52178-50-4

Usage

Uses

Used in Medical Applications:
Methyl 3-formylbenzoate is used as a reagent for the detection of amyloid deposits in patients with various forms of amyloidosis. Amyloidosis is a group of rare diseases caused by the abnormal accumulation of amyloid proteins in tissues and organs, leading to progressive organ dysfunction. Methyl 3-formylbenzoate's ability to detect these deposits aids in the diagnosis and monitoring of the disease.
Used in Pharmaceutical Industry:
Methyl 3-formylbenzoate is used as a key intermediate in the synthesis of several bioactive compounds, which have potential applications in the pharmaceutical industry. Some of these compounds include:
1. Meso-tetrakis(3-carboxyphenyl)porphyrin: Methyl 3-formylbenzoate is synthesized through a condensation reaction with pyrrole and has potential applications in the development of new drugs and therapies.
2. Methyl 3-[4-(1-methyl-3-phenylureido)phenylaminomethyl]benzoate: Methyl 3-formylbenzoate exhibits moderate SENP1 protease inhibition activity, which may be useful in the development of treatments for diseases associated with abnormal protein degradation.
3. An N-methyl-sulfonylhydrazone derivative: Methyl 3-formylbenzoate is being investigated as a potential anti-diabetic agent with good plasma stability, which could lead to improved treatment options for patients with diabetes.

InChI:InChI=1/C9H8O3/c1-12-9(11)8-4-2-3-7(5-8)6-10/h2-6H,1H3

Upstream product

• 67-56-1 methanol 
• 619-21-6 m-formylphenyl benzoic acid 
• 13531-48-1 methyl 3-cyanobenzoate 
• 201230-82-2 carbon monoxide 
• 618-91-7 methyl 3-iodo-benzoate 
• 93071-65-9 3-methoxycarbonyl benzylamine 
• 67853-03-6 methyl 3-(hydroxymethyl)benzoate 
• 4518-10-9 Methyl 3-aminobenzoate 
• 74-88-4 methyl iodide 
• 70760-00-8 3-carbomethoxybenzaldiacetate 
• 7664-93-9 sulfuric acid 
• 1459-93-4 dimethyl Isophthalate 
• 1877-71-0 benzene 1,3-dicarboxylic acid monomethyl ester 
• 99-36-5 1-methoxycarbonyl-3-methylbenzene 

Downstream Products

• 52178-52-6 3-(2-methyl-5-oxo-oxazol-4-ylidenemethyl)-benzoic acid methyl ester 
• 1027736-41-9 7-Methoxy-2-(3-methoxycarbonylbenzylidene)-3,4-dihydro-1(2H)-naphthalenone 
• 175691-34-6 C₄₃H₄₆N₂O₅ 
• 208450-88-8 3-carbomethoxybenzylidene-3-carbomethoxybenzylamine 
• 208450-87-7 3-[(Z)-Benzylimino-methyl]-benzoic acid methyl ester 
• 1877-71-0 benzene 1,3-dicarboxylic acid monomethyl ester 
• 203940-17-4 methyl 3-[(E)-2-(7-chloro-2-quinolyl)vinyl]benzoate 
• 1026381-14-5 3-(1-carboxymethyl-3-chloro-5-isopropylamino-6-oxo-1,6-dihydro-pyrazin-2-yl)-benzoic acid methyl ester 
• 1027488-09-0 3-(1-benzyloxycarbonylmethyl-3-chloro-5-isopropylamino-6-oxo-1,6-dihydro-pyrazin-2-yl)-benzoic acid methyl ester 

Relevant academic research and scientific papers

NOVEL HETEROARYL-TRIAZOLE COMPOUNDS AS PESTICIDES

The present invention relates to novel heteroaryl-triazole and heteroaryl-tetrazole compounds of the general formula (I), in which the structural elements R1, R2, R3, R4 and R5 have the meaning given in the description, to formulations and compositions comprising such compounds and for their use in the control of animal pests including arthropods and insects in plant protection and to their use for control of ectoparasites on animals.

NOVEL HETEROARYL-TRIAZOLE COMPOUNDS AS PESTICIDES

The present invention relates to novel heteroaryl-triazole compounds of the general formula (I), in which the structural elements X, R1, R2, R3, R4 and R5 have the meaning given in the description, to

Potassium Poly(Heptazine Imide): Transition Metal-Free Solid-State Triplet Sensitizer in Cascade Energy Transfer and [3+2]-cycloadditions

Polymeric carbon nitride materials have been used in numerous light-to-energy conversion applications ranging from photocatalysis to optoelectronics. For a new application and modelling, we first refined the crystal structure of potassium poly(heptazine imide) (K-PHI)—a benchmark carbon nitride material in photocatalysis—by means of X-ray powder diffraction and transmission electron microscopy. Using the crystal structure of K-PHI, periodic DFT calculations were performed to calculate the density-of-states (DOS) and localize intra band states (IBS). IBS were found to be responsible for the enhanced K-PHI absorption in the near IR region, to serve as electron traps, and to be useful in energy transfer reactions. Once excited with visible light, carbon nitrides, in addition to the direct recombination, can also undergo singlet–triplet intersystem crossing. We utilized the K-PHI centered triplet excited states to trigger a cascade of energy transfer reactions and, in turn, to sensitize, for example, singlet oxygen (1O2) as a starting point to synthesis up to 25 different N-rich heterocycles.

Cobalt(ii)-catalyzed benzylic oxidations with potassium persulfate in TFA/TFAA

A cobalt-catalyzed C(sp3)-H oxygenation reaction to furnish aldehyde was herein reported. This transformation demonstrated high chemo-selectivity, and tolerated various methylarenes bearing electron-withdrawing substituents. This reaction provided rapid access to diverse aldehydes form methylarenes. Notably, TFA/TFAA was used for the first time as a mixed solvent in cobalt-catalyzed oxygenation of benzylic methylenes.

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.

Design, Synthesis, and Biological Evaluation of Novel Allosteric Protein Disulfide Isomerase Inhibitors

Protein disulfide isomerase (PDI) is responsible for nascent protein folding in the endoplasmic reticulum (ER) and is critical for glioblastoma survival. To improve the potency of lead PDI inhibitor BAP2 ((E)-3-(3-(4-hydroxyphenyl)-3-oxoprop-1-en-1-yl)benzonitrile), we designed and synthesized 67 analogues. We determined that PDI inhibition relied on the A ring hydroxyl group of the chalcone scaffold and cLogP increase in the sulfonamide chain improved potency. Docking studies revealed that BAP2 and analogues bind to His256 in the b′ domain of PDI, and mutation of His256 to Ala abolishes BAP2 analogue activity. BAP2 and optimized analogue 59 have modest thiol reactivity; however, we propose that PDI inhibition by BAP2 analogues depends on the b′ domain. Importantly, analogues inhibit glioblastoma cell growth, induce ER stress, increase expression of G2M checkpoint proteins, and reduce expression of DNA repair proteins. Cumulatively, our results support inhibition of PDI as a novel strategy to treat glioblastoma.

Deoxygenative Deuteration of Carboxylic Acids with D2O

We report a general, practical, and scalable means of preparing deuterated aldehydes from aromatic and aliphatic carboxylic acids with D2O as an inexpensive deuterium source. The use of Ph3P as an O-atom transfer reagent can facilitate the deoxygenation of aromatic acids, while Ph2POEt is a better O-atom transfer reagent for aliphatic acids. The highly precise deoxygenation of complex carboxylic acids makes this protocol promising for late-stage deoxygenative deuteration of natural product derivatives and pharmaceutical compounds.

Discovery and preliminary structure–activity relationship of 1H-indazoles with promising indoleamine-2,3-dioxygenase 1 (IDO1) inhibition properties

Indoleamine 2,3-dioxygenase 1 (IDO1)-mediated kynurenine pathway of tryptophan degradation is identified as an important immune effector pathway in the tumor cells to escape a potentially effective immune response. IDO1 is an attractive target for anticancer therapy and the discovery of IDO1 inhibitors has been intensely ongoing in both academic research laboratories and pharmaceutical organizations. Our study discovered that 1H-indazole was a novel key pharmacophore with potent IDO1 inhibitory activity. A series of new 1H-indazole derivatives were synthesized and determined the enzyme inhibitory activities, and the compound 2g exhibited the highest activity with an IC50value of 5.3 μM. The structure–activity relationships (SARs) analysis of the 1H-indazole derivatives as novel IDO1 inhibitors indicated that the 1H-indazole scaffold is necessary for IDO1 inhibition, and the substituent groups at the both 4-position and 6-position largely affect inhibitory activity. The docking model exhibited that the effective interactions of 1H-indazoles with ferrous ion of heme and key residues of hydrophobic Pocket A and B ensured the IDO1 inhibitory activities. The study suggested that the 1H-indazole was a novel interesting scaffold for IDO inhibition for further development.

Diphosphino-functionalised MCM-41-supported palladium complex: An efficient and recyclable catalyst for the formylation of aryl halides

The heterogeneous formylation of aryl halides with HCO2Na at atmospheric pressure by carbon monoxide was readily achieved in the presence of the diphosphino-functionalised MCM-41-supported palladium complex in DMF to afford the corresponding aromatic aldehydes in good to excellent yields. This heterogeneous palladium catalyst can be recovered by simple filtration and reused 10 times without any loss of activity.