1486-53-9

Usage

Uses

Used in Pharmaceutical Industry:
4-Benzyloxy-3-methoxybenzoic acid is used as a key intermediate in the synthesis of Hsp90 inhibitors, which are analogs of the natural compound Epigallocatechin gallate (EGCG). These inhibitors play a crucial role in targeting and disrupting the function of the Hsp90 protein, a molecular chaperone involved in the stabilization and activation of various client proteins, including those implicated in cancer and other diseases.
Additionally, 4-Benzyloxy-3-methoxybenzoic acid is utilized in the preparation of vanillates, which are compounds exhibiting cytostatic properties towards cancer cells that are resistant to pro-apoptotic stimuli. These vanillates can potentially enhance the effectiveness of cancer treatments by targeting cells that are less susceptible to conventional therapies.

InChI:InChI=1/C15H14O4/c1-18-14-9-12(15(16)17)7-8-13(14)19-10-11-5-3-2-4-6-11/h2-9H,10H2,1H3,(H,16,17)/p-1

Upstream product

• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 38768-62-6 methyl (2-methoxyphenoxy) ethanoate 
• 130471-75-9 ο-Benzoyloxy-phloracetophenon 
• 116512-03-9 4-Benzyloxy-3-methoxy-benzoesaeureanhydrid 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 100-44-7 benzyl chloride 
• 185033-64-1 ethyl 4-benzyloxy-3-methoxybenzoate 
• 617-05-0 ethyl vanillate 
• 121-33-5 vanillin 
• 3943-74-6 4-hydroxy-3-methoxybenzoic acid methyl ester 
• 100-39-0 benzyl bromide 
• 7732-18-5 water 
• 56441-97-5 methyl 4-(benzyloxy)-3-methoxybenzoate 
• 91203-74-6 4-benzyloxy-3-methoxybenzoic acid benzyl ester 

Downstream Products

• 849795-68-2 methyl (2S)-N-(4-benzyloxy-3-methoxybenzoyl)pyrrolidin-2-carboxylate 
• 56441-97-5 methyl 4-(benzyloxy)-3-methoxybenzoate 
• 64154-78-5 4-benzyloxy-5-methoxy-2-nitrobenzoyl chloride 
• 127810-77-9 (2S)-N-[4-benzyloxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethyl dithioacetal 
• 64154-79-6 (2S)-N-(4-benzyloxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxylic acid 
• 140647-02-5 (2S)-N-(4-hydroxy-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal 
• 140693-22-7 (S)-1-(4-(benzyloxy)-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carbaldehyde 
• 140646-99-7 (S)-methyl 1-(4-(benzyloxy)-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxylate 
• 175409-49-1 methyl-(2S)-N-[4-hydroxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxylate 
• 482378-36-9 1-{4-[3-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-propoxy]-5-methoxy-2-nitro-benzoyl}-pyrrolidine-2-carboxylic acid methyl ester 
• 482378-37-0 1-{4-[4-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-butoxy]-5-methoxy-2-nitro-benzoyl}-pyrrolidine-2-carboxylic acid methyl ester 
• 482378-31-4 2-(3-{5-amino-4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-phenoxy}-propyl)-benzo[de]isoquinoline-1,3-dione 
• 482378-38-1 1-{4-[5-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-pentyloxy]-5-methoxy-2-nitro-benzoyl}-pyrrolidine-2-carboxylic acid methyl ester 
• 482378-25-6 2-(3-{4-[2-(bis-ethylsulfanyl-methyl)-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-propyl)-benzo[de]isoquinoline-1,3-dione 

Relevant academic research and scientific papers

Transition Metal-Free Regioselective Remote C?H Bond 2,2,2-Trifluoroethoxylation of 8-Aminoquinoline Derivatives at the C5 Position

The regioselective 2,2,2-trifluoroethoxylation at the C5 position of amides derived from the 8-aminoquinoline has been developed. In the presence of PIDA, an unprecedented and undirected transition metal-free transformation was achieved using the readily available and appealing 2,2,2-trifluoroethanol as the fluorinated source. The selective distal 2,2,2-trifluoroethoxylation of an array of amides was achieved in moderate to good yields (12 examples, up to 61 % yield). This approach provided efficient access to high-value added fluorinated quinoline derivatives, key building blocks for bulk and fine chemical industry.

Synthesis and antitumor activity of novel pyridoxine-based structural analogs of saccharumoside-B

A series of 11 new pyridoxine-based structural analogs of saccharumoside-B were obtained using original synthetic approach. Antitumor activity of these compounds against nine human tumor cell lines (MCF-7, MDA-MB-231, A-498, SNB-19, M-14, NCI-H322M, HCT-115, HCT-116, and PC-3) was studied, and cytotoxic activity to three normal (HEK-293, Chang Liver, and MSC) cell lines was evaluated. Among the synthesized compounds, 12d, 12e, 13b, 13d, 13e, and 14 exhibited the highest antitumor activity, comparable to that of camptothecin and doxorubicin, but with significantly increased selectivity toward tumor cells. [Figure not available: see fulltext.]

VISUAL DETECTION OF PBD INDUCED DNA CROSSLINKS

The present invention relates to the field of oncology, laboratory tools and methods, and especially anti-tumor DNA crosslinking agents. Most patients with advanced solid tumors develop resistance to chemotherapy due to the ability of cancer cells to repair or tolerate sustained DNA damages. The inventors showed that the compounds according to the present invention allow the detection and visualization of alkylated DNA damages induced by PBDs without altering their DNA crosslinking ability. This enables the study of the effect and properties of PBDs. In particular, the present invention relates new derivates of PBD molecules and their synthesis. The present invention also relates to a method for visualizing DNA crosslinking; to a method for assessing the resistance of a tumor to a crosslinking agent and to a method for identifying a molecule or treatment for improving the efficiency of a crosslinking agent.

Synthesis and evaluation of new sesamol-based phenolic acid derivatives with hypolipidemic, antioxidant, and hepatoprotective effects

The objective of this study is to synthesize a series of sesamol-based phenolic acid derivatives, which were designed by combination principle. The hypolipidemic activity of all these compounds was preliminarily screened by acute hyperlipidemic mice model induced by Triton WR 1339, in which compound T6 exhibited more significant reducing plasma TG and TC than fenofibrate. Compound T6 was also found to obviously decrease TG and TC both in the plasma and hepatic tissue of high-fat-diet-induced hyperlipidemic mice. Moreover, T6 showed hepatoprotective effects, which remarkable amelioration in characteristic liver enzymes was examined and the histopathological observation displayed that compound T6 inhibited lipids accumulation in the hepatic. The levels of PPAR-α receptor related to lipids metabolism in hepatic tissue were upregulated after T6 treatment. Other potent effects of T6 such as antioxidant and anti-inflammatory activity were also observed. On the bases of these findings, compound T6 may serve as an effective hypolipidemic and hepatoprotective agent. [Figure not available: see fulltext.]

CROSS-LINKED PYRROLOBENZODIAZEPINE DIMER (PBD) DERIVATIVE AND ITS CONJUGATES

A novel cross-linked cytotoxic agents, pyrrolobenzo-diazepine dimer (PBD) derivatives, and their conjugates to a cell-binding molecule, a method for preparation of the conjugates and the therapeutic use of the conjugates.

CONJUGATION LINKERS CONTAINING 2,3-DIAMINOSUCCINYL GROUP

Provided is a conjugate of a cytotoxic drug/molecule to a cell-binding molecule with a bis-linker (adual-linker) containing a 2, 3-diaminosuccinyl group. It also relates to preparation of the conjugate of a cytotoxic drug/molecule to a cell-binding molecule with the bis-linker, particularly when the drug having functional groups of amino, hydroxyl, diamino, amino-hydroxyl, dihydroxyl, carboxyl, hydrazine, aldehyde and thiol for conjugation with the bis-linker in a specific manner, as well as the therapeutic use of the conjugates.

Method For Producing Low Molecular Weight Aromatic Lignin-Derived Compounds

The present invention relates to a method for producing one or more low molecular weight aromatic lignin-derived compounds. The method preferably comprises providing lignocellulosic material, subjecting the lignocellulosic material to a pulping process, separating pulp to provide a substantially pulp-free process stream comprising a modified lignin-derived component, isolating the modified lignin-derived component, subjecting the isolated modified lignin-derived component to a decomposition step comprising oxidative cracking (cracking and oxidizing) or reducing under the influence of a catalyst or electro-oxidation, and subjecting the resulting products to an isolation step, to provide a low molecular weight aromatic lignin-derived compound. Said compound may be further modified, e.g. by annulation. The inventive method preferably comprises further oxidizing said compound to a redox active compound. Additionally, the present invention relates to compounds obtainable by the inventive method and to an assembly for carrying out the inventive method. Furthermore, the present invention refers to a method for providing an existing pulp and/or paper manufacturing plant with said assembly.

AMINATED LIGNIN-DERIVED COMPOUNDS AND USES THEREOF

The present invention relates to novel lignin-derived compounds and compositions comprising the same and their use as redox flow battery electrolytes. The invention further provides a method for preparing said compounds and compositions as well as a redox flow battery comprising said compounds and compositions. Additionally, an assembly for carrying out the inventive method is provided.

Discovery of an Orally Bioavailable and Central Nervous System (CNS) Penetrant mGlu7 Negative Allosteric Modulator (NAM) in Vivo Tool Compound: N-(2-(1 H-1,2,4-triazol-1-yl)-5-(trifluoromethoxy)phenyl)-4-(cyclopropylmethoxy)-3-methoxybenzamide (VU6012962)

Herein, we report the discovery of a new, orally bioavailable and CNS-penetrant metabotropic glutamate receptor 7 (mGlu7) negative allosteric modulator (NAM) that achieves exposure in cerebral spinal fluid (CSF) 2.5× above the in vitro IC50 at minimum effective doses (MEDs) of 3 mg/kg in preclinical anxiety models.

CONJUGATION OF A CYTOTOXIC DRUG WITH BIS-LINKAGE

What provided is the conjugation of cytotoxic to a cell-binding molecule with a bis-linker(dual-linker) as shown in Formula (I). It provides bis-linkage methods of making a conjugate of a cytotoxic drug molecule to a cell-binding agent in a specific manner. It also relates to application of the conjugates for the treatment of a cancer, or an autoimmune disease, or an infectious disease.