6713-26-4

Usage

Chemical class

Piperazine class of compounds

Type of compound

Diium salt

Positively charged nitrogen atoms

Two

Potential use

Pharmaceutical ingredient

Studied for

Treatment of various medical conditions

Structural features

Presence of ethoxy and methoxy groups

Structural features

Presence of pyridin-2-ylmethyl group

Lipophilicity

Suggests some degree of lipophilicity due to ethoxy and methoxy groups

Interaction with lipid membranes

Potential interaction due to lipophilicity

Biological interactions

Potential interactions with biological systems containing pyridine-based molecules

Research status

Further research needed to fully elucidate chemical and biological properties
This list provides a summary of the key properties and specific content of 1-(3-ethoxy-4-methoxybenzyl)-4-(pyridin-2-ylmethyl)piperazinediium based on the information provided.

Upstream product

• 508-02-1 Oleanolic acid 

Downstream Products

• 4748-12-3 28-nor-olean-17-en-3β-ol 
• 51361-60-5 olean-13(18)-en-3β-yl acetate 

Relevant academic research and scientific papers

Synthesis and anti-inflammatory activity of saponin derivatives of δ-oleanolic acid

Pentacyclic triterpenes (PTs) are the active ingredients of many medicinal herbs and pharmaceutical formulations, and are well-known for their anti-inflammatory activity. On the other hand, anti-inflammatory effects of AMP-activated protein kinase (AMPK) have recently drawn much attention. In this study, we found that a variety of naturally occurring PTs sapogenins and saponins could stimulate the phosphorylation of AMPK, and identified δ-oleanolic acid (10) as a potent AMPK activator. Based on these findings, 23 saponin derivatives of δ-oleanolic acid were synthesized in order to find more potent anti-inflammatory agents with improved pharmacokinetic properties. The results of cellular assays showed that saponin 29 significantly inhibited LPS-induced secretion of pro-inflammatory factors TNF-α and IL-6 in THP1-derived macrophages. Preliminary mechanistic studies showed that 29 stimulated the phosphorylation of AMPK and acetyl-CoA carboxylase (ACC). The bioavailability of 29 was significantly improved in comparison with its aglycon. More importantly, 29 showed significant anti-inflammatory and liver-protective effects in LPS/D-GalN-induced fulminant hepatic failure mice. Taken together, PTs saponins hold promise as therapeutic agents for inflammatory diseases.

Protonated montmorillonite-mediated highly specific isomerization of oleanolic acid esters: Application to the synthesis of Δ13(18)-CDDO-Me

A one-pot highly specific isomerization of oleanolic acid esters (5a-g) to δ-oleanolic acid esters (6a-g) was achieved in the presence of proton-exchanged montmorillonite (H-mont) under mild reaction conditions. This protocol could proceed smoothly on a 15.0 gram scale. Based on this methodology, the synthesis of the biologically active compound Δ13(18)-CDDO-Me (4) was realized.