18735-74-5

Basic information

• Product Name: 5-METHYL-2-PHENYL-1,3-OXAZOLE-4-CARBOXYLIC ACID
• Synonyms: 5-METHYL-2-PHENYL-1,3-OXAZOLE-4-CARBOXYLIC ACID;IFLAB-BB F2124-0564;5-Methyl-2-phenyl-1,3-oxazole-4-carboxylic acid 97%;5-Methyl-2-phenyloxazole-4-carboxylic acid;5-Methyl-2-phenyl-oxazol-4-carboxylicacid;4-Oxazolecarboxylic acid, 5-Methyl-2-phenyl-;4-Carboxy-5-methyl-2-phenyl-1,3-oxazole, (4-Carboxy-5-methyl-1,3-oxazol-2-yl)benzene;5-Methyl-2-phenyl-1,3-oxazole-4-carboxylicacid97%
• CAS NO: 18735-74-5
• Molecular Formula: C₁₁H₉NO₃
• Molecular Weight: 203.19
• Product Categories: Heterocycles series;Carboxylic Acids;Oxazoles, Isoxazoles & Benzoxazoles;Carboxylic Acids;Oxazoles, Isoxazoles & Benzoxazoles
• Mol File: 18735-74-5.mol

Chemical Properties

• Melting Point: 182 °C
• Boiling Point: 400.1 °C at 760 mmHg
• Flash Point: 195.8 °C
• Appearance: /
• Density: 1.273 g/cm³
• Vapor Pressure: 4.04E-07mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 3.03±0.32(Predicted)
• CAS DataBase Reference: 5-METHYL-2-PHENYL-1,3-OXAZOLE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYL-2-PHENYL-1,3-OXAZOLE-4-CARBOXYLIC ACID(18735-74-5)
• EPA Substance Registry System: 5-METHYL-2-PHENYL-1,3-OXAZOLE-4-CARBOXYLIC ACID(18735-74-5)

Safety Data

• Hazard Codes: Harmful:
• Hazardous Substances Data: 18735-74-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-METHYL-2-PHENYL-1,3-OXAZOLE-4-CARBOXYLIC ACID is used as a building block for the preparation of oxazole transthyretin amyloidogenesis inhibitors. These inhibitors are designed to prevent the formation of amyloid fibrils, which are associated with various neurodegenerative diseases such as Alzheimer's and transthyretin-related amyloidosis.
Used in Antiviral Drug Development:
In the field of antiviral drug development, 5-METHYL-2-PHENYL-1,3-OXAZOLE-4-CARBOXYLIC ACID is utilized to synthesize inhibitors of HldE kinase. These inhibitors target Gram-negative bacteria, disrupting their virulence factors and potentially leading to the development of novel antivirulence drugs that can combat antibiotic-resistant strains.

InChI:InChI=1/C11H9NO3/c1-7-9(11(13)14)12-10(15-7)8-5-3-2-4-6-8/h2-6H,1H3,(H,13,14)/p-1

Upstream product

• 59171-72-1 2-phenyl-oxazole-4-carboxylic acid methyl ester 
• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 
• 848188-36-3 benzyl 5-methyl-2-phenyloxazole-4-carboxylate 
• 37791-41-6 4-ethylidene-2-phenyl-5-oxazolone 
• 98-88-4 benzoyl chloride 
• 1227492-02-5 (4S,5S)-5-methyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid 
• 18735-67-6 1-(5-methyl-3-oxy-2-phenyl-oxazol-4-yl)-ethanone; hydrochloride 
• 4411-93-2 2-ethylidene-4-oxo-4-phenylbutyric acid 
• 105909-91-9 methyl 2-benzoylamino-3-methylacrylate 
• 61151-90-4 2-benzoylamino-3-oxobutyric acid ethyl ester 
• 99973-53-2 4-(1-chloro-ethylidene)-2-phenyl-4H-oxazol-5-one 
• 495-69-2 Hippuric Acid 
• 77320-41-3 2-benzoylamino-3-oxo-butyric acid methyl ester 

Downstream Products

• 5221-67-0 5-methyl-2-phenyloxazole 
• 51655-71-1 2-phenyl-5-methyl-4-oxazolecarboxylic acid chloride 
• 827-43-0 4-methyl-2-phenyl-1H-imidazole 
• 138676-18-3 5-ethyl-2-phenyloxazole-4-carboxylic acid 
• 1257861-41-8 C₂₇H₃₀N₄O₆ 
• 1257861-40-7 C₁₇H₁₉N₃O₅ 
• 1007123-33-2 ((S)-2,2-dimethyl-1-oxo-1-((S)-2-oxoazepan-3-ylamino)decan-3-yl) 6-(N-(benzyloxy)formamido)-(2S)-2-(5-methyl-2-phenyloxazole-4-carboxamido)hexanoate 
• 52955-65-4 (5-methyl-2-phenyloxazol-4-yl)(phenyl)methanone 
• 57742-59-3 1-(5-methyl-2-phenyl-oxazol-4-yl)-1-phenyl-ethanol 
• 51655-72-2 5-methyl-2-phenyl-oxazole-4-carboxylic acid amide 
• 70170-23-9 5-methyl-2-phenyl-1,3-oxazole-4-carboxaldehyde 

Relevant articles and documents

A mild high yielding synthesis of oxazole-4-carboxylate derivatives

Several 2,5-disubstituted oxazole-4-carboxylates were prepared in high yields from the methyl esters of N-acyl-β-halodehydroaminobutyric acid derivatives by treatment with a 2% solution of DBU in acetonitrile. The scope of this reaction was investigated a

Structure-activity relationship of new anti-tuberculosis agents derived from oxazoline and oxazole benzyl esters

During the syntheses and studies of natural iron chelators (mycobactins), we serendipitously discovered that a simple, small molecule, oxazoline-containing intermediate 3 displayed surprising anti-tuberculosis activity (MIC of 7.7?μM, average). Herein we

Towards Gram-negative antivirulence drugs: New inhibitors of HldE kinase

Gram-negative bacteria lacking heptoses in their lipopolysaccharide (LPS) display attenuated virulence and increased sensitivity to human serum and to some antibiotics. Thus inhibition of bacterial heptose synthesis represents an attractive target for the development of new antibacterial agents. HldE is a bifunctional enzyme involved in the synthesis of bacterial heptoses. Development of a biochemical assay suitable for high-throughput screening allowed the discovery of inhibitors 1 and 2 of HldE kinase. Study of the structure-activity relationship of this series of inhibitors led to highly potent compounds.

Syntheses and biological activity of amamistatin B and analogs

(Chemical Equation Presented) Amamistatins A and B, natural products isolated from a strain of Nocardia, showed growth inhibition against three human tumor cell lines (IC50 0.24-0.56 μM). Structurally related mycobactins affect the growth of bo

Syntheses of amamistatin fragments and determination of their HDAC and antitumor activity

Amamistatins A and B are natural products found to have anti-proliferative effects against MCF-7, A549, and MKN45 human tumor cell lines (IC50 0.24-0.56 μM). It was proposed that their activity was due to histone deacetylase (HDAC) inhibition m

Design, synthesis, and evaluation of oxazole transthyretin amyloidogenesis inhibitors

Ten oxazoles bearing a C(4) carboxyl group were synthesized and evaluated as transthyretin (TTR) amyloid fibril inhibitors. Substituting aryls at the C(2) position of the oxazole ring reveals that a 3,5-dichlorophenyl substituent significantly reduced amy

Solid-phase synthesis of oxazolones and other heterocycles via Wang resin-bound diazocarbonyls

The preparation of Wang resin bound α-diazo-β-ketoesters is described. These highly useful intermediates were used for the synthesis of a series of heterocycle libraries, which were obtained from the resin using TFA cleavage. In addition, a novel route for the synthesis of oxazolones using an N-H insertion strategy is disclosed.

Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis

The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.

Combinatorial synthesis and biological evaluation of library of small-molecule Ser/Thr-protein phosphatase inhibitors

In eukaryotes, phosphorylation of serine, threonine, and tyrosine residues on proteins is a fundamental posttranslational regulatory process for such functions as signal transduction, gene transcription, RNA splicing, cellular adhesion, apoptosis, and cell cycle control. Based on functional groups present in natural product serine/threonine protein phosphatase (PSTPase) inhibitors, we have designed pharmacophore model 1 and demonstrated the feasibility of a combinatorial chemistry approach for the preparation of functional analogues of 1. Preliminary biological testing of 18 structural variants of 1 has identified two compounds with growth inhibitory activity against cultured human breast cancer cells. In vitro inhibition of the PSTPase PP2A was demonstrated with compound Id. Using flow cytometry we observed that compound If caused prominent inhibition in the G1 phase of the cell cycle. Thus, the combinatorial modifications of the minimal pharmacophore 1 can generate biologically interesting antiproliferative agents.