3929-47-3

Usage

Uses

Used in Pharmaceutical Industry:
3-(3,4-DIMETHOXYPHENYL)-1-PROPANOL is used as an intermediate compound for the synthesis of various pharmaceuticals, specifically in the production of fluorinated benzamide neuroleptic. The expression is: 3-(3,4-DIMETHOXYPHENYL)-1-PROPANOL is used as a synthetic intermediate for the creation of (S)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(3-fluoropropyl)-2,3-dimethoxybenzamide, which is a neuroleptic agent with potential applications in the treatment of various neurological and psychiatric disorders.

InChI:InChI=1/C11H16O3/c1-13-10-6-5-9(4-3-7-12)8-11(10)14-2/h5-6,8,12H,3-4,7H2,1-2H3

Upstream product

• 5462-13-5 ethyl 3-(3,4-dimethoxyphenyl)propionate 
• 2107-70-2 3,4-methoxycinnamic acid 
• 40918-90-9 3'-Hydroxymethyleugenol 
• 27798-73-8 methyl 3-(3,4-dimethoxyphenyl)propionate 
• 61871-67-8 3-(3,4-Dimethoxyphenyl)propanal 
• 6258-35-1 3-(3,4-dimethoxyphenyl)prop-2-yn-1-ol 
• 18523-76-7 (E)-3',4'-dimethoxycinnamyl alcohol 
• 70570-23-9 (Z)-3-(3,4-dimethoxyphenyl)-2-propen-1-ol 
• 75-09-2 dichloromethane 
• 20583-78-2 ethyl (E)-3,4-dimethoxycinnamate 
• 1392108-14-3 O-(3,4-dimethoxyphenylpropyl)-N-benzoyl-N-phenylhydroxylamine 
• 22676-00-2 [1-(3,4-dimethoxyphenyl)-2-(4-methoxyphenoxy)-1,3-dihydroxypropane] 
• 10535-17-8 1-(3,4-dimethoxyphenyl)-2-(methoxyphenoxy)propane-1,3-diol 
• 58045-88-8 3,4-dimethoxycinnamaldehyde 

Downstream Products

• 110406-97-8 4-(4-chloropropyl)-1,2-dimethoxybenzene 
• 13575-74-1 4-(3,4-dimethoxyphenyl)butanoic acid 
• 3916-70-9 1,2-dimethoxy-4-(3-nitropropyl)benzene 
• 13575-75-2 6,7-dimethoxy-1-oxo-1,2,3,4-tetrahydronaphthalene 
• 3945-85-5 1-bromo-3-(3,4-dimethoxyphenyl)propane 
• 314741-29-2 1-[3-(3,4-Dimethoxyphenyl)-propyl]-4-[2-(R,S)-hydroxy-2-(6-methoxyquinolin-4-yl)ethyl]piperazine 
• 1204428-33-0 C₁₆H₂₄O₃ 
• 1204428-32-9 4-(3-(cyclopropylmethoxy)propyl)-1,2-dimethoxybenzene 
• 1392108-14-3 O-(3,4-dimethoxyphenylpropyl)-N-benzoyl-N-phenylhydroxylamine 

Relevant academic research and scientific papers

DOPAMINE RECEPTOR D1 AGONISTS AND METHODS OF USE

Described herein are small molecule agonists of dopamine receptor D1 that inhibit YAP/TAZ, compositions, and methods of using these compounds and compositions.

Synthesis and Studies of Potential Inhibitors of CD73 Based on a Triazole Scaffold

The ecto-5′-nucleotidase CD73 is involved in the production of immunosuppressive adenosine in the tumoral microenvironment and recently became a validated target in immuno-oncology. To avoid formation of CD73-produced adenosine, several series of potential inhibitors of the target enzyme based on a triazole scaffold were synthetized and evaluated on recombinant purified hCD73 and in cell-based assays.

Copper-Catalyzed Intermolecular Enantioselective Radical Oxidative C(sp3)?H/C(sp)?H Cross-Coupling with Rationally Designed Oxazoline-Derived N,N,P(O)-Ligands

The intermolecular asymmetric radical oxidative C(sp3)?C(sp) cross-coupling of C(sp3)?H bonds with readily available terminal alkynes is a promising method to forge chiral C(sp3)?C(sp) bonds because of the high atom and step economy, but remains underexplored. Here, we report a copper-catalyzed asymmetric C(sp3)?C(sp) cross-coupling of (hetero)benzylic and (cyclic)allylic C?H bonds with terminal alkynes that occurs with high to excellent enantioselectivity. Critical to the success is the rational design of chiral oxazoline-derived N,N,P(O)-ligands that not only tolerate the strong oxidative conditions which are requisite for intermolecular hydrogen atom abstraction (HAA) processes but also induce the challenging enantiocontrol. Direct access to a range of synthetically useful chiral benzylic alkynes and 1,4-enynes, high site-selectivity among similar C(sp3)?H bonds, and facile synthesis of enantioenriched medicinally relevant compounds make this approach very attractive.

In silico design and synthesis of N-arylalkanyl 2-naphthamides as a new class of non-purine xanthine oxidase inhibitors

A series of N-arylalkanyl 2-naphthamides (Xa~e), which were predicted from virtual molecular docking on a built xanthine oxidase template as potential inhibitors, were synthesized. Their inhibitory activity against xanthine oxidase was assayed. Among these prepared, compounds Xb (IC50 13.6?μM), Xc (IC50 13.1?μM), and Xd (IC50 12.5?μM) showed comparable inhibitory activity to allopurinol (IC50 22.1?μM). The in vitro assay result correlated well with molecular docking scores, ΔG?=??16.99, ?17.66, and ?17.13 Kcal/mol, respectively. On the potassium oxonate-induced hyperuricemic mice model, oral administration of Xc-Ac (40 mg/ Kg), the per-O-acetylated Xc, could reduce the blood uric acid level by 60% in comparison to the normal control group and is statistically significant (p .01) while compared with the hyperuricemic mice group.

Cleavage of aryl-ether bonds in lignin model compounds using a Co-Zn-beta catalyst

Efficient cleavage of aryl-ether linkages is a key strategy for generating aromatic chemicals and fuels from lignin. Currently, a popular method to depolymerize native/technical lignin employs a combination of Lewis acid and hydrogenation metal. However, a clear mechanistic understanding of the process is lacking. Thus, a more thorough understanding of the mechanism of lignin depolymerization in this system is essential. Herein, we propose a detailed mechanistic study conducted with lignin model compounds (LMC) via a synergistic Co-Zn/Off-Al H-beta catalyst that mirrors the hydrogenolysis process of lignin. The results suggest that the main reaction paths for the phenolic dimers exhibiting α-O-4 and β-O-4 ether linkages are the cleavage of aryl-ether linkages. Particularly, the conversion was readily completed using a Co-Zn/Off-Al H-beta catalyst, but 40% of α-O-4 was converted and β-O-4 did not react in the absence of a catalyst under the same conditions. In addition, it was found that the presence of hydroxyl groups on the side chain, commonly found in native lignin, greatly promotes the cleavage of aryl-ether linkages activated by Zn Lewis acid, which was attributed to the adsorption between Zn and the hydroxyl group. Followed by the cobalt catalyzed hydrogenation reaction, the phenolic dimers are degraded into monomers that maintain aromaticity. This journal is

BIOISPIRED PROTEASOME ACTIVATORS WITH ANTIAGEING ACTIVITY

The present invention relates to novel bio-inspired hybrid compounds of formula I which act as proteasome activators and exhibit anti-ageing activity, as well as methods for their synthesis. These hybrid compounds combine the structural features of hydroxytyrosol and the natural antioxidant vitamin E or its bioisosteres in one molecular scaffold. The compounds of formula I, which include structural proteasome activators (activation by stereochemical interaction), can be used in the production of anti-ageing products, such as cosmetic preparations. Additionally, they can be used in conditions and diseases where the proteasome is down-regulated, as well as proteasome-activation control compounds.

Structural optimization of natural product nordihydroguaretic acid to discover novel analogues as AcrB inhibitors

Drug efflux pumps confer multidrug resistance to dangerous bacterial pathogens which makes these proteins promising drug targets. Herein, we present initial chemical optimization and structure-activity relationship (SAR) data around a previously described efflux pump inhibitor, nordihydroguaretic acid (NDGA). Four series of novel NDGA analogues that target Escherichia coli AcrB were designed, synthesized and evaluated for their ability to potentiate the activity of antibiotics, to inhibit AcrB-mediated substrate efflux and reduce off-target activity. Nine novel structures were identified that increased the efficacy of a panel of antibiotics, inhibited drug efflux and reduced permeabilization of the bacterial outer and inner membranes. Among them, WA7, WB11 and WD6 possessing broad-spectrum antimicrobial sensitization activity were identified as NDGA analogues with favorable properties as potential AcrB inhibitors, demonstrating moderate improvement in potency as compared to NDGA. In particular, WD6 was the most broadly active analogue improving the activity of all four classes of antibacterials tested.

EC18 as a Tool to Understand the Role of HCN4 Channels in Mediating Hyperpolarization-Activated Current in Tissues

Hyperpolarization-activated cyclic nucleotide-gated (HCN) channels are membrane proteins encoded by four genes (HCN1-4) and widely distributed in the central and peripheral nervous system and in the heart. HCN channels are involved in several physiological functions, including the generation of rhythmic activity, and are considered important drug targets if compounds with isoform selectivity are developed. At present, however, few compounds are known, which are able to discriminate among HCN channel isoforms. The inclusion of the three-methylene chain of zatebradine into a cyclohexane ring gave a compound (3a) showing a 5-fold preference for HCN4 channels, and ability to selectively modulate Ih in different tissues. Compound 3a has been tested for its ability to reduce Ih and to interact with other ion channels in the heart and the central nervous system. Its preference for HCN4 channels makes this compound useful to elucidate the contribution of this isoform in the physiological and pathological processes involving hyperpolarization-activated current.

Total Synthesis and Evaluation of B-Homo Palmatine and Berberine Derivatives as p300 Histone Acetyltransferase Inhibitors

Palmatine and berberine, structurally similar isoquinoline alkaloids exhibiting a broad range of biological activities, were recently found to inhibit p300 histone acetyltransferase (HAT), a potential therapeutic target for treating transcriptional activator-driven malignancies and diseases. Here, we report the first total synthesis of B-homo palmatine (11a) and berberine (11b) derivatives, which were synthesized from 3,4-dimethoxybenzaldehyde (1a) and benzo[d][1,3]dioxole-5-carbaldehyde (1b) in nine steps in 13.8 and 16.9 % overall yields, respectively. A number of other new B-homo palmatine and berberine derivatives were also prepared. These derivatives display good inhibitory activity against p300 HAT; compound 12a manifests the most potent inhibition with an IC50 value of 0.42 μm. Cell-based assays revealed that 12a exhibits certain inhibitory activity against HCG27, HT1080, and Z-138 cell lines, and no visible activity towards other cancer cell lines tested, reflecting that 12a has low cytotoxicity and acts against some types of cancer cells.

High B ring berberine and palmatine derivative synthesis and as the use of reducing blood sugar (by machine translation)

The present invention provides a new class of high B ring berberine and palmatine derivative, as shown in the structural formula is shown as: The invention also provides a high B ring berberine and palmatine derivative of preparation and use. The potency test Certificate, the compounds of the invention having good in-vitro hypoglycemic effect, part of the superior to the berberine hydrochloride positive control. The invention high B ring berberine and palmatine derivative potency is prominent, there may be clinical provides a new choice of drug use for. (by machine translation)