83558-09-2

Usage

Uses

Used in Organic Synthesis:
2-CHLORO-N-[4-(4-FLUORO-PHENYL)-THIAZOL-2-YL]-ACETAMIDE is used as a building block in organic synthesis for the creation of more complex molecules. Its unique structure allows for the formation of various chemical bonds and reactions, making it a valuable component in the synthesis of new compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-CHLORO-N-[4-(4-FLUORO-PHENYL)-THIAZOL-2-YL]-ACETAMIDE is used as a lead compound for the development of new drugs. Its molecular structure suggests that it may possess biological and pharmacological activities, which can be further explored through laboratory testing and research. 2-CHLORO-N-[4-(4-FLUORO-PHENYL)-THIAZOL-2-YL]-ACETAMIDE has the potential to be optimized and modified to target specific diseases or conditions, contributing to the advancement of medicinal chemistry.
Used in Medicinal Chemistry:
2-CHLORO-N-[4-(4-FLUORO-PHENYL)-THIAZOL-2-YL]-ACETAMIDE is utilized in medicinal chemistry for the study of its potential therapeutic properties. Its unique molecular structure allows researchers to investigate its interactions with biological targets, such as enzymes, receptors, or other proteins, which may lead to the discovery of new drug candidates with improved efficacy and selectivity.

InChI:InChI=1/C11H8ClFN2OS/c12-5-10(16)15-11-14-9(6-17-11)7-1-3-8(13)4-2-7/h1-4,6H,5H2,(H,14,15,16)

Upstream product

• 403-29-2 2-bromo-4'-fluoroacetophenone 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 79-04-9 chloroacetyl chloride 
• 77815-14-6 2-amino-4-(4-fluorophenyl)thiazole 

Downstream Products

• 83558-11-6 2-piperidinoacetamido-4-p-fluorophenylthiazole 
• 83558-16-1 2-(N,N-di-n-butylaminoacetamido)-4-p-fluorophenylthiazole 
• 1048643-70-4 N-[4-(4-fluorophenyl)thiazol-2-yl]-2-[{[4-(4-fluorophenyl)thiazol-2-ylcarbamoyl]-methyl}-(2-methoxybenzyl)amino]acetamide 
• 1048643-67-9 N-[4-(4-fluorophenyl)thiazol-2-yl]-2-[(tetrahydrofuran-2-ylmethyl)amino]acetamide 
• 1048643-64-6 2-(2-acetylaminophenoxy)-N-[4-(4-fluorophenyl)thiazol-2-yl]acetamide 
• 1048643-65-7 2-[2-(2-fluoro-phenyl)ethylamino]-N-[4-(4-fluorophenyl)thiazol-2-yl]acetamide 
• 570363-24-5 2-(2-aminophenylsulfanyl)-N-[4-(4-fluorophenyl)thiazol-2-yl]acetamide 
• 1048643-63-5 N-[4-(4-fluorophenyl)thiazol-2-yl]-2-(2-mercaptophenylamino)acetamide 
• 1048643-66-8 2-[2-(4-fluorophenoxy)ethylamino]-N-[4-(4-fluorophenyl)thiazol-2-yl]acetamide 
• 1048643-69-1 N-[4-(4-fluorophenyl)thiazol-2-yl]-2-(2-hydroxyphenylsulfanyl)acetamide 
• 904769-75-1 2-((2-((4-(4-fluorophenyl)thiazol-2-yl)amino)-2-oxoethyl)thio)acetic acid 
• 83558-18-3 2-(N,N-dibenzylaminoacetamido)-4-p-fluorophenylthiazole 
• 83558-13-8 2-(N,N-diethylaminoacetamido)-4-p-fluorophenylthiazole 
• 83558-14-9 2-(N,N-di-n-propylaminoacetamido)-4-p-fluorophenylthiazole 

Relevant academic research and scientific papers

Design and synthesis of phenoxymethybenzoimidazole incorporating different aryl thiazole-triazole acetamide derivatives as α-glycosidase inhibitors

A novel series of phenoxymethybenzoimidazole derivatives (9a-n) were rationally designed, synthesized, and evaluated for their α-glycosidase inhibitory activity. All tested compounds displayed promising α-glycosidase inhibitory potential with IC50 values in the range of 6.31 to 49.89?μM compared to standard drug acarbose (IC50 = 750.0 ± 10.0?μM). Enzyme kinetic studies on 9c, 9g, and 9m as the most potent compounds revealed that these compounds were uncompetitive inhibitors into α-glycosidase. Docking studies confirmed the important role of benzoimidazole and triazole rings of the synthesized compounds to fit properly into the α-glycosidase active site. This study showed that this scaffold can be considered as a highly potent α-glycosidase inhibitor.

Synthesis and biological screening of diethyl [N-(thiazol-2-yl)carbamoyl]methylphosphonates

A three-step synthesis, involving condensation of bromomethyl aryl ketones with urea to afford 2- aminothiazoles, their chloroacetylation and subsequent solvent-free Arbuzov phosphonation has afforded a series of novel diethyl [N-(thiazol-2-yl)carbamoyl]methylphosphonates 3a-3f in good overall yields; the 4- carboxythiazole analogue 3g was obtained by selective hydrolysis of the corresponding ethyl ester 3f. The phosphonate esters exhibited significant anti-cancer activity (nM - low μM IC50 values) against SH-SY5Y cells and, in one case, 7.6 μM MIC90 anti-TB activity against the virulent M. tuberculosis H37Rv strain; the chloroacetamido precursors all exhibited some antimalarial (PfLDH) activity, three with IC50 values in the range 1.0 - 8.9 μM.

Synthesis, biological evaluation, and docking studies of novel 5,6-diaryl-1,2,4-triazine thiazole derivatives as a new class of α-glucosidase inhibitors

A novel 5,6-diaryl-1,2,4-triazine thiazole derivatives (7a-7q) were synthesized and characterized by 1H NMR and 13C NMR and evaluated for their α-glucosidase inhibitory activity. All tested compounds displayed good α-glucosidase inhibitory activity with IC50 values ranging between 2.85 ± 0.13 and 14.19 ± 0.23 μM when compared to the standard drug acarbose (IC50 = 817.38 ± 6.27 μM). Compound 7i (IC50 = 2.85 ± 0.13 μM) exhibited the highest activity among this series of compounds. Molecular docking studies were carried out in order to investigate the binding mode of this class of compounds to α-glucosidase. This study showed that these 5,6-diaryl-1,2,4-triazine thiazole derivatives are a new class of α-glucosidase inhibitors.

Synthesis, antibacterial, antifungal, and antioxidant evaluation of some new thiazole clubbed oxadiazole derivatives

A series of thiazole incorporated oxadiazole derivatives (6a-6f) was synthesized by reacting 2-chloro-N-(4-(4-substituted phenyl) thiazol-2-yl) acetamide with 5-pyridine-1,3,4-oxadiazole-2-thione using multistep solution phase chemistry. The synthesized compounds were structurally characterized on the basis of elemental analysis and using various spectral data. All the compounds were evaluated for their in vitro antibacterial, antifungal, and antioxidant activity. Some of the new compounds exhibited good antimicrobial and antioxidant activity and are suitable candidates for further scientific explorations.

Design and discovery of novel thiazole derivatives as potential MMP inhibitors to protect against acute lung injury in sepsis rats: Via attenuation of inflammation and apoptotic oxidative stress

Acute lung injury (ALI) is considered to be an inflammatory syndrome of the airway system that is initiated by failure of the respiratory system. In this study, we evaluated the possible benefits of some novel thiazole derivatives against ALI. These derivatives were synthesised and evaluated for the inhibition of MMP-8 and MMP-2. Most of the tested compounds had better inhibitory activity for MMP-8 than for MMP-2, with compound 26 being the most potent analogue among the tested series. Thus, compound 26 was further investigated to determine its beneficial effects in an ALI model of rats with sepsis. In vivo results suggested that compound 26 significantly reduced the protein concentration together with a decline in enhanced leukocytes compared with those in ALI induced by cecal ligation and puncture. The effect of compound 26 on myeloperoxidase activity was also quantified, which was found to be significantly reduced at the maximum tested dose of 20 mg kg-1. The protective effect of compound 26 against ALI was also established to occur via the significant modulation of various biomarkers; for example, the malondialdehyde level was found to be reduced, while there were increased levels of superoxide dismutase and glutathione. Thus, it is proposed that compound 26 exerts a protective effect against ALI via modulation of the antioxidant status. Furthermore, the compounds tested caused significant attenuation of the levels of tumour necrosis factor-α, interleukin-1β, and interleukin-6, and protected the lung through the modulation of systemic inflammatory mediators in septic rats. In conclusion, we identified a novel series of thiazoles, which potentially exert protective effects against ALI via the inhibition of numerous pathways.

Design and Synthesis of 3-Substituted-thiazolyl-2-iminothiazolidin-4-ones as a New Class of Anticonvulsants

A new series of 3-substituted-thiazolyl-2-iminothiazolidin-4-ones were synthesized by nucleophilic substitution of p-substituted-thiazol-2-yl-chloroacetamides with potassium thiocyanide by cyclization. The starting material p-substituted-thiazol-2-yl-chloroacetamides were synthesized from p-substituted-thiazol-2-yl-amines with chloroacetyl chloride, which in turn was prepared from one pot reaction of substituted aryl acetophenone and amino group of thiourea. The title compounds were investigated for their anticonvulsant activity. Among the tested compounds, compound 3-(4-(4-fluorophenyl)thiazol-2-yl)-2-iminothiazolidin-4-one (16) emerged as the most active compound of the series, and it is moderately more potent than the reference standard diazepam.

Design, synthesis and biological evaluation of thiazole- and indole-based derivatives for the treatment of type II diabetes

Present studies have shown that the lipid carrier has a significant role in several aspects of metabolic syndrome in A-FABP/ap2-deficient mice, including type 2 diabetes and atherosclerosis. 38 Thiazole- and indole-based derivatives were synthesized and investigated for their inhibitory effects on the production of LPS-stimulated TNF-α. Among them, 12b exhibited an excellent inhibitory efficiency compared to BMS309403 (95% vs. 85%) at the concentration of 10 μM and a binding affinity for ap2 with the apparent Ki values 33 nM. Oral administration of 12b at a dosage of 50 mg/kg effectively reduced the levels of plasma blood glucose, triglycerides, insulin, total cholesterol and alanine aminotransferase in high-fat/diet-induced obesity model. The results highlighted that 12b was a potent anti-diabetic agent.

METHODS OF USING THIAZOLE, OXAZOLE AND IMIDAZOLE COMPOUNDS IN TREATING SODIUM CHANNEL-MEDIATED DISEASES OR CONDITIONS

This invention is directed to methods of using thiazole, oxazole and imidazole compounds of formula (I): wherein A is -S-, -O- or N(R5), and R1, R2, R3 and R5 are as defined herein, as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a pharmaceutically acceptable salt, solvate or prodrug thereof, for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain.