57677-79-9

Usage

Uses

Used in Pharmaceutical Research and Development:
2-(4-Methoxy-phenyl)-thiazole-4-carboxylic acid ethyl ester is used as a research compound for exploring its potential therapeutic applications. Its diverse biological activities, such as antibacterial, antifungal, and anticancer properties, make it a valuable asset in the development of new drugs.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-(4-Methoxy-phenyl)-thiazole-4-carboxylic acid ethyl ester is used as a lead compound for the design and synthesis of novel therapeutic agents. Its unique chemical structure and pharmacological properties offer opportunities for the creation of innovative drugs with improved efficacy and safety profiles.
Used in Drug Development:
2-(4-Methoxy-phenyl)-thiazole-4-carboxylic acid ethyl ester is utilized as a candidate for drug development due to its enhanced solubility and bioavailability. Its ethyl ester form allows for better absorption and distribution within the body, increasing the likelihood of successful therapeutic outcomes.
Used in Antimicrobial Agents:
2-(4-Methoxy-phenyl)-thiazole-4-carboxylic acid ethyl ester is used as an antimicrobial agent for its antibacterial and antifungal properties. It can be incorporated into pharmaceutical formulations to combat various microbial infections and contribute to the development of new antibiotics and antifungal drugs.
Used in Anticancer Therapies:
In the context of oncology, 2-(4-Methoxy-phenyl)-thiazole-4-carboxylic acid ethyl ester is used as a potential anticancer agent. Its ability to target and inhibit the growth of cancer cells makes it a promising candidate for the development of novel cancer treatments.
Used in Drug Delivery Systems:
2-(4-Methoxy-phenyl)-thiazole-4-carboxylic acid ethyl ester can be employed in drug delivery systems to improve the bioavailability and therapeutic efficacy of other drugs. Its chemical properties may facilitate the design of innovative drug delivery platforms, such as nanoparticles or liposomes, to enhance the delivery of therapeutic agents to target tissues.

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

• 868-59-7 L-cysteine ethyl ester hydrochloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 41731-52-6 2-chloro-thiazole-4-carboxylic acid ethyl ester 
• 5720-07-0 4-methoxyphenylboronic acid 
• 25984-63-8 4-hydroxythiobenzamide 
• 70-23-5 ethyl Bromopyruvate 
• 3424-93-9 4-methoxyphenylacetamide 
• 100-07-2 4-methoxy-benzoyl chloride 
• 100-09-4 4-methoxybenzoic acid 
• 74-88-4 methyl iodide 
• 874-90-8 4-methoxybenzonitrile 
• 1332708-68-5 C₁₃H₁₅NO₃S 
• 100367-77-9 ethyl 2-bromothiazole-4-carboxylate 
• 3411-58-3 L-cystein ethyl ester 

Downstream Products

• 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 
• 57677-80-2 2-(4-methoxyphenyl)thiazole-4-carboxylic acid 

Relevant academic research and scientific papers

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

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.

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.

INHIBITORS OF HUMAN ATGL

The present invention relates to novel inhibitors of adipose triglyceride lipase (ATGL) having an improved inhibitory activity against human ATGL (hATGL) as well as pharmaceutical compositions comprising these inhibitors, and their therapeutic use, particularly in the treatment or prevention of a lipid metabolism disorder, including, e.g., obesity, non-alcoholic fatty liver disease, type 2 diabetes, insulin resistance, glucose intolerance, hypertriglyceridemia, metabolic syndrome, cardiac and skeletal muscle steatosis, congenital generalized lipodystrophy, familial partial lipodystrophy, acquired lipodystrophy syndrome, atherosclerosis, or heart failure.

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.

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

Powerful Antibacterial Activity of Phenyl-Thiolatobismuth(III) Complexes Derived from Oxadiazolethiones

Seven novel 5-substituted phenylthiazole oxadiazolethiones: [Me-PTOT(H)], [MeO-PTOT(H)], [MeS-PTOT(H)], [F-PTOT(H)], [Cl-PTOT(H)], [Br-PTOT(H)], and [CF3-PTOT(H)], {where X-PTOT(H) = 5-[2-(4-X)thiazol-4-yl]-1,3,4-oxadiazole-2(3H)-thione, 4-X = C6H4}, were synthesised from their corresponding thioamides. From these seven heteroleptic thiolatobismuth complexes: BiPh(Me-PTOT)2 6, BiPh(MeO-PTOT)2 7, BiPh(MeS-PTOT)2 8, BiPh(F-PTOT)2 9, BiPh(Cl-PTOT)2 10, BiPh(Br-PTOT)2 11 and BiPh(CF3-PTOT)2 12 were synthesised and characterised. Complexes [10(DMSO)2] and [11(DMSO)2] were structurally characterised using X-ray diffraction. Evaluation of the antibacterial properties of the thiones and their BiIII complexes against Mycobacterium smegmatis, Staphylococcus aureus (S. aureus), Methicillin-resistant Staphylococcus aureus (MRSA), Vancomycin-resistant Enterococcus (VRE), Enterococcus faecalis (E. faecalis) and Escherichia coli (E. coli) showed that all bismuth(III) complexes were highly effective against all the bacteria, as demonstrated by very low MIC values (1.1-2.1 μM). Complexes BiPh(Me-PTOT)2 6, BiPh(Cl-PTOT)2 10 and BiPh(Br-PTOT)2 11, showed best activity against the multi-drug resistant bacteria VRE and MRSA with an MIC value of 1.0 μM. All these complexes and their corresponding thiones failed to show any prominent activity against M. smegmatis and E. coli, even at high concentrations. These complexes showed little or no toxicity towards mammalian COS-7 cells at 20 μg/mL. Seven heteroleptic thiolatobismuth(III) complexes [BiPh(X-PTOT)2] derived from a series of 5-substituted phenylthiazole oxadiazolethiones [X-PTOT(H)] provide powerful antibacterial action against the multi-resistant bacteria MRSA and VRE.

Copper(II)-catalyzed oxidation of 4-carboxythiazolines and 4-carboxyoxazolines to 4-carboxythiazoles and 4-carboxyoxazoles

A mild copper(II)-catalyzed oxidation of 4-carboxythiazolines and 4-carboxyoxazolines to 4-carboxythiazoles and 4-carboxyoxazoles has been developed. Various substrates with alkyl or aryl substitutions at 2-position on azoline ring could be smoothly oxidi

Oxidation of 4-carboxylate thiazolines to 4-carboxylate thiazoles by molecular oxygen

A facile and environment-benign oxidation by molecular oxygen was applied for the conversion of 4-carboxylate thiazolines to 4-carboxylate thiazoles. The substituent effect on thiazoline ring was investigated. It was found that electron-poor group on the thiazoline ring could facilitate the oxidation.