67853-03-6

Usage

Uses

Used in Pharmaceutical Industry:
3-Hydroxymethyl-Benzoic Acid Methyl Ester is used as a synthetic intermediate for the preparation of N-acylhydrazone derivatives, which serve as lactate dehydrogenase A inhibitors. These inhibitors are of interest in the development of pharmaceuticals targeting LDH-A, an enzyme implicated in various diseases, including cancer.
In the context of the provided materials, the primary application of 3-Hydroxymethyl-Benzoic Acid Methyl Ester is in the pharmaceutical industry, where it plays a crucial role in the synthesis of compounds with potential therapeutic applications. Its versatility in chemical reactions allows for the creation of new derivatives that can target specific enzymes, such as lactate dehydrogenase A, offering opportunities for the development of novel treatments.

InChI:InChI=1/C9H10O3/c1-12-9(11)8-4-2-3-7(5-8)6-10/h2-5,10H,6H2,1H3

Upstream product

• 1877-71-0 benzene 1,3-dicarboxylic acid monomethyl ester 
• 1129-28-8 3-methoxycarbonylbenzyl bromide 
• 660416-36-4 3-fluoro-5-(methoxycarbonyl)benzoic acid 
• 634-65-1 2,4-dimethylbenzene-1,3-diol 
• 52178-50-4 Methyl 3-formylbenzoate 
• 99-36-5 1-methoxycarbonyl-3-methylbenzene 
• 121-91-5 isophthalic acid 
• 67-56-1 methanol 
• 28286-79-5 3-(Hydroxymethyl)benzoic acid 
• 1459-93-4 dimethyl Isophthalate 

Downstream Products

• 95570-52-8 3-(N,N'-Diisopropyl-carbamimidoyloxymethyl)-benzoic acid methyl ester 
• 660416-38-6 methyl 3-fluoro-5-methylbenzoate 
• 96534-02-0 3-(diethyoxyphosphorylmethyl)benzoic acid methyl ester 
• 1268245-10-8 (-)-3-(2-(2-chloro-4-((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methoxy)phenyl)cyclopropyl)benzoic acid 
• 1169947-65-2 C₁₆H₁₃ClO₃ 
• 1268245-69-7 C₂₂H₂₇ClO₃Si 
• 1263281-96-4 C₁₇H₁₅ClO₃ 
• 1268246-69-0 3-(2-(2-chloro-4-((5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)isoxazol-4-yl)methoxy)phenyl)cyclopropyl)-benzoic acid 
• 1268245-12-0 4-(4-((4-(2-(3-carboxyphenyl)cyclopropyl)-3-chlorophenoxy)methyl)-5-cyclopropylisoxazol-3-yl)-3,5-dichloropyridine 1-oxide 
• 1268245-13-1 3-(2-(2-chloro-4-((1-(2,6-dichlorophenyl)-4-isopropyl-1H-1,2,3-triazol-5-yl)methoxy)phenyl)cyclopropyl)benzoic acid 
• 1268245-11-9 3-(2-(2-chloro-4-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)phenyl)cyclopropyl)benzoic acid 
• 1410799-93-7 C₁₀H₁₄O₃ 
• 1070344-97-6 methyl 3-(tert-butyldimethylsilyloxymethyl)benzoate 
• 1515-87-3 methyl 3-(methoxymethyl)benzoate 

Relevant academic research and scientific papers

ANTIMALARIAL AGENTS

Provided are methods of treating malaria comprising administration of compounds of Formula (I) or a pharmaceutically acceptable salt thereof, to a subject in need thereof, wherein the variables are as defined herein. Also provided are uses of the compounds of Formula (I), as defined herein, for treating a Plasmodium infection, and for treating malaria. Also provided are methods of treatment further comprising administration of one or more additional anti-malarial compounds.

ALK5 INHIBITORS

The present disclosure provides inhibitors of activin receptor-like kinase 5 (ALK5). Also disclosed are methods to modulate the activity of ALK5 and methods of treatment of disorders mediated by ALK5.

MATRIX METALLOPROTEINASE (MMP) INHIBITORS AND METHODS OF USE THEREOF

Hydantoin based compounds useful as inhibitors of matrix metalloproteinases (MMPs), particularly macrophage elastase (MMP-12) are described. Also described are related compositions and methods of using the compounds to inhibit MMP-12 and treat diseases mediated by MMP-12, such as asthma, chronic obstructive pulmonary disease (COPD), emphysema, acute lung injury, idiopathic pulmonary fibrosis (IPF), sarcoidosis, systemic sclerosis, liver fibrosis, nonalcoholic steatohepatitis (NASH), arthritis, cancer, heart disease, inflammatory bowel disease (IBD), acute kidney injury (AKI), chronic kidney disease (CKD), Alport syndrome, and nephritis.

Bisubstrate inhibitors of nicotinamide N-methyltransferase (NNMT) with enhanced activity

Nicotinamide N-methyltransferase (NNMT) catalyzes the methylation of nicotinamide to form N-methylnicotinamide. Overexpression of NNMT is associated with a variety of diseases, including a number of cancers and metabolic disorders, suggesting a role for NNMT as a potential therapeutic target. By structural modification of a lead NNMT inhibitor previously developed in our group, we prepared a diverse library of inhibitors to probe the different regions of the enzyme's active site. This investigation revealed that incorporation of a naphthalene moiety, intended to bind the hydrophobic nicotinamide binding pocket via π-πstacking interactions, significantly increases the activity of bisubstrate-like NNMT inhibitors (half-maximal inhibitory concentration 1.41 μM). These findings are further supported by isothermal titration calorimetry binding assays as well as modeling studies. The most active NNMT inhibitor identified in the present study demonstrated a dose-dependent inhibitory effect on the cell proliferation of the HSC-2 human oral cancer cell line.

Palladium Catalysis Enables Benzylation of α,α-Difluoroketone Enolates

A palladium-catalyzed decarboxylative benzylation reaction of α,α-difluoroketone enolates is reported, in which the key C(α)?C(sp3) bond is generated by reductive elimination from a palladium intermediate. The transformation provides convergent access to α-benzyl-α,α-difluoroketone-based products, and should be useful for accessing biological probes.

Identification of N-acylhydrazone derivatives as novel lactate dehydrogenase A inhibitors

Abstract Glycolysis is drastically increased in tumors and it is the main route to energy production with a minor use of oxidative phosphorylation. Among the key enzymes in the glycolytic process, LDH is emerging as one of the most interesting targets for the development of new inhibitors. In this context, in the present work, we carried out a virtual screening procedure followed by chemical modifications of the identified structures according to a "hit-to-lead" process. The effects of the new molecules were preliminary probed against purified human LDH-A. The compounds active at low micromolar level were additionally characterized for their activity on some cellular metabolic processes by using Raji human cell line. Within the series, 1 was considered the best candidate, and a more detailed characterization of its biological properties was performed. In Raji cells exposed to compound 1 we evidenced the occurrence of effects usually observed in cancer cells after LDH-A inhibition: reduced lactate production and NAD/NADH ratio, apoptosis. The flow cytometry analysis of treated cells also showed cell cycle changes compatible with effects exerted at the glycolytic level. Finally, in agreement with the data obtained with other inhibitors or by silencing LDH-A expression, compound 1 was found to increase Raji cells response to some commonly used chemotherapeutic agents. Taken together, all these finding are in support of the LDH-A inhibiting activity of compound 1.

HETEROARYL COMPOUNDS USEFUL AS INHIBITORS OF SUMO ACTIVATING ENZYME

Disclosed are compounds of formula (I): or a pharmaceutically acceptable salt thereof; wherein Y, Ra, Ra', Rc, Rf, X2, Rd, Rd', Re, Re', m, and G have the values described herein and stereochemical configurations depicted at asterisked positions indicate absolute stereochemistry, useful as inhibitors of Sumo Activating Enzyme (SAE). Further provided are pharmaceutical compositions comprising a compound of the disclosure and methods of using the compositions in the treatment of proliferative, inflammatory, cardiovascular and neurodegenerative diseases or disorders.

Electrochemical direct carboxylation of benzyl alcohols having an electron-withdrawing group on the phenyl ring: One-step formation of phenylacetic acids from benzyl alcohols under mild conditions

Electrochemical direct carboxylation of benzyl alcohols having an electron-withdrawing group on the phenyl ring was successfully carried out by constant current electrolysis using an undivided cell equipped with a platinum plate cathode and a magnesium rod anode in DMF in the presence of carbon dioxide. Reductive cleavage of the C-O bond followed by fixation of carbon dioxide efficiently took place at the benzylic position without any additive to give the corresponding phenylacetic acids in good yields in one step under neutral and mild conditions.

Synthesis and evaluation of isoleucine derived angiotensin II AT 2 receptor ligands

Sixteen new C-terminally modified analogues of 2, a previously described potent and selective AT2R ligand, were designed, synthesized and evaluated for their affinity to the AT2R receptor. The introduction of large, hydrophobic substituents was shown to be beneficial and the most active compound (17, Ki = 8.5 μM) was over 12-times more potent than the lead compound 2.

Electrophilicity and nucleophilicity of commonly used aldehydes

The present approach for determining the electrophilicity (E) and nucleophilicity (N) of aldehydes includes a kinetic study of KMNO4 oxidation and NaBH4 reduction of aldehydes. A transition state analysis of the KMNO4 promoted aldehyde oxidation reaction has been performed, which shows a very good correlation with experimental results. The validity of the experimental method has been tested using the experimental activation parameters of the two reactions. The utility of the present approach is further demonstrated by the theoretical versus experimental relationship, which provides easy access to E and N values for various aldehydes and offers an at-a-glance assessment of the chemical reactivity of aldehydes in various reactions. the Partner Organisations 2014.