57677-79-9

Basic information

• Product Name: 2-(4-METHOXY-PHENYL)-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: 2-(4-METHOXY-PHENYL)-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER;ETHYL 2-(4-METHOXYPHENYL)-1,3-THIAZOLE-4-CARBOXYLATE;Ethyl 2-(4-methoxyphenyl)thiazole-4-carboxylate;4-Thiazolecarboxylic acid, 2-(4-methoxyphenyl)-, ethyl ester
• CAS NO: 57677-79-9
• Molecular Formula: C₁₃H₁₃NO₃S
• Molecular Weight: 263.31
• EINECS: 604-604-1
• Mol File: 57677-79-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 94-96°C
• Boiling Point: 399.783°C at 760 mmHg
• Flash Point: 195.582°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.566
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-(4-METHOXY-PHENYL)-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-METHOXY-PHENYL)-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER(57677-79-9)
• EPA Substance Registry System: 2-(4-METHOXY-PHENYL)-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER(57677-79-9)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 57677-79-9(Hazardous Substances Data)

Usage

General Description

2-(4-Methoxy-phenyl)-thiazole-4-carboxylic acid ethyl ester is a chemical compound with the molecular formula C13H13NO3S. It belongs to the thiazole carboxylic acid ester group and contains a thiazole ring and a methoxyphenyl group. It is commonly used in pharmaceutical research and development due to its potential pharmacological properties. 2-(4-METHOXY-PHENYL)-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER is of interest in medicinal chemistry as it exhibits various biological activities, including antibacterial, antifungal, and anticancer properties. Its ethyl ester form allows for better solubility and bioavailability, making it a promising candidate for drug development. Overall, 2-(4-Methoxy-phenyl)-thiazole-4-carboxylic acid ethyl ester is a valuable chemical with potential therapeutic applications.

InChI:InChI=1/C13H13NO3S/c1-3-17-13(15)11-8-18-12(14-11)9-4-6-10(16-2)7-5-9/h4-8H,3H2,1-2H3

Upstream product

• 25984-63-8 4-hydroxythiobenzamide 
• 70-23-5 ethyl Bromopyruvate 
• 41731-52-6 2-chloro-thiazole-4-carboxylic acid ethyl ester 
• 5720-07-0 4-methoxyphenylboronic acid 
• 3424-93-9 4-methoxyphenylacetamide 
• 100-07-2 4-methoxy-benzoyl chloride 
• 100-09-4 4-methoxybenzoic acid 
• 868-59-7 L-cysteine ethyl ester hydrochloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 74-88-4 methyl iodide 
• 874-90-8 4-methoxybenzonitrile 
• 1332708-68-5 C₁₃H₁₅NO₃S 
• 60297-48-5 C₁₃H₁₅NO₃S 
• 100367-77-9 ethyl 2-bromothiazole-4-carboxylate 

Downstream Products

• 57677-80-2 2-(4-methoxyphenyl)thiazole-4-carboxylic acid 
• 1023594-48-0 2-(4-methoxy-phenyl)-thiazole-4-carboxylic acid hydrochloride 
• 885279-75-4 2-(4-methoxyphenyl)-4-hydroxymethylthiazole 
• 57677-83-5 2-diazo-1-[2-(4-methoxy-phenyl)-thiazol-4-yl]-ethanone 
• 57706-30-6 2-chloro-1-[2-(4-methoxy-phenyl)-thiazol-4-yl]-ethanone 

Relevant articles and documents

Synthesis, crystal structure and biological evaluation of novel 2-phenylthiazole derivatives as butyrylcholinesterase inhibitors

To find novel butyrylcholinesterase inhibitors, three novel 2-phenylthiazole derivatives were synthesised. The synthesised compounds were characterised by NMR and single-crystal X-ray diffraction analysis. Hirshfeld surface analysis and two-dimensional fingerprint plots of the compounds were used as a theoretical approach to assess the driving force for crystal structure formation via the intermolecular interactions in the crystal lattices of the synthesised compounds. Among the three compounds, N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro- 1H-pyrazol-4-yl)-2-(4-methoxyphenyl)thiazole-4-carboxamide showed the best butyrylcholinesterase-inhibition activity with an IC50 value of 75.12 μM. A docking study demonstrated that this compound interacts with the peripheral anionic site of butyrylcholinesterase.

Design, synthesis and biological evaluation of novel thiazole-derivatives as mitochondrial targeting inhibitors of cancer cells

Mitochondria are pivotal energy production sources for cells to maintain necessary metabolism activities. Targeting dysfunctional mitochondrial features has been a hotspot for mitochondrial-related disease researches. Investigation with cancerous mitochondrial metabolism is a continuing concern within tumor therapy. Herein, we set out to assess the anti-cancer activities of a novel family of TPP-thiazole derivatives based on our earlier research on mitochondrial targeting agents. Specifically, we designed and synthesized a series of TPP-thiazole derivatives and revealed by the MTT assay that most synthesized compounds effectively inhibited three cancer cell lines (HeLa, PC3 and MCF-7). After structure modifications, we explored the SAR relationships and identified the most promising compound R13 (IC50 of 5.52 μM) for further investigation. In the meantime, we performed ATP production assay to assess the selected compounds inhibitory effect on HeLa cells energy production. The results displayed the test compounds significantly restrained ATP production of cancer cells. Overall, we have designed and synthesized a series of compounds which exhibited significant cytotoxicity against cancer cells and effectively inhibited mitochondrial energy production.

Identification of BR102910 as a selective fibroblast activation protein (FAP) inhibitor

Fibroblast activation protein (FAP) belongs to the family of prolyl-specific serine proteases and displays both exopeptidase and endopeptidase activities. FAP expression is undetectable in most normal adult tissues, but is greatly upregulated in sites of tissue remodeling, which include fibrosis, inflammation and cancer. Due to its restricted expression pattern and dual enzymatic activities, FAP inhibition is investigated as a therapeutic option for several diseases. In the present study, we described the structure–activity relationship of several synthesized compounds against DPPIV and prolyl oligopeptidase (PREP). In particular, BR102910 (compound 24) showed nanomolar potency and high selectivity. Moreover, the in vivo FAP inhibition study of BR102910 (compound 24) using C57BL/6J mice demonstrated exceptional profiles and satisfactory FAP inhibition efficacy. Based on excellent in vitro and in vivo profiles, the potential of BR102910 (compound 24) as a lead candidate for the treatment of type 2 diabetes is considered.

I2/TBHP-Mediated tandem cyclization and oxidation reaction: Facile access to 2-substituted thiazoles and benzothiazoles

The efficient synthesis of 2-substituted thiazoles and benzothiazoles has been accomplished employing readily available cysteine esters and 2-aminobenzenethiols as N and S sources. The reaction proceeds under an I2/TBHP system and involves a on