72730-39-3

Usage

Uses

Used in Organic Synthesis:
2-Mercapto-1,3-benzoxazole-5-carboxylic acid methyl ester is used as a building block in organic synthesis for the creation of various organic compounds. Its unique structure and functional groups allow for a wide range of chemical reactions, making it a valuable component in the synthesis of complex molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Mercapto-1,3-benzoxazole-5-carboxylic acid methyl ester is used as a key intermediate in the development of new drugs. Its thiol group and other functional groups enable the formation of diverse chemical entities with potential therapeutic properties. Researchers can exploit its reactivity to design and synthesize novel pharmaceutical compounds with improved efficacy and selectivity.
Used in Chemical Reactions:
2-Mercapto-1,3-benzoxazole-5-carboxylic acid methyl ester is utilized in various chemical reactions due to its reactive thiol group and other functional groups. It can participate in a range of reactions, such as nucleophilic substitutions, esterification, and amide bond formations, among others. This makes it a useful reagent in the synthesis of a variety of chemical products.
Used in Solvent Systems:
The solubility of 2-Mercapto-1,3-benzoxazole-5-carboxylic acid methyl ester in organic solvents is advantageous for its use in solvent systems. It can be employed as a solubilizing agent or as a component in the formulation of various chemical processes that require organic solvents, enhancing the efficiency and effectiveness of these processes.

Upstream product

• 75-15-0 carbon disulfide 
• 536-25-4 methyl 3-amino-4-hydroxybenzoate 
• 140-89-6 potassium ethyl xanthogenate 
• 1571-72-8 3-amino-4-hydroxybenzoic acid 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 463-71-8 thiophosgene 
• 67-56-1 methanol 
• 7341-98-2 2-thioxo-2,3-dihydrobenzo[d]oxazole-5-carboxylic acid 

Downstream Products

• 72730-57-5 3-(4-phenyl-piperazin-1-ylmethyl)-2-thioxo-2,3-dihydro-benzooxazole-5-carboxylic acid methyl ester 
• 72730-50-8 N-{4-[(5-methoxycarbonyl-2-thioxo-benzooxazol-3-ylmethyl)-amino]-benzoyl}-glutamic acid dimethyl ester 
• 72730-40-6 3-hydroxymethyl-2-thioxo-2,3-dihydro-benzooxazole-5-carboxylic acid methyl ester 
• 72730-52-0 3-[4-(4,6-dimethyl-pyrimidin-2-ylsulfamoyl)-anilinomethyl]-2-thioxo-2,3-dihydro-benzooxazole-5-carboxylic acid methyl ester 
• 72730-41-7 5-Carbomethoxy-3-acetylbenzoxazolin-2-thione 
• 72730-47-3 3-(4-chloro-anilinomethyl)-2-thioxo-2,3-dihydro-benzooxazole-5-carboxylic acid methyl ester 
• 72730-48-4 3-(4-methoxy-anilinomethyl)-2-thioxo-2,3-dihydro-benzooxazole-5-carboxylic acid methyl ester 
• 72730-46-2 3-anilinomethyl-2-thioxo-2,3-dihydro-benzooxazole-5-carboxylic acid methyl ester 
• 72730-49-5 3-(4-ethoxy-anilinomethyl)-2-thioxo-2,3-dihydro-benzooxazole-5-carboxylic acid methyl ester 
• 72730-51-9 3-(4-ethoxycarbonyl-anilinomethyl)-2-thioxo-2,3-dihydro-benzooxazole-5-carboxylic acid methyl ester 
• 54120-92-2 methyl 2-chloro-1,3-benzoxazole-5-carboxylate 
• 1357026-04-0 methyl 3-(3-phenylpropanoyl)-2,3-dihydro-2-thioxobenzo[d]oxazole-5-carboxylate 
• 213684-90-3 methyl 2-((6-((2,6-diisopropylphenyl)amino)-6-oxohexyl)thio)benzo[d]oxazole-5-carboxylate 
• 213684-93-6 N-(2,6-diisopropylphenyl)-6-((5-((N,N-dimethylamino)methyl)benzo[d]oxazol-2-yl)thio)hexanamide 

Relevant academic research and scientific papers

Tunable Amine-Reactive Electrophiles for Selective Profiling of Lysine

Proteome profiling by activated esters identified >9000 ligandable lysines but they are limited as covalent inhibitors due to poor hydrolytic stability. Here we report our efforts to design and discover a new series of tunable amine-reactive electrophiles (TAREs) for selective and robust labeling of lysine. The major challenges in developing selective probes for lysine are the high nucleophilicity of cysteines and poor hydrolytic stability. Our work circumvents these challenges by a unique design of the TAREs that form stable adducts with lysine and on reaction with cysteine generate another reactive electrophiles for lysine. We highlight that TAREs exhibit substantially high hydrolytic stability as compared to the activated esters and are non-cytotoxic thus have the potential to act as covalent ligands. We applied these alternative TAREs for the intracellular labeling of proteins in different cell lines, and for the selective identification of lysines in the human proteome on a global scale.

TLR2 MODULATOR COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF

The present disclosure relates to compounds which modulate the activity of Toll-like receptor (TLR) proteins, including agonists or activators, partial agonists, and antagonists. Of particular interest of compounds that modulate the activity of TLR2, as well as methods of using such compounds to treat cancer and other disorders associated with a TLR2 pathway.

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same. The compounds include an IRAK binding moiety capable of binding to IRAK4 and a degradation inducing moiety (DIM). The DIM could be DTM a ligase binding moiety (LBM) or lysine mimetic. The compounds could be useful as IRAK protein kinase inhibitors and applied to IRAK mediated disorders.

The discovery and optimization of a series of 2-aminobenzoxazole derivatives as ChemR23 inhibitors

A structural class of 2-aminobenzoxazole derivatives possessing biphenyltetrazole was discovered to be potent human ChemR23 inhibitors. We initially tried to improve the potency of compound 1, which was found through in-house screening using the human pla

Design, synthesis and pharmacology of aortic-selective acyl-CoA: Cholesterol O-acyltransferase (ACAT/SOAT) inhibitors

We describe our molecular design of aortic-selective acyl-coenzyme A:cholesterol O-acyltransferase (ACAT, also abbreviated as SOAT) inhibitors, their structure–activity relationships (SARs) and their pharmacokinetic (PK) and pharmacological profiles. The connection of two weak ligands—N-(2,6-diisopropylphenyl)acetamide (50% inhibitory concentration [IC50] = 8.6 μM) and 2-(methylthio)benzo[d]oxazole (IC50 = 31 μM)—via a linker comprising a 6 methylene group chains yielded a highly potent molecule, 9-(benzo[d]oxazol-2-ylthio)-N-(2,6-diisopropylphenyl)nonanamide (3h) that exhibited high potency (IC50 = 0.004 μM) toward aortic ACAT. This head-to-tail design made it possible to markedly enhance the activity to 2150- to 7750-fold and to discriminate the isoform-selectivity based on the double-induced fit mechanism. At doses of 1 and 3 mg/kg, 3h significantly decreased the lipid-accumulation areas in the aortic arch to 74 and 69%, respectively without reducing the plasma total cholesterol level in high fat- and cholesterol-fed F1B hamsters. Here, we demonstrate the antiatherosclerotic effect of 3h in vivo via its direct action on aortic ACAT and its powerful modulator of cholesterol level. This molecule is a potential therapeutic agent for the treatment of diseases involving ACAT-1 overexpression.

ANTIBIOTIC COMPOUNDS

The present invention relates to antibiotic compounds of formula (I), to compositions containing these compounds and to methods of treating bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Gram-positive and/or Gram-negative bacteria, and in particular in the treatment of infection with, and diseases caused by, Neisseria gonorrhoeae.

Design of benzimidazole- and benzoxazole-2-thione derivatives as inhibitors of bacterial hyaluronan lyase

Bacterial hyaluronan lyases (Hyal) degrade hyaluronan, an important component of the extracellular matrix, and are involved in microbial spread. Hyal inhibitors may serve as tools to study the role of the enzyme, its substrates and products in the course of bacterial infections. Moreover, such enzyme inhibitors are potential candidates for antibacterial combination therapy. Based on crystal structures of Streptococcus pneumoniae Hyal in complex with a hexasaccharide substrate and with different inhibitors, 1-acylated benzimidazole-2-thiones and benzoxazole-2-thiones were derived as new leads for the inhibition of Streptococcus agalactiae strain 4755 Hyal. Structure-based optimization led to N-(3-phenylpropionyl)benzoxazole-2-thione, one of the most potent compounds known to date (IC50 values: 24 μM at pH 7.4, 15 μM at pH 5). Among the 27 new derivatives, other N-acylated benzimidazoles and benzoxazoles are just as active at pH 7.4, but not at pH 5. The results support a binding mode characterized by interactions with residues in the catalytic site and with a hydrophobic patch.

PIPERIDINE DERIVATIVES OR SALTS THEREOF

[Problem] To provide a compound which can be used for treating diseases in which a calcium sensing receptor (CaSR) participates, particularly hyperparathyroidism. [Means for Resolution] It was found that a novel piperidine derivative which is characterized in that one of a 3-position and a 4-position is substituted with an aminomethyl group substituted with an arylalkyl group or the like and the other position is substituted with aryl, heteroaryl or the like, or a salt thereof, has an excellent CaSR agonistic regulatory action, and also has excellent selectivity with a CYP2D6 inhibitory action having a possibility of causing drug interaction. Based on the above, this novel piperidine derivative is useful as a therapeutic agent for diseases in which CaSR participates (hyperparathyroidism, renal osteodystrophy, hypercalcemia, and the like).

BENZOTHIAZOLE AND BENZOOXAZOLE DERIVATIVES AND METHODS OF USE

Compounds of formula (I) are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions of compounds of formula (I), methods for using such compounds and compositions, and a process for preparing the compounds.

Facile rearrangements of alkynylamino heterocycles with noble metal cations

A number of 2-(alkynylamino)-substituted heterocycles have been synthesized. These heterocycles rearrange in the presence of silver(I) and gold(I) salts to give novel 2H-pyrimido[2,1-b]benzoxazoles, 2H-pyrimido[2,1-b]benzothiazoles, and a 2H-pyrimido[2,1-b]benzoselenazole. Two of the the 2H-pyrimido[2,1-b]benzoxazoles were isolated in good yield. The kinetics of the silver tetrafluoroborate-catalyzed rearrangements of selected (alkynylamino)benzoxazoles and benzothiazoles have been examined by 1H NMR in CD3CN. Factors affecting the electron densities of the triple bond and of the nitrogen atom in the heterocycle are important in influencing the rate of rearrangement.