915019-52-2

Basic information

• Product Name: 4-[(3-amino-6-bromo-4-quinolinyl)amino]-.alpha.,.alpha.-dimethyl-Benzeneacetonitrile
• Synonyms: 4-[(3-amino-6-bromo-4-quinolinyl)amino]-.alpha.,.alpha.-dimethyl-Benzeneacetonitrile;2-(4-(3-aMino-6-broMoquinolin-4-ylaMino)phenyl)-2-Methylpropanenitrile;Benzeneacetonitrile, 4-[(3-aMino-6-broMo-4-quinolinyl)aMino]-a,a-diMethyl-;4-[(3-amino-6-bromo-quinolin-4-yl)amino]-alpha,alpha-dimethylbenzeneacetonitrile
• CAS NO: 915019-52-2
• Molecular Formula: C₁₉H₁₇BrN₄
• Molecular Weight: 381.26908
• Mol File: 915019-52-2.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 528.2°C at 760 mmHg
• Flash Point: 273.3°C
• Appearance: /
• Density: 1.458g/cm³
• Vapor Pressure: 3.03E-11mmHg at 25°C
• Refractive Index: 1.706
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 4-[(3-amino-6-bromo-4-quinolinyl)amino]-.alpha.,.alpha.-dimethyl-Benzeneacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(3-amino-6-bromo-4-quinolinyl)amino]-.alpha.,.alpha.-dimethyl-Benzeneacetonitrile(915019-52-2)
• EPA Substance Registry System: 4-[(3-amino-6-bromo-4-quinolinyl)amino]-.alpha.,.alpha.-dimethyl-Benzeneacetonitrile(915019-52-2)

Safety Data

• Hazardous Substances Data: 915019-52-2(Hazardous Substances Data)

Usage

Uses

2-(4-((3-Amino-6-bromoquinolin-4-yl)amino)-phenyl)-2-methylpropanenitrile is used as a reagent in the preparation of imidazo quinoline derivatives, compounds that act as mammalian target of rapamycin (mTOR) an phosphatidylinositol 3-kinase (PI3K-kinase) inhibitors.

InChI:InChI=1/C19H17BrN4/c1-19(2,11-21)12-3-6-14(7-4-12)24-18-15-9-13(20)5-8-17(15)23-10-16(18)22/h3-10H,22H2,1-2H3,(H,23,24)

Upstream product

• 853908-49-3 5-bromo-2-((2-nitroethenyl)amino)benzoic acid 
• 145369-94-4 6-bromoquinolin-4-ol 
• 187278-01-9 5-(((4-bromophenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 106-40-1 4-bromo-aniline 
• 74189-16-5 2-amino-5-bromobenzoic acid hydrochloride 
• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 1201643-75-5 (E)-5-bromo-2-((2-nitrovinyl)amino)benzoic acid 
• 723281-72-9 6-bromo-4-chloro-3-nitroquinoline 
• 853908-50-6 6-bromo-3-nitroquinolin-4-ol 
• 71825-51-9 4-(2-cyanoprop-2-yl)-1-nitrobenzene 
• 115279-57-7 2-(4-aminophenyl)-2-methylpropionitrile 
• 915019-51-1 2-(4-((6-bromo-3-nitroquinolin-4-yl)amino)phenyl)-2-methylpropanenitrile 

Downstream Products

• 915019-53-3 2-(4-(8-bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-21-2 2-(4-(8-bromo-2-oxo-3-(4-(trifluoromethoxy)phenylsulfonyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-25-6 2-(4-(8-bromo-2-oxo-3-(m-tolylsulfonyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-27-8 2-(4-(8-bromo-3-(2-methyl-5-nitrophenylsulfonyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-30-3 2-(4-(8-bromo-3-(3-fluoro-4-methylphenylsulfonyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-32-5 2-(4-(8-bromo-3-(3,5-dimethylphenylsulfonyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-34-7 2-(4-(8-bromo-2-oxo-3-(phenylsulfonyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-36-9 2-(4-(8-bromo-2-oxo-3-tosyl-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-38-1 2-(4-(8-bromo-2-oxo-3-(thiophen-2-ylsulfonyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-40-5 2-(4-(8-bromo-3-(3-fluorophenylsulfonyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-42-7 2-(4-(8-bromo-2-oxo-3-(quinolin-8-ylsulfonyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-44-9 2-(4-(3-(4-acetylphenylsulfonyl)-8-bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-46-1 2-(4-(8-bromo-2-oxo-3-(3-(trifluoromethyl)phenylsulfonyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 
• 1260167-48-3 2-(4-(8-bromo-3-(3-methoxyphenylsulfonyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile 

Relevant articles and documents

Development of a Robust Synthesis of Dactolisib on a Commercial Manufacturing Scale

The development of the robust synthesis of 2-methyl-2-[4-[3-methyl-2-oxo-8-(quinolin-3-yl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl]-phenyl]propionitrile (dactolisib) on a commercial scale is described. The key step is a Pd-catalyzed Suzuki coupling of 2-[4-(8-bromo-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)-phenyl]-2-methyl-propionitrile to 3-quinoline boronic acid. A special focus is placed on reducing the amount of Pd catalyst used in the Suzuki coupling and purifying the crude drug substance, including removing traces of Pd.

Design, synthesis and biological evaluation of novel phenylsulfonylurea derivatives as PI3K/mTOR dual inhibitors

Five series of novel phenylsulfonylurea derivatives, 19a–d, 20a–d, 21a–d, 22a–d and 23a–d, bearing 4-phenylaminoquinoline scaffold were designed, synthesized and their IC50 values against four cancer cell lines (HepG-2, A549, PC-3 and MCF-7) were evaluated. Most compounds showed moderate cytotoxicity activity against the cancer cell lines. Structure–activity relationships (SARs) and pharmacological results indicated that introduction of 4-aminoquinoline scaffold and phenylsulfonylurea scaffold were beneficial for anti-tumor activity. Moreover, para-methoxyl substitution of 4-anilino moiety and para-halogen substitution of phenylsulfonylurea have different impacts on different series of compounds. Furthermore, the micromolecule group substitution in the 6-position of the quinoline ring have a slight impact on the cellular activity of the target compounds.

Sulfonylurea compound as well as preparation method and application thereof

The invention discloses a sulfonylurea compound, geometrical isomers or pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, and a preparation method thereof. The sulfonylurea compound, the pharmaceutically acceptable salts, hydrates or solvates serving as active ingredients are mixed with pharmaceutically acceptable carriers or excipients to prepare compositions and preparedinto clinically acceptable dosage forms. The invention further discloses application of the compounds in preparation of medicines for treating and/or preventing proliferative diseases, application inpreparation of medicines for treating and/or preventing cancers, and application in preparation of medicines for treating and/or prostatic cancer, lung cancer and breast cancer.