69212-62-0

Basic information

• Product Name: Propanamide, 2,2-dimethyl-N-2-thiazolyl-
• CAS NO: 69212-62-0
• Molecular Formula: C8H12N2OS
• Molecular Weight: 184.25900
• Mol File: 69212-62-0.mol

Chemical Properties

• CAS DataBase Reference: Propanamide, 2,2-dimethyl-N-2-thiazolyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Propanamide, 2,2-dimethyl-N-2-thiazolyl-(69212-62-0)
• EPA Substance Registry System: Propanamide, 2,2-dimethyl-N-2-thiazolyl-(69212-62-0)

Safety Data

• Hazardous Substances Data: 69212-62-0(Hazardous Substances Data)

Upstream product

• 96-50-4 2-thiazolylamine 
• 75-98-9 Trimethylacetic acid 
• 24331-71-3 N,N-dimethylpivalamide 
• 840493-84-7 N-(5-bromothiazol-2-yl)-2,2-dimethylpropanamide 
• 3282-30-2 pivaloyl chloride 

Downstream Products

• 458530-74-0 benzoic acid (2,2-dimethyl-[1,3]dioxolan-4-yl)-[2-(2,2-dimethylpropionylamino)-thiazol-5-yl]-methyl ester 
• 840493-84-7 N-(5-bromothiazol-2-yl)-2,2-dimethylpropanamide 

Relevant articles and documents

Identification of a Multitargeted Tyrosine Kinase Inhibitor for the Treatment of Gastrointestinal Stromal Tumors and Acute Myeloid Leukemia

Gastrointestinal stromal tumors (GISTs) are prototypes of stem cell factor receptor (c-KIT)-driven cancer. Two receptor tyrosine kinases, c-KIT and fms-tyrosine kinase (FLT3), are frequently mutated in acute myeloid leukemia (AML) patients, and these mutations are associated with poor prognosis. In this study, we discovered a multitargeted tyrosine kinase inhibitor, compound 15a, with potent inhibition against single or double mutations of c-KIT developed in GISTs. Moreover, crystal structure analysis revealed the unique binding mode of 15a with c-KIT and may elucidate its high potency in inhibiting c-KIT kinase activity. Compound 15a inhibited cell proliferation and induced apoptosis by targeting c-KIT in c-KIT-mutant GIST cell lines. The antitumor effects of 15a were also demonstrated in GIST430 and GIST patient-derived xenograft models. Further studies demonstrated that 15a inhibited the proliferation of c-KIT- and FLT3-driven AML cells in vitro and in vivo. The results of this study suggest that 15a may be a potential anticancer drug for the treatment of GISTs and AML.

AMINOTHIAZOLE COMPOUNDS AS PROTEIN KINASE INHIBITORS

Aminothiazole compounds of Formula (I) shown below and pharmaceutical compositions containing one of such compounds: Also disclosed are methods of inhibiting a tyrosine kinase and treating cancer associated with a tyrosine kinase with one of the aminothiazole compounds.

SULFONYLAMINOPYRIDINE COMPOUNDS, COMPOSITIONS AND METHODS OF USE

Provided are sulfonylaminopyridine compounds that are inhibitors of ITK kinase, compositions containing these compounds and methods for treating diseases mediated by ITK kinase. In particular, provided are compounds of Formula (I), (II) or (III), stereoisomers, tautomers, solvates, prodrugs or pharmaceutically acceptable salts thereof, where n, R1, R2, R3, R6 and R7 are defined herein, pharmaceutical compositions comprising the compound and a pharmaceutically acceptable carrier, adjuvant or vehicle, methods of using the compound or composition in therapy, for example, for treating a disease or condition mediated by ITK kinase in a patient.

Sulphuric acid immobilized on silica gel (H2SO4-SiO2) as an eco-friendly catalyst for transamidation

A novel method of transamidation of carboxamides with amines by using catalytic amounts of H2SO4-SiO2 has been developed under solvent free conditions. The transamidation is compatible with a wide range of aromatic, heteroaromatic, aliphatic, cyclic/acyclic primary or secondary amines. The metal/solvent-free conditions represent a significant improvement over other existing methods as the reaction can be performed in open air conditions and no column purification is required. The versatility of this methodology was further demonstrated by synthesizing the commercially available drug procainamide.

Potent s-cis-locked bithiazole correctors of ΔF508 cystic fibrosis transmembrane conductance regulator cellular processing for cystic fibrosis therapy

N-(5-(2-(5-Chloro-2-methoxyphenylamino)thiazol-4-yl)-4-methylthiazol-2-yl) pivalamide 1 (compound 15Jf) was found previously to correct defective cellular processing of the cystic fibrosis protein ΔF508-CFTR. Eight C4′-C5 C,C-bond-controlling bithiazole analogues of 1 were designed, synthesized, and evaluated to establish that constraining rotation about the bithiazole-tethering has a significant effect on corrector activity. For example, constraining the C4′-C5 bithiazole tether in the s-cis conformation [N-(2-(5-chloro-2- methoxyphenylamino)-7,8-dihydro-6H-cyclohepta[1,2-d:3,4-d′] bithiazole-2′-yl)pivalamide, 29] results in improved corrector activity. Heteroatom placement in the bithaizole core is also critical as evidenced by the decisive loss of corrector activity with s-cis constrained N-(2-(5-chloro-2- methoxyphenylamino)-5,6-dihydro-4H-cyclohepta[1,2-d:3,4-d′] bithiazole-2′-yl)pivalamide 33. In addition, computational models were utilized to examine the conformational preferences for select model systems. Following our analysis, the "s-cis-locked" cycloheptathiazolothiazole 29 was found to be the most potent bithiazole corrector, with an IC50 of ～450 nM.

AMINOTHIAZOLE DERIVATIVES AS INHIBITORS OF MARK

Compounds of formula (I): inhibit microtubule affinity regulating kinase (MARK) and therefore find use in treatment of neurodegenerative diseases associated with hyperphosphorylation of tau.

Investigations of the halogen dance reaction on N-substituted 2-thiazolamines

(Chemical Equation Presented) The halogen dance (HD) reaction on various 2-thiazolamine systems was investigated providing an easy access to a series of 5-substituted 4-bromo-2-thiazolamine derivatives. We could show that HD is a very favored process for

Synthesis of 5-deazathiogirollines: Analogs of a natural antitumor agent

2-Aminothiazole analogs of the natural antitumor agent, girolline, were prepared in natural stereochemistry series (threo) and in a non-natural series (erythro). The key-step involved a coupling reaction between 2,3-O-isopropylidene-D-glyceraldehyde and a properly protected 2-aminothiazole, via a dianion species. The biological activity of the prepared analogs was evaluated on human cancer cells to determine structure-activity relationship.