78765-31-8

Upstream product

• 3970-21-6 2-Methoxyethoxymethyl chloride 
• 121-33-5 vanillin 

Downstream Products

• 875153-09-6 [3-methoxy-4-(2-methoxy-ethoxymethoxy)-phenyl]-methanol 
• 491-71-4 chrysoeriol 
• 1456788-20-7 3'-methoxy-4',5,7-tri[(2-methoxyethoxy)methoxy]flavone 
• 1456788-26-3 5-hydroxy-3'-methoxy-4',7-di[(2-methoxyethoxy)methoxy]flavone 
• 1456788-16-1 2'-hydroxy-3-methoxy-4,4',6'-tri[(2-methoxyethoxy)methoxy]chalcone 
• 78765-32-9 3-methoxy-4-<2'-(methoxyethoxy)methoxy>-propiophenone 
• 78765-33-0 3,4-bis-(3'-methoxy-4'-hydroxyphenyl)-3-hexene 
• 124956-21-4 (2E,4E)-5-[3-Methoxy-4-(2-methoxy-ethoxymethoxy)-phenyl]-penta-2,4-dienoic acid {4-[4-(1H-indol-3-yl)-piperidin-1-yl]-butyl}-amide 
• 124956-20-3 (2E,4E)-5-[3-Methoxy-4-(2-methoxy-ethoxymethoxy)-phenyl]-penta-2,4-dienoic acid {3-[4-(1H-indol-3-yl)-piperidin-1-yl]-propyl}-amide 
• 124956-19-0 (2E,4E)-5-[3-Methoxy-4-(2-methoxy-ethoxymethoxy)-phenyl]-penta-2,4-dienoic acid {2-[4-(1H-indol-3-yl)-piperidin-1-yl]-ethyl}-amide 
• 124956-25-8 (2E,4E)-5-(4-Hydroxy-3-methoxy-phenyl)-penta-2,4-dienoic acid {2-[4-(1H-indol-3-yl)-piperidin-1-yl]-ethyl}-amide 
• 101619-46-9 (2E,4E)-5-(3-methoxy-4-((2-methoxyethoxy)methoxy)phenyl)-penta-2,4-dienoic acid 
• 859172-13-7 acetic acid 2-chloro-5-methoxy-4-(2-methoxy-ethoxymethoxy)-benzyl ester 

Relevant academic research and scientific papers

Exploring cinnamic acid scaffold: development of promising neuroprotective lipophilic antioxidants

New lipophilic hydroxycinnamic acid based derivatives were designed and synthesized and their antioxidant and neuroprotective activities evaluated. The chemical modification introduced in the cinnamic acid scaffold leads to compounds with amplified lipophilicity and in general with increased antioxidant activity when compared to natural models (caffeic and ferulic acids). The compounds did not display cytotoxicity and present a significant neuroprotective effect against 6-OH-DA induced damage to SH-SY5Y cells. Compound 6 stands out as an efficient radical scavenger and iron(ii) chelator that ensures drug-like properties. Moreover, neuroprotection against oxidative damage was observed even at low concentration (1 μM). Therefore, compound 6 developed by a biology-oriented approach displays a combination of important features for a further optimization process that will generate a new effective antioxidant with therapeutic application for oxidative-stress-related events, namely neurodegenerative diseases.

Modulation of human neutrophils' oxidative burst by flavonoids

Inflammation is a normal response towards tissue injury, but may become deleterious to the organism if uncontrolled. The overproduction of reactive species during the inflammatory process may cause or magnify the damage at inflammatory sites. Flavonoids have been suggested as therapeutic agents to avoid such damage, as these compounds exhibit anti-inflammatory activity, through the modulation of oxidative stress and signalling pathways. Both effects may attenuate neutrophils' activities at inflammatory sites. In this study,we investigated the structure/activity relationship of a series of flavonoids on the oxidative burst of human neutrophils in vitro, as a measure of its anti-inflammatory potential. Neutrophils were stimulated with phorbol-12-myristate-13-acetate, and fluorescence and chemiluminescence techniques were used to evaluate the generation of reactive oxygen species. All the tested flavonoids revealed the ability to modulate the neutrophil 's oxidative burst. From the obtained results, the pivotal role of the catechol group in the B-ringwas evidenced as well as the minor importance of the hydroxylations in the A-ring, which did not appear to be determinant for the activity, although clearly influencing the lipophilicity of the tested flavonoids. It is also clarified the importance of the methylation in the OH group at the B-ring catechol moiety. In conclusion, the obtained results uncover new possible strategies for the resolution of inflammatory processes, using flavonoids to modulate neutrophil's oxidative burst.

The taming of capsaicin. Reversal of the vanilloid activity of N-acylvanillamines by aromatic iodination

Aromatic iodination ortho to the phenolic hydroxyl reverts the activity of the ultrapotent vanilloid agonist resiniferatoxin (RTX, 1a), generating the ultrapotent antagonist 5′-iodoRTX (1b). To better understand the role of iodine in this remarkable switch of activity, a systematic investigation on the halogenation of vanillamides, a class of compounds structurally simpler than resiniferonoids, was carried out. The results showed that (a) the antagonistic activity depends on the site of halogenation and is maximal at C-6′, (b) iodine is more efficient than chlorine and bromine at reverting the agonistic activity, and (c) iodine-carbon exchange decreases antagonist activity. Iodine-induced reversal of vanilloid activity was also observed in vanillamides more powerful than capsaicin, but a poor correlation was found between agonistic and antagonistic potencies, suggesting that differences exist in the way vanillamides and their 6′-iodo derivatives bind to TRPV1.″

3-PHENYL-N- ((1, 3, 4) THIADIAZOL-2-YL) -ACRYLAMIDE DERIVATIVES AND RELATED COMPOUNDS AS MODULATORS OF ESTROGEN-RELATED RECEPTORS FOR THE TREATMENT OF E.G. CANCER, RHEUMATOID ARTHRITIS OR NEUROLOGICAL DISORDERS

Compounds of formula (I) are provided as well as compositions and methods of using compounds of formula (I) for modulating the activity of the estrogen-related receptors and for the treatment, prevention, or amelioration of one or more symptoms of disease or disorder related to the activity of the estrogen-related receptor. Considering the wide range of activity of the nuclear hormone receptor ERRα, the compounds described herein which are capable of modulating ERRα activity, are useful for treating a range of disease states including cancer, diabetes, obesity, hyperlipidermia, arthritis, atherosclerosis, osteoporosis, anxiety, depression, Parkinson’s disease and Alzheimer’s disease. Formula (I). The substituents are defined in the claims.

(2E,4E)-N-(4-(1H-indol-3-yl)piperidin-1-yl)alkyl-5-(substituted phenyl)-2,4-pentadienamides as antiallergic agents with antihistaminic and anti slow-reacting substance (SRS) activities

As an extension of our study aiming to discover a novel compound with dual activities against histamine and slow-reacting substance (SRS), we synthesized two types of indolylpiperidine derivatives, 3 and 4-20. Testing for in vivo antianaphylactic activity and for in vitro anti-SRS activity revealed that (2E,4E)-5-(3,5-dimethoxy-4-hydroxyphenyl)-N-(2-(4-(1H-indol-3-yl)piper idin-1-yl)ethyl)-2,4-pentadienamide (11) exhibited potent dual activities with ED50 = 0.89 mg/kg and IC50 = 1.43 μM, respectively. However, the plasma concentration of unchanged 11 was very low when administered orally in guinea pigs. This result can be explained by fast formation of a glucuronic acid conjugate.

SYNTHESIS OF METABOLIC INTERMEDIATES OF DIETHYLSTILBESTROL

This report details the synthesis of 1) 3,4,4'-trihydroxy-α,α'-diethyl-trans-stilbene; 2) 3,4-bis-(p-hydroxyphenyl)-trans-3-hexenol; 3) 3,4-bis-(p-hydroxyphenyl)-2,4-cis,cis-hexadienol; 4) 3,4-bis-(3'-methoxy-4'-hydroxyphenyl)-trans-3-hexene; 5) 3,4-bis-(3',4'-dimethoxyphenyl)-trans-3-hexene.These compounds are suspected metabolites of diethylstilbestrol.