33763-20-1

Usage

Uses

Used in Chemical Synthesis:
4-METHYL-2-PHENYL-1,3-THIAZOLE-5-CARBOXYLIC ACID is used as a reagent in the Pd-catalyzed decarboxylative C-H cross-coupling of oxazoles and thiazoles. This application takes advantage of the compound's ability to participate in cross-coupling reactions, which are essential in the synthesis of various complex organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.
In the field of organic chemistry, 4-METHYL-2-PHENYL-1,3-THIAZOLE-5-CARBOXYLIC ACID serves as a valuable building block for the creation of novel molecules with potential applications in various industries. Its unique structure and reactivity make it a promising candidate for the development of new chemical entities with specific properties and functions.

InChI:InChI=1/C11H9NO2S/c1-7-9(11(13)14)15-10(12-7)8-5-3-2-4-6-8/h2-6H,1H3,(H,13,14)/p-1

Upstream product

• 2227-79-4 benzenecarbothioamide 
• 609-15-4 ethyl 2-chloro-3-oxo-butyrate 
• 7520-94-7 5-acetyl-4-methyl-2-phenylthiazole 
• 80269-16-5 2-Phenyl-4-methyl-5-glyoxyloyl-thiazol 
• 54001-18-2 4-methyl-2-phenyl-thiazole-5-carbonyl chloride 
• 55-21-0 benzamide 
• 80269-25-6 2-Phenyl-4-methyl-thiazol-5-yl-glykolsaeure 
• 53715-64-3 4-methyl-2-phenyl-thiazole-5-carboxylic acid ethyl ester 

Downstream Products

• 1826-17-1 4-methyl-2-phenyl-thiazole 
• 113366-60-2 4-(3-hydroxypentyl)-2-phenylthiazole-5-carboxylic acid 
• 113366-58-8 4-(but-3-enyl)-2-phenylthiazole-5-carboxylic acid 
• 113366-59-9 4-(2-hydroxy-2-phenylpropyl)-2-phenylthiazole-5-carboxylic acid 
• 113366-57-7 4-ethyl-2-phenylthiazole-5-carboxylic acid 
• 54347-80-7 2-chloro-1-(4-methyl-2-phenyl-thiazol-5-yl)-ethanone 
• 54001-08-0 1-[4-methyl-2-(4-nitro-phenyl)-thiazol-5-yl]-ethanone 
• 54000-90-7 2-chloro-1-[4-methyl-2-(4-nitro-phenyl)-thiazol-5-yl]-ethanone 
• 7520-94-7 5-acetyl-4-methyl-2-phenylthiazole 
• 7520-95-8 2-bromo-1-(4-methyl-2-phenyl-1,3-thiazol-5-yl)-1-ethanone 
• 15911-28-1 2-diazo-1-[4-methyl-2-(4-nitro-phenyl)-thiazol-5-yl]-ethanone 
• 16059-29-3 4-methyl-2-(4-nitro-phenyl)-thiazole-5-carbonyl chloride 
• 54001-24-0 2-diazo-1-(4-methyl-2-phenyl-thiazol-5-yl)-ethanone 
• 478371-38-9 5-[4-methoxy-3-({[(4-methyl-2-phenyl-1,3-thiazol-5-yl)carbonyl]amino}methyl)phenyl]-2-floic acid 

Relevant academic research and scientific papers

Thiazole hydrazide compound as well as preparation method and application thereof

The invention relates to a thiazole hydrazide compound as well as a preparation method and application thereof. The compound has the structure shown by the general formula (I). The compound has a good inhibition effect on pathogenic fungi and bacteria, an

Thiazole amide derivative and application thereof in antitumor drugs

The invention belongs to the technical field of medicines, and provides a thiazole amide derivative shown as a general formula and a preparation method thereof. The invention further discloses use ofthe thiazole amide derivative as a wnt inhibitor, and the thiazole amide derivative has obvious antitumor activity.

Structure-activity relationships of thiazole and benzothiazole derivatives as selective cannabinoid CB2 agonists with in vivo anti-inflammatory properties

The strong therapeutic potential of CB2 receptor agonists for use as anti-inflammatory agents that lack psychiatric side effects has attracted substantial interest. We herein describe the rational design and synthesis of novel thiazole and benzothiazole derivatives and the evaluation of their binding affinity and functional activity on CB1 and CB2 receptors. The series with the general formula N-(3-pentylbenzo [d]thiazol-2(3H)-ylidene) carboxamide (compounds 6a-6d) exhibited the highest affinity and selectivity towards CB2 receptors with Kis in the picomolar or low nanomolar range, and selectivity indices (Ki hCB1/Ki hCB2) reaching up to 429 fold. Notably, these compounds also demonstrated an agonistic functional activity in cellular assays with EC50s in the low nanomolar range. More interestingly, compound 6d, the 3-(trifluoromethyl)benzamide derivative, exhibited remarkable protection against DSS-induced acute colitis in mice model.

Discovery of 2-phenylthiazole-4-carboxylic acid, a novel and potent scaffold as xanthine oxidase inhibitors

The xanthine oxidase (XO) plays an important role in producing uric acid, and therefore XO inhibitors are considered as one of the promising therapies for hyperuricemia and gout. We have previously reported a series of XO inhibitors with pyrazole scaffold to extend the chemical space of current XO inhibitors. Herein, we describe further structural optimization to explore the optimal heterocycle by replacing the thiazole ring of Febuxostat with 5 heterocycle scaffolds unexplored in this field. All of these efforts resulted in the identification of compound 8, a potent XO inhibitor (IC50 = 48.6 nM) with novel 2-phenylthiazole-4-carboxylic acid scaffold. Moreover, lead compound 8 exhibited hypouricemic effect in potassium oxonate-hypoxanthine-induced hyperuricemic mice. These results promote the understanding of ligand-receptor interaction and might help to design more promising XO inhibitors.

Design, synthesis and evaluation of aromatic heterocyclic derivatives as potent antifungal agents

To further enhance the anti-Aspergillus efficacy of our previously discovered antifungal lead compounds (1), a series of aromatic heterocyclic derivatives were designed, synthesized and evaluated for in vitro antifungal activity. Many of the target compounds showed good inhibitory activity against Candida albicans and Cryptococcus neoformans. In particular, the isoxazole nuclei were more suited for improving the activity against Aspergillus spp. Among these compounds, 2-F substituted analogues 23g and 23h displayed the most remarkable in vitro activity against Candida spp., C. neoformans, A. fumigatus and fluconazole-resistant C.alb. strains, which is superior or comparable to the activity of the reference drugs fluconazole and voriconazole. Notably, the compounds 23g and 23h exhibited low inhibition profiles for various isoforms of human cytochrome P450 and excellent blood plasma stability.

Identification, synthesis and photo-protection evaluation of arylthiazole derivatives as a novel series of sunscreens

A novel series of arylthiazole derivatives have been designed, synthesized and evaluated in preventing keratinocytes cell (HaCaT) from UVB exposure induced cellar damage. The structure-activity relationship (SAR) was discussed. More importantly, compound 5a significantly protected the dorsal skin of BALB/c-nu mice against UVB-induced decrustation in vivo. The in vitro and in vivo data for these arylthiazole derivatives suggest further studies for their potential use as photo-protection agents as well as sunscreen candidates.

The effect of some 4,2 and 5,2 bisthiazole derivatives on nitro-oxidative stress and phagocytosis in acute experimental inflammation

Nineteen bisthiazoles were tested in order to assess their anti-inflammatory and antioxidant properties. First, we evaluated the in vitro direct antioxidant capacity of the bisthiazoles using the DPPH radical scavenging method. Then, the anti-inflammatory

ACYLSULFONAMIDES AND PROCESSES FOR PRODUCING THE SAME

The present disclosure relates to acylsulfonamides and processes for their preparation. The processes involve a target-guided synthesis approach, whereby a thioacid and a sulfonyl azide are reacted in the presence of a biological target protein, a Bcl-2 family protein, to form the acylsulfonamide.

Bcl-XL-templated assembly of its own protein-protein interaction modulator from fragments decorated with thio acids and sulfonyl azides

Protein-protein interactions have key importance in various biological processes and modulation of particular protein-protein interactions has been shown to have therapeutic effects. However, disrupting or modulating protein-protein interactions with low-molecular-weight compounds is extremely difficult due to the lack of deep binding pockets on protein surfaces. Herein we describe the development of an unprecedented lead synthesis and discovery method that generates only biologically active compounds from a library of reactive fragments. Using the protein Bcl-XL, a central regulator of programmed cell death, we demonstrated that an amidation reaction between thio acids and sulfonyl azides is applicable for Bcl-XL-templated assembly of inhibitory compounds. We have demonstrated for the first time that kinetic target-guided synthesis can be applied not only on enzymatic targets but also for the discovery of small molecules modulating protein-protein interactions. Copyright

Substituted 2-[(4-aminomethyl)phenoxy]-2-methylpropionic acid PPARα agonists. 1. Discovery of a novel series of potent HDLc raising agents

The peroxisome proliferator activated receptors PPARα, PPARγ, and PPARδ are ligand-activated transcription factors that play a key role in lipid homeostasis. The fibrates raise circulating levels of high-density lipoprotein cholesterol and lower levels of triglycerides in part through their activity as PPARα agonists; however, the low potency and restricted selectivity of the fibrates may limit their efficacy, and it would be desirable to develop more potent and selective PPARα agonists. Modification of the selective PPARδ agonist 1 (GW501516) so as to incorporate the 2-aryl-2-methylpropionic acid group of the fibrates led to a marked shift in potency and selectivity toward PPARα agonism. Optimization of the series gave 25a, which shows EC50 = 4 nM on PPARα and at least 500-fold selectivity versus PPARγ and PPARγ. Compound 25a (GW590735) has been progressed to clinical trials for the treatment of diseases of lipid imbalance.