16849-91-5

Usage

Purification Methods

Crystallise the (+)-urea from H2O or EtOH (m122-123o). [Marckwald & Meth Chem Ber 38 808 1905, Cairns J Am Chem Soc 63 871 1941, Beilstein 12 I 1092, 1

InChI:InChI=1/C9H12N2O/c1-7(11-9(10)12)8-5-3-2-4-6-8/h2-7H,1H3,(H3,10,11,12)

Upstream product

• 33375-06-3 (1R)-1-phenylethyl isocyanate 
• 590-28-3 potassium cyanate 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 556-89-8 nitrourea 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 57-13-6 urea 
• 2158-03-4 1-piperidinecarboxamide 
• 2158-02-3 morpholine-4-carboxylic acid amide 

Downstream Products

• 90545-52-1 3-(R)-(+)-α-methylbenzylbarbituric acid 
• 90545-54-3 6-chloro-5-formyl-(R)-3α-methylbenzyluracil 
• 90545-56-5 (+)-10-butyl-3-(R)-α-methylbenzyl-5-deazaflavin 
• 112983-35-4 (+)-8,9-benzo-10-butyl-3-(R)-α-methylbenzyl-5-deazaflavin 
• 112983-33-2 (+)-10-butyl-7-methyl-3-(R)-α-methylbenzyl-5-deazaflavin 
• 90545-58-7 10-Butyl-3-((R)-1-phenyl-ethyl)-5,10-dihydro-1H-pyrimido[4,5-b]quinoline-2,4-dione 
• 353746-20-0 (4S)-4-(3,4-Difluorophenyl)-5,5-dimethyl-3-[(4'-(4-fluorophenyl)-piperidin-1'-yl)propyl]aminocarbonyltetrahydropyrimidin-2-one Hydrochloride 
• 1452864-25-3 C₂₅H₂₇N₅O₂ 
• 1327280-57-8 C₂₃H₃₀N₂O₁₀ 
• 60325-13-5 (+)-(R)-1-Phenyl-aethylhydrazin 
• 60325-12-4 N'-[(R)-1-phenylethyl]hydrazinecarboxylic acid t-butyl ester 

Relevant academic research and scientific papers

Discovery of 1-(1H-Pyrazolo[4,3-c]pyridin-6-yl)urea Inhibitors of Extracellular Signal-Regulated Kinase (ERK) for the Treatment of Cancers

The ERK/MAPK pathway plays a central role in the regulation of critical cellular processes and is activated in more than 30% of human cancers. Specific BRAF and MEK inhibitors have shown clinical efficacy in patients for the treatment of BRAF-mutant melanoma. However, the majority of responses are transient, and resistance is often associated with pathway reactivation of the ERK signal pathway. Acquired resistance to these agents has led to greater interest in ERK, a downstream target of the MAPK pathway. De novo design efforts of a novel scaffold derived from SCH772984 by employing hydrogen bond interactions specific for ERK in the binding pocket identified 1-(1H-pyrazolo[4,3-c]pyridin-6-yl)ureas as a viable lead series. Sequential SAR studies led to the identification of highly potent and selective ERK inhibitors with low molecular weight and high LE. Compound 21 exhibited potent target engagement and strong tumor regression in the BRAFV600E xenograft model.

Ammonium Chloride-Promoted Rapid Synthesis of Monosubstituted Ureas under Microwave Irradiation

Monosubstituted ureas are important scaffolds in organic chemistry. They appear in various biologically active compounds and serve as versatile precursors in synthesis. Monosubstituted ureas were originally prepared using toxic and hazardous phosgene equivalents. Modern methods include transamidation of urea and nucleophilic addition to cyanate salts, both of which suffer from a narrow substrate scope due to the need for a strong acid and prolonged reaction times. We hereby report that ammonium chloride can promote the reaction between amines and potassium cyanate to generate monosubstituted ureas in water. This method proceeds rapidly under microwave irradiation and tolerates a broad range of functional groups. Unlike previous strategies, it is compatible with other nucleophiles, acid-labile moieties, and most of the common protecting groups. The products precipitate out of solution, allowing facile isolation without column chromatography.

Regioselective Formal [3+2] Cycloadditions of Urea Substrates with Activated and Unactivated Olefins for Intermolecular Olefin Aminooxygenation

A new class of intermolecular olefin aminooxygenation reaction is described. This reaction utilizes the classic halonium intermediate as a regio- and stereochemical template to accomplish the selective oxyamination of both activated and unactivated alkenes. Notably, urea chemical feedstock can be directly introduced as the N and O source and a simple iodide salt can be utilized as the catalyst. This formal [3+2] cycloaddition process provides a highly modular entry to a range of useful heterocyclic products with excellent selectivity and functional-group tolerance.

NOVEL COMPOUNDS THAT ARE ERK INHIBITORS

Disclosed are the ERK inhibitors of formula (1): and the pharmaceutically acceptable salts thereof. Also disclosed are methods of treating cancer using the compounds of formula (1).

Nano-Magnetic Sulfonic Acid Catalyzed Facile Synthesis of Diverse Amide Derivatives

The excellent surface catalytic potential of Fe3O4-OSO3H is utilized in the synthesis of symmetrically and unsymmetrically substituted urea derivatives via transamidation reactions. The scope of the surface catalysis is further extended in transamidation reactions of cyclic and acyclic amide derivatives, and in the amidation of fatty acids. In both transamidation and amidation reactions, the catalyst is reusable up to five times without significant loss in its activity.

NOVEL COMPOUNDS THAT ARE ERK INHIBITORS

Disclosed are the ERK inhibitors of formula (1): and the pharmaceutically acceptable salts thereof. Also disclosed are methods of treating cancer using the compounds of formula (1)

SEVEN-MEMBERED RING COMPOUND, PRODUCTION METHOD THEREOF AND PHARMACEUTICAL USE THEREOF

A 7-membered heterocyclic compound having the formula (I), or its salt, or a solvate thereof with a chymase inhibitory action and useful for the prevention or treatment of various diseases, in which chymase is involved: a method for producing the same, and a pharmaceutical composition useful for the prevention or treatment of diseases, in which chymase is involved, including the compound of having the formula (I), or its pharmaceutically acceptable salt, or a solvate thereof are provided.

7-MEMBERED RING COMPOUND, PROCESS FOR PRODUCING THE SAME, AND MEDICINAL USE THEREOF

A 7-membered heterocyclic compound having the formula (I), or its salt, or a solvate thereof with a chymase inhibitory action and useful for the prevention or treatment of various diseases, in which chymase is involved: a method for producing the same, and a pharmaceutical composition useful for the prevention or treatment of diseases, in which chymase is involved, including the compound of having the formula (I), or its pharmaceutically acceptable salt, or a solvate thereof are provided.

PREPARATION OF CHIRAL 5-DEAZAFLAVIN DERIVATIVES AND THEIR ASYMMETRIC REDUCTION OF ETHYL BENZOYLFORMATE

1,5-Dihydro-5-deazaflavin derivatives possessing a chiral substituent at N(3) position were synthesized, with which moderate asymmetric induction was observed in the reduction of ethyl benzoilformate.