57677-80-2

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-Methoxyphenyl)-1,3-thiazole-4-carboxylic acid is used as a building block or intermediate in the synthesis of various pharmaceutical compounds for its potential medicinal properties. The presence of the thiazole ring and the carboxylic acid group allows for versatile chemical modifications, making it a valuable component in the development of new drugs with diverse therapeutic effects.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 2-(4-methoxyphenyl)-1,3-thiazole-4-carboxylic acid serves as a key component in the design and synthesis of novel therapeutic agents. Its unique structural features, including the heterocyclic thiazole ring and the methoxyphenyl group, contribute to its potential as a scaffold for creating molecules with specific biological activities, such as antimicrobial, anti-inflammatory, or anticancer properties.

InChI:InChI=1/C11H9NO3S/c1-15-8-4-2-7(3-5-8)10-12-9(6-16-10)11(13)14/h2-6H,1H3,(H,13,14)

Upstream product

• 57677-79-9 ethyl 2-(4-methoxyphenyl)thiazole-4-carboxylate 
• 100-09-4 4-methoxybenzoic acid 
• 100-07-2 4-methoxy-benzoyl chloride 
• 3424-93-9 4-methoxyphenylacetamide 
• 1315510-08-7 methyl 2-(4-methoxylphenyl)thiazole-4-carboxylate 
• 25984-63-8 4-hydroxythiobenzamide 
• 2362-64-3 p-methoxythiobenzamide 

Downstream Products

• 57706-30-6 2-chloro-1-[2-(4-methoxy-phenyl)-thiazol-4-yl]-ethanone 
• 65823-91-8 1-(2-(4-methoxyphenyl)thiazol-4-yl)ethanone 
• 57677-83-5 2-diazo-1-[2-(4-methoxy-phenyl)-thiazol-4-yl]-ethanone 

Relevant academic research and scientific papers

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.

1-(2-(4-methoxyphenyl)thiazolyl-4-yl)ethylamine and synthesis method thereof

The invention belongs to the technical field of organic synthesis, and discloses 1-(2-(4-methoxyphenyl)thiazolyl-4-yl)ethylamine and a chemical synthesis method thereof. The method comprises the following steps: by taking 4-methoxybenzoic acid as a raw material, carrying out acylation, substitution, sulfonylation, substitution, hydrolysis, substitution, substitution and reduction reaction to prepare 1-(2-(4-methoxyphenyl)thiazolyl-4-yl)ethylamine. An efficient synthesis method is provided for synthesis of the compound.

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.

Synthesis, characterization, crystal structure and urease-inhibition activities of three 2-phenylthiazole derivatives

Three 2-phenylthiazole derivatives were synthesized, characterized and evaluated as urease inhibitors. The structures of the 2-phenylthiazole derivatives were characterized by FT-IR, 1H NMR and 13C NMR spectroscopy. Their crystal str

Purple acid phosphatase inhibitors as leads for osteoporosis chemotherapeutics

Purple acid phosphatases (PAPs) are metalloenzymes that catalyse the hydrolysis of phosphate esters under acidic conditions. Their active site contains a Fe(III)Fe(II) metal centre in mammals and a Fe(III)Zn(II) or Fe(III)Mn(II) metal centre in plants. In humans, elevated PAP levels in serum strongly correlate with the progression of osteoporosis and metabolic bone malignancies, which make PAP a target suitable for the development of chemotherapeutics to combat bone ailments. Due to difficulties in obtaining the human enzyme, the corresponding enzymes from red kidney bean and pig have been used previously to develop specific PAP inhibitors. Here, existing lead compounds were further elaborated to create a series of inhibitors with Ki values as low as ～30 μM. The inhibition constants of these compounds were of comparable magnitude for pig and red kidney bean PAPs, indicating that relevant binding interactions are conserved. The crystal structure of red kidney bean PAP in complex with the most potent inhibitor in this series, compound 4f, was solved to 2.40 ? resolution. This inhibitor coordinates directly to the binuclear metal centre in the active site as expected based on its competitive mode of inhibition. Docking simulations predict that this compound binds to human PAP in a similar mode. This study presents the first example of a PAP structure in complex with an inhibitor that is of relevance to the development of anti-osteoporotic chemotherapeutics.