NATURAL PRODUCTS

A facile synthesis of (2E)- and (2E, 4E)-unsaturated amides was achieved via arsonium bromides with high stereoselectivity.Its application to the synthesis of related natural products 4 and 5 is also reported.

A Facile Synthesis of 3,4-Dienamides by the Reaction of Propargyl Alcohols with Cyclic Amide Acetals and Their Stereoselective Rearrangement to 2(E),4(Z)-Dienamides Promoted with Alumina. Total Synthesis of Isochavicine

Thermal condensation of propargyl alcohols with acetals of 1-acetylpyrrolidine and 1-acetylpiperidine gave 3,4-dienamides in good yields.Alumina promoted the rearrangement of β-allenic amides to 2(E),4(Z)-dienamides stereoselectively.Its application to the synthesis of isochavicine of pepper components is described.Carbon-13 NMR data of these dienamides were obtained.