3161-68-0

Usage

Uses

Used in Pharmaceutical and Chemical Research:
Ethyl 4-Methyl-2-(Methylamino)thiazole-5-carboxylate is utilized as a research compound for exploring its potential biological activities and applications in the development of new pharmaceutical agents.
Used in the Synthesis of Organic Compounds:
Ethyl 4-Methyl-2-(MethylaMino)thiazole-5-carboxylate serves as a building block in the synthesis of various complex organic molecules, leveraging its unique structural features and reactivity.
Used in Antimicrobial Applications:
Ethyl 4-Methyl-2-(Methylamino)thiazole-5-carboxylate is used as an antimicrobial agent, harnessing its potential to inhibit the growth of certain microorganisms, which can be beneficial in various medical and industrial settings.
Used in Antifungal Applications:
Similarly, it is applied as an antifungal agent, where its properties help combat fungal infections, offering a potential solution in the treatment of various fungal-related conditions.
Used in Chemical Industry:
Ethyl 4-Methyl-2-(Methylamino)thiazole-5-carboxylate is used as an intermediate in the chemical industry for the production of other compounds, taking advantage of its reactivity and functional groups for further chemical transformations.

InChI:InChI=1/C8H12N2O2S/c1-4-12-7(11)6-5(2)10-8(9-3)13-6/h4H2,1-3H3,(H,9,10)

Upstream product

• 25348-92-9 Bis-(methylformamidine) disulphide dihydrobromide 
• 141-97-9 ethyl acetoacetate 
• 598-52-7 1-(methyl)-thiourea 
• 609-15-4 ethyl 2-chloro-3-oxo-butyrate 
• 1369787-44-9 C₁₆H₁₈N₂O₄S 

Downstream Products

• 3161-72-6 2-(benzylidene-methyl-hydrazino)-4-methyl-thiazole-5-carboxylic acid ethyl ester 
• 1189558-95-9 4-(4-methyl-2-(methylamino)thiazol-5-yl)-2-(3-nitrophenylamino)pyrimidine-5-carbonitrile 
• 1189558-98-2 3-(5-cyano-4-(4-methyl-2-(methylamino)thiazol-5-yl)pyrimidin-2-ylamino)benzene sulfonamide 
• 1421693-27-7 C₂₂H₂₄N₈OS 
• 1421693-28-8 C₂₀H₂₂N₈S 
• 1421693-29-9 C₂₂H₂₄N₈OS 
• 1421693-30-2 C₂₀H₂₂N₈S 
• 1421693-31-3 C₂₁H₂₃N₇S 
• 1421340-48-8 C₂₃H₂₆N₈OS 
• 1421340-50-2 2-(3-(1,4-diazepan-1-yl)phenylamino)-4-(4-methyl-2-(methylamino) thiazol-5-yl)pyrimidine-5-carbonitrile 

Relevant academic research and scientific papers

Preparation method and application of N-(pyrimidine-2-yl) coumarin-7-amine derivative as protein kinase inhibitor

The invention discloses a cyclin-dependent kinase inhibitor. The cyclin-dependent kinase inhibitor comprises an N-(pyrimidine-2-yl) coumarin-7-amine derivative shown as a general formula (I). In-vitropharmacodynamic tests prove that the compound has a high-selectivity inhibition effect on CDK9 kinase, and can be applied to reducing or inhibiting the activity of CDK9 kinase in cells. The inventionalso discloses a preparation method of the inhibitor and application of the inhibitor in drugs for CDK family kinase mediated diseases, especially hyperproliferative diseases, virus-induced infectious diseases and cardiovascular diseases.

One-Pot Telescoped Synthesis of Thiazole Derivatives from β-Keto Esters and Thioureas Promoted by Tribromoisocyanuric Acid

A simple and efficient one-pot protocol has been developed for the synthesis of thiazole derivatives from readily available starting materials. Tribromoisocyanuric acid was successfully used for α-monohalogenation of β-keto esters in aqueous medium, which

Discovery and pharmacological characterization of a novel series of highly selective inhibitors of cyclin-dependent kinases 4 and 6 as anticancer agents

Background and Purpose: Cyclin D-dependent kinases 4 and 6 (CDK4/6) are crucial regulators of the G1 to S phase transition of the cell cycle and are actively pursued as therapeutic targets in cancer. We sought to discover a novel series of orally bioavailable and highly selective small molecule inhibitors of CDK4/6. Experimental Approach: The discovery of pharmacological inhibitors and optimization for potency, selectivity and drug properties were achieved by iterative chemical synthesis, biochemical screening against a panel of kinases, cell-based assays measuring cellular viability, cell cycle distribution, induction of apoptosis and the level of retinoblastoma tumour suppressor protein (Rb) phosphorylation and E2 factor (E2F)-regulated gene expression and in vitro biopharmaceutical and in vivo pharmacokinetic profiling. Key Results: We discovered several lead compounds that displayed >1000-fold selectivity for CDK4/6 over other members of the CDK family. The lead compounds, 82, 91 and 95, potently inhibited the growth of cancer cells by inducing G1 arrest with a concomitant reduction in the phosphorylation of Rb at S780 and in E2F-regulated gene expression. With a remarkable selectivity for CDK4 over 369 human protein kinases, 91 was identified as a highly potent and orally bioavailable drug candidate. Conclusions and Implications: We have identified unique and new inhibitors of CDK4/6 as potential drug candidates. Compound 91 represents an ideal candidate for further development as targeted cancer therapy.

Synthesis, antitumor activity and mechanism of action of novel 1,3-thiazole derivatives containing hydrazide–hydrazone and carboxamide moiety

A series of novel 2,4,5-trisubstituted 1,3-thiazole derivatives containing hydrazide–hydrazine, and carboxamide moiety including 46 compounds T were synthesized, and evaluated for their antitumor activity in vitro against a panel of five human cancer cell lines. Eighteen title compounds T displayed higher inhibitory activity than that of 5-Fu against MCF-7, HepG2, BGC-823, Hela, and A549 cell lines. Especially, T1, T26 and T38 exhibit best cytotoxic activity with IC50values of 2.21?μg/mL, 1.67?μg/mL and 1.11?μg/mL, against MCF-7, BCG-823, and HepG2 cell lines, respectively. These results suggested that the combination of 1,3-thiazole, hydrazide–hydrazone, and carboxamide moiety was much favorable to cytotoxicity activity. Furthermore, the flow cytometry analysis revealed that compounds T1 and T38 could induce apoptosis in HepG2 cells, and it was confirmed T38 led the induction of cell apoptosis by S cell-cycle arrest.

Substituted 4-(thiazol-5-yl)-2-(phenylamino)pyrimidines are highly active CDK9 inhibitors: Synthesis, X-ray crystal structures, structure-activity relationship, and anticancer activities

Cancer cells often have a high demand for antiapoptotic proteins in order to resist programmed cell death. CDK9 inhibition selectively targets survival proteins and reinstates apoptosis in cancer cells. We designed a series of 4-thiazol-2-anilinopyrimidine derivatives with functional groups attached to the C5-position of the pyrimidine or to the C4-thiazol moiety and investigated their effects on CDK9 potency and selectivity. One of the most selective compounds, 12u inhibits CDK9 with IC50 = 7 nM and shows over 80-fold selectivity for CDK9 versus CDK2. X-ray crystal structures of 12u bound to CDK9 and CDK2 provide insights into the binding modes. This work, together with crystal structures of selected inhibitors in complex with both enzymes described in a companion paper,(34) provides a rationale for the observed SAR. 12u demonstrates potent anticancer activity against primary chronic lymphocytic leukemia cells with a therapeutic window 31- and 107-fold over those of normal B- and T-cells.

Synthesis, structure-activity relationship and biological evaluation of 2,4,5-trisubstituted pyrimidine CDK inhibitors as potential anti-tumour agents

A series of 2,4,5-trisubstituted pyrimidines have been synthesised and characterised, which exhibited potent CDK inhibition and anti-proliferative activities. The structure-activity relationship is analysed and a rational for CDK9 selectivity is discussed

Compounds, compositions and methods

Quinazolinedione derivatives useful for treating cellular proliferative disorders and disorders associated with Kif15 kinesin activity are described.