63368-34-3

Usage

Uses

Used in Organic Synthesis:
(3,4-DiMethoxybenzyl)-triphenylphosphoniuM chloride serves as a valuable reactant in organic synthesis, particularly for nucleophilic substitutions and organometallic reactions. Its presence of methoxy groups on the benzyl ring enhances its reactivity and makes it suitable for creating a range of chemical products.
Used as a Phase-Transfer Catalyst:
In the chemical industry, (3,4-DiMethoxybenzyl)-triphenylphosphoniuM chloride is utilized as a phase-transfer catalyst. It aids in the efficient transfer of reactants between immiscible phases, thus facilitating smoother and more effective reactions, which is crucial for various chemical processes.
Potential Applications in Pharmaceuticals and Materials Science:
Due to its distinctive chemical structure and reactivity, (3,4-DiMethoxybenzyl)-triphenylphosphoniuM chloride may also find applications in the pharmaceutical sector and materials science. Its potential uses could include the development of new drugs or the synthesis of novel materials with specific properties.

Upstream product

• 603-35-0 triphenylphosphine 
• 7306-46-9 4-chloromethyl-1,2-dimethoxy-benzene 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 

Downstream Products

• 122850-01-5 7-(3',4'-dimethoxyphenyl)heptanoic acid 
• 858847-55-9 3,3',4'-trimethoxystilbene-2-carboxylic acid 
• 111623-27-9 (S)-1-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid ethyl ester 
• 23833-61-6 trans-2-<3,4-Dimethoxy-styryl>-naphthalin 
• 23833-61-6 2-[(Z)-2-(3,4-Dimethoxy-phenyl)-vinyl]-naphthalene 
• 18513-98-9 3,4,3',4'-Tetramethoxystilben 
• 221533-94-4 4-(3,4-dimethoxybenzyl)cyclohexanone 
• 1027550-36-2 8-(3,4-dimethoxy-benzyl)-1,4-dioxa-spiro[4.5]decane 
• 85611-40-1 (S)-6,7-dimethoxy-1-(3,4-dimethoxyphenethyl)-N-methyl-1,2,3,4-tetrahydroisoquinoline 
• 111688-67-6 (S)-1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid ethyl ester 
• 51924-86-8 3',4'-Dimethoxy-2-hydroxystilben 
• 1585206-19-4 1-[(3,4-dimethoxybenzyl)oxy]-2-[2-(3,4-dimethoxyphenyl)ethyl]benzene 
• 1466-17-7 3,4-dimethoxystilbene 
• 14207-97-7 4-Hydroxy-3,3',4'-trimethoxy-stilben 

Relevant academic research and scientific papers

In vitro study and structure-activity relationship analysis of stilbenoid derivatives as powerful vasorelaxants: Discovery of new lead compound

The development of vasorelaxant as the antihypertensive drug is important as it produces a rapid and direct relaxation effect on the blood vessel muscles. Resveratrol (RV), as the most widely studied stilbenoid and the lead compound, inducing the excellent vasorelaxation effect through the multiple signalling pathways. In this study, the in vitro vascular response of the synthesized trans-stilbenoid derivatives, SB 1-8e were primarily evaluated by employing the phenylephrine (PE)-precontracted endothelium-intact isolated aortic rings. Herein we report trans-3,4,4′-trihydroxystilbene (SB 8b) exhibited surprisingly more than 2-fold improvement to the maximal relaxation (Rmax) of RV. This article also highlights the characterization of the aromatic protons in terms of their unique splitting patterns in 1H NMR.

Design, synthesis and antitumour and anti-angiogenesis evaluation of 22 moscatilin derivatives

Two series of moscatilin derivatives were designed, synthesized and evaluated as anti-tumor and anti-angiogenesis agents. Most of these compounds showed moderate-to-obvious cytotoxicity against five cancer cell lines (A549, HepG2, MDA-MB-231, MKN-45, HCT116). Among these cell lines, compounds had obvious effects on HCT116. Especially for 8Ae, the IC50 was low to 0.25 μM. 8Ae can inhibit the viability and induce the apoptosis of HCT116 cells but exhibit no cytotoxic activity in noncancerous NCM460 colon cells. 8Ae can also arrest the G2/M cell cycle in HCT116 cells by inhibiting the α-tubulin expression. Zebrafish bioassay-guided screen showed the 22 moscatilin derivatives had potent anti-angiogenic activities and compound 8Ae had better activities than positive compound. Molecular docking indicated 8Ae interacted with tubulin at the affinity of ?7.2 Kcal/mol. In conclusion, compound 8Ae was a potential antitumor and anti-angiogenesis candidate for further development.

Discovery of an Orally Bioavailable Benzofuran Analogue That Serves as a β-Amyloid Aggregation Inhibitor for the Potential Treatment of Alzheimer's Disease

We developed an orally active and blood-brain-barrier-permeable benzofuran analogue (8, MDR-1339) with potent antiaggregation activity. Compound 8 restored cellular viability from Aβ-induced cytotoxicity but also improved the learning and memory function of AD model mice by reducing the Aβ aggregates in the brains. Given the high bioavailability and brain permeability demonstrated in our pharmacokinetic studies, 8 will provide a novel scaffold for an Aβ-aggregation inhibitor that may offer an alternative treatment for AD.

SAR study on arylmethyloxyphenyl scaffold: Looking for a P-gp nanomolar affinity

Starting from the previously developed P-gp ligands 1a and 1b (EC 50 = 0.25 μM and 0.65 μM, respectively), new arylmethyloxyphenyl derivatives have been synthesized as P-gp modulators in order to investigate: (i) the effect of small electron-do

Synthesis, antiproliferative activity and tubulin targeting effect of acridinone and dioxophenothiazine derivatives

The synthesis of new acridinone and dioxophenothiazine derivatives along with their tubulin polymerization inhibitory and antiproliferative activities is reported. The analysis of correlation for cytotoxic and antitubulin potential of tested compounds sho

Synthesis and antiparasitic and antitumor activity of 2,4-diamino-6- (arylmethyl)-5,6,7,8-tetrahydroquinazoline analogues of piritrexim

Nineteen previously undescribed 2,4-diamino-6-(arylmethyl)-5,6,7,8- tetrahydroquinazolines (5a-m, 10-12) were synthesized as part of a larger effort to assess the therapeutic potential of lipophilic dihydrofolate reductase (DHFR) inhibitors against opportunistic infections of AIDS. Condensation of appropriately substituted (arylmethyl)triphenylphosphoranes with 4,4-ethylenedioxycyclohexanone, followed by hydrogenation (H2/Pd-C) and acidolysis, yielded the corresponding 4-(arylmethyl)cyclohexanones, which were then condensed with cyanoguanidine to form the tetrahydroquinazolines. Three simple 2,4-diamino-6-alkyl-5,6,7,8-tetrahydroquinazoline model compounds (9a-c) were also prepared in one step from commercially available 4-alkylcyclohexanones by this method. Enzyme inhibition assays against rat liver DHFR, Pneumocystis carinii DHFR, and the bifunctional DHFR-TS enzyme from Toxoplasma gondii were carried out, and the selectivity ratios IC50(rat)/IC50(P. carinii) and IC50(rat)/IC50(T. gondii) were compared. The three most potent inhibitors of P. carinii DHFR were the 2,5- dimethoxybenzyl (5j), 3,4-dimethoxybenzyl (5k), and 3,4,5-trimethoxybenzyl (51) analogues, with IC50 values of 0.057, 0.10, and 0.091 μM, respectively. The remaining compounds generally had IC50 values in the 0.1- 1.0 μM range. However all the compounds were more potent against the rat liver enzyme than the P. carinii enzyme and thus were nonselective. The T. gondii enzyme was always more sensitive than the P. carinii enzyme, with most of the analogues giving IC50 values of 0.01-0.1 μM. Moderate 5-10-fold selectivity for T. gondii versus rat liver DHFR was observed with five compounds, the best combination of potency and selectivity being achieved with the 2-methoxybenzyl analogue 5d, which had an IC50 of 0.014 μM and a selectivity ratio of 8.6. One compound (51) was tested for antiproliferative activity against P. carinii trophozoites in culture at a concentration of 10 μg/mL and was found to completely suppress growth over 7 days. The suppressive effect of 51 was the same as that of trimethoprim (10 μg/mL) + sulfamethoxazole (250 μg/mL), a standard clinical combination for the treatment of P. carinii pneumonia in AIDS patients. Four compounds (5a,h,k,l) were tested against T. gondii tachyzoites in culture and were found to have a potency (IC50 = 0.1-0.5 μM) similar to that of pyrimethamine (IC50 = 0.69 μM), a standard clinical agent for the treatment of cerebral toxoplasmosis in AIDS patients. Compound 5h was also active against T. gondii infection in mice when given qdx8 by peritoneal injection at doses ranging from 62.5 (initial dose) to 25 mg/kg. Survival was prolonged to the same degree as with 25 mg/kg clindamycin, another widely used drug against toxoplasmosis. Three compounds (5j-l) were tested for antiproliferative activity against human tumor cells in culture. Among the 25 cell lines in the National Cancer Institute panel for which data were confirmed in two independent experiments, the IC50 for at least two of these compounds was 50 of 50 was 0.01 μM.

Catalytic Oxidation of Reduced Nicotinamide Adenine Dinucleotide by Graphite Electrodes Modified with Adsorbed Aromatics Containing Catechol Functionalities

4-catechol (NSCH2) and 4-catechol (ASCH2) were adsorbed on graphite electrodes.The naphthalene and the ethaneanthracene ring systems were used as anchors to the graphite.The catechol group is free to move out into the electrolyte solution.The electron transfer between the 1,2-hydroquinone functionality and the graphite was fast.The surface coverage was at most 9 x 10-9 mol cm -2.The coenzyme reduced nicotinamide adenine dinucleotide (NADH) could be catalytically oxidized by the immobilized mediating groups.The overvoltage of the NADH oxiadation decreased from 410 mv vs.SCE at the unmodified graphite electrode to 185 mV at the NSCH2 covered electrode at pH 7.=.The reaction rate of the ASCH2 covered electrode was lower than that of the NSCH2 electrode.After 30 min of continuous electrochemical cycling of pH 7.0, 30percent of the original coverage remained for the NSCH2 electrode.