78055-65-9

Usage

InChI:InChI=1/C13H21O5P/c1-5-17-19(14,18-6-2)10-11-7-8-12(15-3)13(9-11)16-4/h7-9H,5-6,10H2,1-4H3

Upstream product

• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 122-52-1 triethyl phosphite 
• 7306-46-9 4-chloromethyl-1,2-dimethoxy-benzene 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 78-40-0 triethyl phosphate 
• 2150-38-1 methyl 3,4-dimethoxybenzoate 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 76950-82-8 1-(3,4-Dimethoxy-benzyl)-2-methylsulfanyl-4,6-diphenyl-pyridinium; iodide 

Downstream Products

• 83088-26-0 (E)-tetramethylpiceatannol 
• 18513-98-9 3,4,3',4'-Tetramethoxystilben 
• 3892-92-0 (E)-3,4-dimethoxystilbene 
• 186446-30-0 3,4,2',4',5'-pentamethoxy-trans-stilbene 
• 18259-12-6 3,4,2′,4′,6′-pentamethoxy-trans-stilbene 
• 1219801-02-1 4-(3,4-dimethoxyphenethyl)benzene-1,2,3-triol 

Relevant academic research and scientific papers

Synthetic method for dihydrostilbenes and anti-inflammatory compounds containing thereof

The present invention aims to provide an effective anti-inflammatory agent without side effects. The present inventors have invented a method for efficiently synthesizing dihydrostilbene and derivatives (compounds 1 to 5) from starting materials at a high yield. In addition, the anti-inflammatory effects were evaluated in LPS-induced RAW-264.7 macrophages. The compounds of dihydrostilbene do not exhibit cytotoxicity and are shown to weakly or well inhibit nitric oxide production induced by LPS at the concentration of 10 andmu;M.COPYRIGHT KIPO 2018

Discovery of boron-containing compounds as Aβ aggregation inhibitors and antioxidants for the treatment of Alzheimer's disease

A novel series of boron-containing compounds were designed, synthesized and evaluated as multi-target-directed ligands against Alzheimer's disease. The biological activity results demonstrated that these compounds possessed a significant ability to inhibit self-induced Aβ aggregation (20.5-82.8%, 20 μM) and to act as potential antioxidants (oxygen radical absorbance capacity assay using fluorescein (ORAC-FL) values of 2.70-5.87). In particular, compound 17h is a potential lead compound for AD therapy (IC50 = 3.41 μM for self-induced Aβ aggregation; ORAC-FL value = 4.55). Compound 17h also functions as a metal chelator. These results indicated that boron-containing compounds could be new structural scaffolds for the treatment of AD.

Synthesis, biological evaluation and docking studies of trans-stilbene methylthio derivatives as cytochromes P450 family 1 inhibitors

Cytochromes P450 family 1 (CYP1) are responsible for the metabolism of procarcinogens, for example polycyclic aromatic hydrocarbons and aromatic and heterocyclic amines. The inhibition of CYP1 activity is examined in terms of chemoprevention and cancer chemotherapy. We designed and synthesized a series of trans-stilbene derivatives possessing a combination of methoxy and methylthio functional groups attached in different positions to the trans-stilbene skeleton. We determined the effects of synthesized compounds on the activities of human recombinant CYP1A1, CYP1A2 and CYP1B1 and, to explain the variation of inhibitory potency of methoxystilbene derivatives and their methylthio analogues, we employed computational analysis. The compounds were docked to CYP1A1, CYP1A2 and CYP1B1 binding sites with the use of Accelrys Discovery Studio 4.0 by the CDOCKER procedure. For CYP1A2 and CYP1B1, values of scoring functions correlated well with inhibitory potency of stilbene derivatives. All compounds were relatively poor inhibitors of CYP1A2 that possess the most narrow and flat enzyme cavity among CYP1s. For the most active CYP1A1 inhibitor, 2-methoxy-4′-methylthio-trans-stilbene, a high number of molecular interactions was observed, although the interaction energies were not distinctive.

Dihydrostilbenes and diarylpropanes: Synthesis and in vitro pharmacological evaluation as potent nitric oxide production inhibition agents

An efficient synthesis of dihydrostilbenes (1–5) and diarylpropanes (6–10) is achieved from the commercially available starting materials and Wittig-Horner reaction, Claisen–Schmidt condensation and hydrogenation as key steps. Later, their nitric oxide (NO) production inhibition effects were evaluated in lipopolysaccharide (LPS)-induced RAW-264.7 macrophages as an indicator of anti-inflammatory activity. All the tested compounds significantly decreased NO production in a concentration-dependent manner except compounds 2, 6 and 8 and did not show notable cytotoxicity except compound 1. Two compounds i.e., compound 9 (hindsiipropane B) (100%; IC50?=?1.84?μM) possessed the most potent NO inhibitory activity which was even stronger than the positive control, L-NMMA (90.1%; IC50?=?2.73?μM) followed by compound 4 (75.5%; IC50?=?2.98?μM) at 10?μM concentration and this finding was also further correlated by suppressed expression of LPS stimulated inducible NO synthase. Our study revealed that compound 9, a 1,3-diarylpropane scaffold with 3″,4″-dimethoxyphenyl and 3′,4′-dihydroxy-2′-methoxyphenyl motifs could be considered as potential compound or lead compound for further development of NO production-targeted anti-inflammatory agents.

3,4,2′-Trimethoxy-trans-stilbene-a potent CYP1B1 inhibitor

A novel series of methoxy-trans-stilbenes with 3,4-dimethoxy motifs was designed and synthesized. The inhibitory potency of 3,4-dimethoxystilbene derivatives against cytochrome P450 isozymes CYP1A1, CYP1B1 and CYP1A2 was evaluated. 3,4,2′-Trimethoxy-trans-stilbene (3,4,2′-TMS) exhibited extremely potent inhibitory action against CYP1B1 activity with an IC 50 of 0.004 μM. 3,4,2′-TMS exhibited 90-fold selectivity for CYP1B1 over CYP1A1 and 830-fold selectivity for CYP1B1 over CYP1A2. However, 3,4,2′,4′-tetramethoxy-trans-stilbene appeared to be the most selective inhibitor of both CYP1B1 and CYP1A1 showing very low affinity toward CYP1A2. Complementary experimental studies and computational methods were used to explain what structural determinants decide the specific affinity of stilbene derivatives to CYP1A2 and CYP1B1 binding sites.

Euodenine A: A small-molecule agonist of human TLR4

A small-molecule natural product, euodenine A (1), was identified as an agonist of the human TLR4 receptor. Euodenine A was isolated from the leaves of Euodia asteridula (Rutaceae) found in Papua New Guinea and has an unusual U-shaped structure. It was synthesized along with a series of analogues that exhibit potent and selective agonism of the TLR4 receptor. SAR development around the cyclobutane ring resulted in a 10-fold increase in potency. The natural product demonstrated an extracellular site of action, which requires the extracellular domain of TLR4 to stimulate a NF-κB reporter response. 1 is a human-selective agonist that is CD14-independent, and it requires both TLR4 and MD-2 for full efficacy. Testing for immunomodulation in PBMC cells shows the induction of the cytokines IL-8, IL-10, TNF-α, and IL-12p40 as well as suppression of IL-5 from activated PBMCs, indicating that compounds like 1 could modulate the Th2 immune response without causing lung damage.

Synthesis and bioactivity of resveratrol analogues

It has been reported that resveratrol enhanced SIRT1 expression and significantly mimicked calorie restriction by stimulating Sir2 which is the most homologic homologue of SIRT1 of mammalian. A series of novel resveratrol derivatives were designed and synthesized as novel SIRT1 activator candidates. These synthesized compounds were characterized by spectral (1H NMR) analysis and examined for their Sir2 activation against yeast parental strain-BY4743 at a concentration of 100 μM/L by Bioscreen C MBR machine. Several compounds showed a promising Sir2 activation activity compared with resveratrol. Meanwhile, the structure-activity relationships with Sirt2 activation activities were also discussed.

A2A ADENOSINE RECEPTOR ANTAGONISTS

The present invention relates to novel compounds that are A2A adenosine receptor antagonists, and to their use in treating mammals for various disease states, such as CNS disorders, including the "movement disorders" (Parkinson's disease, Huntington's Chorea, and catalepsy), and cerebral ischemia, excitotoxicity, cognitive and physiological disorders, depression, ADHD, hepatic fibrosis, cirrhosis of the liver, and drug addiction (alcohol, amphetamine, cannabinoids, cocaine, nicotine, and opioids) and to their use in the enhancement of immune response. The invention also relates to methods for the preparation of such compounds, and to pharmaceutical compositions containing them.

Chroman/catechol hybrids: Synthesis and evaluation of their activity against oxidative stress induced cellular damage

Three series of chromans substituted at positions 2 or 5 by catechol derivatives were synthesized, and their activity against oxidative stress induced cellular damage was studied. Specifically, the ability of the new molecules to protect cultured cells fr

Synthesis and properties of phosphorylated 4-methylpyrocatechol derivatives

Procedures for preparing α-phosphorylated 4-methylpyrocatechols were developed. Diphenyl-(3,4-dimethoxybenzyl)phosphine oxide yields diphenyl(3,4-dihydroxybenzyl)phosphine oxide under the action of hydrobromic acid. 2005 Pleiades Publishing, Inc.