13575-16-1

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 5-phenyloxazole-2-carboxylate is utilized as a key building block in the synthesis of pharmaceutical compounds, particularly for the development of anti-inflammatory and analgesic drugs. Its structural attributes facilitate the creation of novel therapeutic agents that can address various medical conditions.
Used in Agrochemical Industry:
In the agrochemical sector, Ethyl 5-phenyloxazole-2-carboxylate serves as a fundamental component in the production of pesticides. Its integration into these formulations contributes to the development of effective pest control solutions that safeguard crops and enhance agricultural productivity.
Used as a Fluorescent Probe or Chemosensor in Analytical and Biological Studies:
Ethyl 5-phenyloxazole-2-carboxylate is employed as a fluorescent probe or chemosensor, enabling researchers to investigate various biological processes and analyze chemical interactions. Its fluorescent properties allow for the tracking and visualization of specific molecules or cellular events, thereby advancing scientific understanding and discovery in these fields.

InChI:InChI=1/C12H11NO3/c1-2-15-12(14)11-13-8-10(16-11)9-6-4-3-5-7-9/h3-8H,2H2,1H3

Upstream product

• 84978-66-5 ethyl 2-oxo-2-((2-oxo-2-phenylethyl)amino)acetate 
• 5468-37-1 2-aminoacetophenone hydrochloride 
• 4755-77-5 Ethyl oxalyl chloride 
• 2999-46-4 Ethyl isocyanoacetate 
• 98-86-2 acetophenone 
• 623-33-6 glycine ethyl ester hydrochloride 
• 4636-16-2 iodoacetophenone 
• 1075-06-5 2,2-dihydroxy-1-phenyl-ethanone 
• 98-88-4 benzoyl chloride 
• 7063-99-2 ethyl 5-phenylisoxazole-3-carboxylate 
• 1499-53-2 ethyl hippurate 
• 613-89-8 2-Aminoacetophenone 
• 541-41-3 chloroformic acid ethyl ester 
• 108665-44-7 5-phenyl-2-(trimethylsilyl)oxazole 

Downstream Products

• 1014-14-8 5-phenyl-1,3-oxazole-2-carboxylic acid 
• 84978-61-0 5-phenyl-2-oxazolecarbonylhydrazine 
• 90770-99-3 5-phenyl-oxazole-2-carboxylic acid amide 
• 90831-39-3 N-methyl-5-phenyl-2-oxazolecarboxamide 
• 70594-46-6 5-phenyl-oxazole-2-carbonitrile 
• 93689-70-4 5-phenyl-oxazole-2-carbothioic acid amide 
• 70594-50-2 5-(4-nitro-phenyl)-oxazole-2-carbonitrile 
• 90868-63-6 5-(4-nitro-phenyl)-oxazole-2-carboxylic acid amide 
• 94487-79-3 5-(4-amino-phenyl)-oxazole-2-carbothioic acid amide 
• 95195-72-5 5-(4-acetylamino-phenyl)-oxazole-2-carbothioic acid amide 
• 161291-35-6 N-hydroxy-5-phenyloxazole-2-carboxamide 

Relevant academic research and scientific papers

Highly hydrophilic 1,3-oxazol-5-yl benzenesulfonamide inhibitors of carbonic anhydrase II for reduction of glaucoma-related intraocular pressure

Four inhibitors of human carbonic anhydrase II (hCA II) were designed based on the previously reported subnanomolar 1,3-oxazole-based sulfonamide inhibitors of the enzyme to incorporate primary and secondary amine functionality in the carboxamide side cha

BENZENESULFONAMIDE DERIVATIVES AS TRAP1 MODULATORS AND USES THEREOF

The present disclosure provides compounds of Formula (I): and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled compounds, and prodrugs thereof. The provided compounds may be tumor necrosis factor ("TNF") receptor associated protein 1 ("TRAP1") modulators (e.g., TRAP1 activators). The provided compounds may also rescue the activity in PTEN-induced kinase 1 ("PINK1") loss of function contexts. The provided compounds may also improve mitochondrial health, function, quality, quantity, and/or activity, and/or reduce the production of reactive oxygen species. The provided compounds may also refold or solubilize aggregated or misfolded proteins such as α-synuclein. The present disclosure also provides pharmaceutical compositions comprising the provided compounds; kits comprising the provided compounds or pharmaceutical compositions; and methods of using the provided compounds and pharmaceutical compositions (e.g., for treating a disease in a subject in need thereof).

PYRIDINESULFONAMIDE DERIVATIVES AS TRAP1 MODULATORS AND USES THEREOF

The present disclosure provides compounds of Formula (I): and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled compounds, and prodrugs thereof. The provided compounds may be tumor necrosis factor ("TNF") receptor associated protein 1 ("TRAP1") modulators (e.g., TRAP1 activators). The provided compounds may also rescue the activity in PTEN-induced kinase 1 ("PINK1") loss of function contexts. The provided compounds may also improve mitochondrial health, function, quality, quantity, and/or activity, and/or reduce the production of reactive oxygen species. The provided compounds may also refold or solubilize aggregated or misfolded proteins such as a-synuclein. The present disclosure also provides pharmaceutical compositions comprising the provided compounds; kits comprising the provided compounds or pharmaceutical compositions; and methods of using the provided compounds and pharmaceutical compositions (e.g., for treating a disease in a subject in need thereof).

Development of a continuous flow photoisomerization reaction converting isoxazoles into diverse oxazole products

A continuous flow process is presented, which directly converts isoxazoles into their oxazole counterparts via a photochemical transposition reaction. This results in the first reported exploitation of this transformation to establish its scope and synthe

Silver-Induced [3+2] Cycloaddition of Isocyanides with Acyl Chlorides: Regioselective Synthesis of 2,5-Disubstituted Oxazoles

A silver-induced cycloaddition of isocyanides with acyl chlorides has been developed. This transition metal-catalyzed strategy provides an effective and scalable approach for the formation of 2,5-disubstituted oxazoles in good to high yields. The employed silver-based MOF catalyst can be efficiently recycled without compromising the yield.

Discovery of Novel Aryl Carboxamide Derivatives as Hypoxia-Inducible Factor 1α Signaling Inhibitors with Potent Activities of Anticancer Metastasis

In order to discover novel hypoxia-inducible factor 1 (HIF-1) inhibitors for the cancer metastasis treatment, 68 new aryl carboxamide compounds were synthesized and evaluated for their inhibitory effect by dual luciferase-reporter assay. Based on five rounds of investigation on structure-activity relationships step by step, compound 30m was discovered as the most active inhibitor (IC50 = 0.32 μM) with no obvious cytotoxicity (CC50 > 50 μM). It effectively attenuated hypoxia-induced HIF-1α protein accumulation and reduced transcription of vascular epidermal growth factor in a dose-dependent manner, which was further demonstrated by its inhibitory potency on capillary-like tube formation, angiogenesis of zebrafish as well as cellular migration and invasion. Importantly, compound 30m exhibited antimetastatic potency in breast cancer lung metastasis in the mice model, indicating its promising therapeutic potential for prevention and treatment of tumor metastasis. These results definitely merit attention for further rational design of more efficient HIF-1 inhibitors in the future.

Novel Compounds

The present invention relates to novel compounds and methods for the manufacture of inhibitors of deubiquitylating enzymes (DUBs). In particular, the invention relates to the inhibition of ubiquitin C- terminal hydrolase 30 or Ubiquitin Specific Peptidase 30 (USP30). The invention further relates to the use of DUB inhibitors in the treatment of conditions involving mitochondrial dysfunction and cancer. Compounds of the invention include compounds having the formula (I): (I) or a pharmaceutically acceptable salt thereof, wherein R1a, R1b, R1c, R1d, R1e, R1f, R1g, R2, X, L and A are as defined herein.

I2-Promoted formal [3+2] cycloaddition of α-methylenyl isocyanides with methyl ketones: a route to 2,5-disubstituted oxazoles

An I2-promoted formal [3+2] cycloaddition for access to oxazoles has been demonstrated. This is the first example of a Lewis acid-promoted formal [3+2] cycloaddition of isocyanides with methyl ketones involving the C≡N cleavage of isocyanides. The salient feature of this approach is unconventional 2,5-disubstituted oxazole formation from isocyanides and ketones rather than 4,5-substituted oxazoline.

IAP BIR domain binding compounds

A compound of Formula 1: (I) or salt thereof, as well as methods of making compounds of Formula 1, methods of using compounds of Formula 1 to treat proliferative disorders such as cancer, and related compounds, composition, and methods.

Probing the 'bipolar' nature of the carbonic anhydrase active site: Aromatic sulfonamides containing 1,3-oxazol-5-yl moiety as picomolar inhibitors of cytosolic CA I and CA II isoforms

Abstract A series of potent inhibitors of human carbonic anhydrase (CA) isoforms I and II has been prepared via a direct, chemoselective sulfochlorination of a range of 1,3-oxazolyl benzenes and thiophenes, followed by primary sulfonamide synthesis. The latter functionality is a known zinc-binding group (ZBG) responsible for anchoring the inhibitors to the CA's zinc metal ion. The compound's periphery as well as the overall scaffold geometry was designed to enable optimal interactions with the two distinct sides of the enzyme's active site, one of which is lined with hydrophobic residues and while the other is predominantly hydrophilic. As a result, several compounds inhibiting the therapeutically important cytosolic CA I and CA II in picomolar range have been identified. These compounds are one of the most potent CA inhibitors identified to-date. Not only the remarkable (>10 000-fold), cytosolic CA I and CA II selectivity vs. the membrane-bound CA IX and CA XII isoforms, but also the pronounced CA II/I selectivity observed in some cases, allow considering this series as a set of isoform-selective chemical biology tools and promising starting points for drug candidate development.