13230-13-2

Usage

Synthesis Reference(s)

Synthetic Communications, 19, p. 1309, 1989 DOI: 10.1080/00397918908054539

InChI:InChI=1/C11H9N3O3/c15-7-10-11(14(16)17)12-8-13(10)6-9-4-2-1-3-5-9/h1-5,7-8H,6H2

Upstream product

• 3034-38-6 1H-4⁽⁵⁾-nitroimidazole 
• 620-05-3 iodomethylbenzene 
• 19182-81-1 1,4-dinitro-1H-imidazole 
• 100-46-9 benzylamine 
• 100-44-7 benzyl chloride 
• 3034-38-6 5-nitro-1H-imidazole 
• 100-39-0 benzyl bromide 
• 126401-72-7 tetrabutylammonium 4⁽⁵⁾-nitroimidazole 

Downstream Products

• 161091-87-8 1-benzyl-4-nitroimidazol-5-ylacetonitrile 
• 154927-05-6 3-benzyl-5-nitro-3H-imidazole-4-carbaldehyde 
• 748813-21-0 diethyl 2-(3-benzyl-5-nitro-3H-imidazol-4-ylmethylene)malonate 
• 145838-72-8 1-benzyl-4-(2,3-dimethoxycarbonyl-5-ethoxycarbonyl-4-oxo-1,4-dihydro-1-pyridyl)imidazole 
• 145838-71-7 ethyl 2-(1-benzyl-3,4-dimethoxycarbonylpyrrol-2-yl)-4-oxo-3,4-dihydropyrimidine-5-carboxylate 
• 145838-70-6 7-benzyl-3-ethoxycarbonylimidazo<3,4-a>pyrimidin-7-ium-4-olate 
• 161091-90-3 1-benzyl-4-nitroimidazole-5-carboxime 
• 161091-99-2 4-amino-1-benzylimidazole-5-carboxime 
• 161091-89-0 4-amino-1-benzylimidazole-5-carbaldehyde 
• 4059-11-4 1-benzyl-4-nitroimidazole-5-carbonitrile 

Relevant academic research and scientific papers

NOVEL COMPOUNDS

The present invention relates to novel compounds and methods for the manufacture of inhibitors of deubiquitylating enzymes (DUBs). In particular, the invention relates to the inhibition of ubiquitin C-terminal hydrolase L1 (UCHL1). The invention further relates to the use of DUB inhibitors in the treatment of cancer and other indications. Compounds of the invention include compounds having the formula (I) or a pharmaceutically acceptable salt thereof, wherein R1 to R8 are as defined herein.

Identification of Aminoimidazole and Aminothiazole Derivatives as Src Family Kinase Inhibitors

Src family kinases (SFKs) are a family of non-receptor tyrosine kinases (TKs) implicated in the regulation of many cellular processes. The aberrant activity of these TKs has been associated with the growth and progression of cancer. In particular, c-Src i

C-H arylation of nitroimidazoles and nitropyrazoles guided by the electronic effect of the nitro group

A palladium-catalyzed C-H arylation reaction of nitroimidazoles and nitropyrazoles was developed using aryl bromides as arene donors. The electron-withdrawing effect of the nitro group allows for direct C-H arylation reactions of the nitro diazoles with h

Facile synthesis of fluorinated 1-desazapurines

A preparative approach towards 1-desazapurines, starting from 4(5)-aminoimidazoles and polyfluoroalkyl-containing 1,3-CCC-biselectrophiles was developed. As a result, a set of fluorinated 1-desazapurines was synthesized. Additionally, a synthetic route to 1-desazapurines bearing a sugar-mimicking group is proposed. Georg Thieme Verlag Stuttgart.

Potent and cellularly active 4-aminoimidazole inhibitors of cyclin-dependent kinase 5/p25 for the treatment of Alzheimer's disease

Utilizing structure-based drug design, a 4-aminoimidazole heterocyclic core was synthesized as a replacement for a 2-aminothiazole due to potential metabolically mediated toxicity. The synthetic route utilized allowed for ready synthesis of 1-substituted-4-aminoimidazoles. SAR exploration resulted in the identification of a novel cis-substituted cyclobutyl group that gave improved enzyme and cellular potency against cdk5/p25 with up to 30-fold selectivity over cdk2/cyclin E.

Synthesis of a new imidazo[4,5-b]pyridin-5-one via a vicarious nucleophilic substitution of hydrogen

A new imidazo [4,5-b]pyridin-5-one was prepared in five steps from 4(5)-nitro-1H-imidazole via a vicarious nucleophilic substitution of hydrogen of 1-benzyl-4-nitro-1H-imidazole with the carbanion generated from chloroform and potassium tert-butoxide. Hydrolysis of 1-benzyl-5-dichloromethyl-4-nitro-1H- imidazole and Knoevenagel condensation between the resulting aldehyde and diethyl malonate catalyzed by titanium(IV) chloride gave the corresponding 4-nitroimidazole bearing at 4 position the diethyl methylenemalonate group. Reduction and cyclization afforded the required ethyl 1-benzyl-5-oxo-4,5- dihydro-1H-imidazo[4,5-b]pyridine-6-carboxylate.

Electrochemical reduction of 1-aryl-4-nitroazoles

Electrochemical reduction of the nitro group in 1-aryl-4-nitroazoles occurs in slightly acidic medium as a typical four-electron process leading to hydroxylamine group formation. The forming 1-aryl-4-hydroxylaminoazoles undergo further reactions. Stabilit

Regioselective Alkylation of 4(5)-Nitro-1H-Imidazoles in Acidic Media: Study of Temperature Effects

Alkylation of 4(5)-nitro-1H-imidazoles in acidic media with reactive alkylating agents such as benzyl chloride and allyl bromide resulted in the predominant formation of the 5-nitro isomers at lower temperatures (75 deg C) and the 4-nitro isomers at higher temperatures (140 deg C).With less reactive alkylating agents, only the 5-nitro isomers were produced irrespective of temperature.The mechanism was shown to involve quaternization of the initially formed 1-alkyl-5-nitro-1H-imidazoles followed by preferential dealkylation to yield the thermodynamically more stable 4-nitro-1H-imidazoles.

Dihalomethylation of Nitroarenes via Vicarious Nucleophilic Substitution of Hydrogen with Trihalomethyl Carbanions

Trichloro- and tribromomethyl carbanions generated by deprotonation of haloforms with potassium tert-butoxide in a THF-DMF mixture at ca. -70 deg C react with a variety of carbocyclic and heterocyclic nitroarenes according to the vicarious nucleophilic substitution scheme.The reaction provides an efficient and convenient way for the direct introduction of dihalomethyl substituents ortho and para to the nitro group, which in turn can be hydrolyzed to produce nitroaryl aldehydes.