38205-60-6

Usage

Uses

Used in Flavor and Fragrance Industry:
5-Acetyl-2,4-dimethylthiazole is used as a flavoring agent for its nutty, roasted, meaty, and savory taste characteristics, along with woody and coffee nuances. It is particularly effective at low concentrations (10 ppm), where it can significantly enhance the overall flavor profile of various food products.
Used in Chemical Synthesis:
5-Acetyl-2,4-dimethylthiazole can be utilized as a building block or intermediate in the synthesis of more complex organic compounds, particularly those with potential applications in the pharmaceutical, agrochemical, or materials science industries. Its unique chemical structure and properties make it a valuable component in the development of novel molecules with specific functionalities.
Used in Analytical Chemistry:
Due to its distinct odor and chemical properties, 5-Acetyl-2,4-dimethylthiazole can be employed as a reference compound or standard in the field of analytical chemistry. It can be used to calibrate instruments designed to detect and analyze volatile organic compounds, as well as to train professionals in the identification and recognition of specific chemical odors.
Used in Research and Development:
5-Acetyl-2,4-dimethylthiazole may also be used in research and development settings to study the properties and behavior of heterocyclic thiazoles. This can lead to a better understanding of their potential applications in various fields, such as pharmaceuticals, materials science, or environmental chemistry.

InChI:InChI=1/C7H9NOS/c1-4-7(5(2)9)10-6(3)8-4/h1-3H3

Upstream product

• 64-17-5 ethanol 
• 62-55-5 thioacetamide 
• 1694-29-7 3-chloropentane-2,4-dione 
• 60-35-5 acetamide 
• 89775-33-7 1-(2,4-dimethyl-thiazol-5-yl)-ethanol 
• 40236-03-1 1-(2,4-dimethylthiazol-5-yl)ethan-1-one oxime 
• 7660-21-1 3-chloroacetyl acetone 
• 3043-28-5 3-bromopentane-2,4-dione 

Downstream Products

• 16619-18-4 1-(2,4-dimethyl-thiazol-5-yl)-3-phenyl-propenone 
• 69567-30-2 6-chloro-2-(2,4-dimethyl-thiazol-5-yl)-4-phenyl-quinoline 
• 364334-94-1 4-(2,4-dimethylthiazol-5-yl)pyrimidin-2-ylamine 
• 364334-88-3 N-[4-(2,4-dimethyl-thiazol-5-yl)pyrimidin-2-yl]-N′,N′-dimethylbenzene-1,4-diamine 
• 364333-82-4 {4-(2,4-dimethyl-thiazol-5-yl)-pyrimidin-2-yl}-(3-nitro-phenyl)-amine 

Relevant academic research and scientific papers

Thiazolyl-pyrazole derivatives as potential antimycobacterial agents

Mycobacterium tuberculosis (Mtb) is an obligate aerobe that is capable of long-term persistence under conditions of low oxygen tension. A series of thiazolyl-pyrazole derivatives (6a–f, 7a–f, 8c, 8e) were screened for antimycobacterial activity against dormant M. tuberculosis H37Ra (D-MTB) and M. bovis BCG (D-BCG). Nine thiazolyl-pyrazole analogs, 6c, 6e, 7a, 7b, 7c, 7e, 7f, 8c and 8e exhibited promissing minimum inhibitory concentration (MIC) values (0.20–28.25 μg/mL) against D-MTB and D-BCG strains of Mtb. Importantly, six compounds (7a, 7b, 7e, 7f, 8c and 8e) exhibited excellent antimycobacterial activity and low cytotoxicity at the maximum evaluated concentration of >250 μg/mL. Finally, the promising antimycobacterial activity and lower cytotoxicity profile suggested that, these compounds could be further subjected for optimization and development as a lead, which could have the potential to treat tuberculosis.

Versatile approaches to a library of building blocks based on 5-acylthiazole skeleton

Thiazole derivatives represent an important class of azole heterocycles with a broad spectrum of biological activity and, therefore, the synthesis of these compounds is of remarkable concern. We present here practical and reliable protocol for synthesis of some 5-acylthiazoles and demonstrate their utility in the preparation of several new series of thiazole-containing building blocks through transformation of 5-acyl function. Specifically, thiazole-based alcohols, oximes, primary, and secondary amines were successively synthesized in good to excellent yields. The chemical structures of obtained compounds were confirmed by 1H and 13C NMR-spectroscopy, elemental analysis, and mass-spectrometry.

Discovery of N-Phenyl-4-(thiazol-5-yl)pyrimidin-2-amine aurora kinase inhibitors

Through cell-based screening of our kinase-directed compound collection, we discovered that a subset of N-phenyl-4-(thiazol-5-yl)pyrimidin-2-amines were potent cytotoxic agents against cancer cell lines, suppressed mitotic histone H3 phosphorylation, and caused aberrant mitotic phenotypes. It was subsequently established that these compounds were in fact potent inhibitors of aurora A and B kinases. It was shown that potency and selectivity of aurora kinase inhibition correlated with the presence of a substituent at the aniline para-position in these compounds. The anticancer effects of lead compound 4-methyl-5-(2-(4- morpholinophenylamino)pyrimidin-4-yl)thiazol-2-amine (18; Ki values of 8.0 and 9.2 nM for aurora A and B, respectively) were shown to emanate from cell death following mitotic failure and increased polyploidy as a consequence of cellular inhibition of aurora A and B kinases. Preliminary in vivo assessment showed that compound 18 was orally bioavailable and possessed anticancer activity. Compound 18 (CYC116) is currently undergoing phase I clinical evaluation in cancer patients.

Synthesis and anticancer activities of some thiazole derivatives

In this study, 2-substituted 4-[3/4-(4-arylthiazole-2-yl)aminophenyl] thiazole derivatives and 2-[4-[2-substituted 4-methylthiazole-5-yl]thiazole-2- yl]amino-5-arylidenethiazoline-4-one derivatives have been synthesized. The cytotoxic and/or growth inhibitory effects of the 16 selected compounds were evaluated in vitro against approximately 66 human tumor cell lines derived from nine neoplastic diseases. Some of the compounds were found to act as anticancer agents.

Selective regeneration of carbonyl compounds from aldoximes and ketoximes, catalyzed by FeCl3 and SeO2

An oxidative deblocking procedure of aldoximes using FeCl3 and ketoximes using SeO2 in aprotic solvent is reported. Reaction yields are competitive as compared to previous methods. Reactions are easy to work and conditions are mild. Some important features of FeCl3 are mentioned.

Substituted thiazoles and oxazoles and 2-hydroxy-morpholines

Substituted thiazoles, oxazoles and 2-hydroxy morpholine compounds useful in the treatment of diabetes mellitus and obesity are described.