107392-72-3

Usage

Structure

Heterocyclic aromatic ring structure with an imidazole core

Usage

Research and development of pharmaceuticals
Exploration as a serotonin receptor agonist
Investigated for potential use in anxiety, depression, and other psychological disorders
Potential applications in neuropharmacology
Tool for studying serotonin receptors and related pathways

Upstream product

• 42564-22-7 2-phenyl-5,6,7,7a-tetrahydro-3H-pyrrolo[2,1-a]imidazol-1-oxide 
• 42564-18-1 3-phenyl-6,7,8,8a-tetrahydro-4H-pyrrolo[1,2-e][1,2,5]oxadiazine 
• 876149-81-4 1-hydroxy-2-phenyl-perhydropyrrolo[1,2-a]imidazole 
• 7544-75-4 2-iminopyrrolidine-hydrochloride 
• 70-11-1 α-bromoacetophenone 
• 91417-91-3 2-Chloro-5H,6,7-dihydropyrrolo<1,2-a>imidazole 
• 98-80-6 phenylboronic acid 
• 7491-74-9 2-oxo-1-pyrrolidine acetamide 

Downstream Products

• 883233-75-8 BrH*C₁₂H₁₁BrN₂ 
• 107392-82-5 3-bromo-2-phenyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole 

Relevant academic research and scientific papers

Discovery of Potent 2-Aryl-6,7-dihydro-5 H-pyrrolo[1,2- a]imidazoles as WDR5-WIN-Site Inhibitors Using Fragment-Based Methods and Structure-Based Design

WDR5 is a chromatin-regulatory scaffold protein overexpressed in various cancers and a potential epigenetic drug target for the treatment of mixed-lineage leukemia. Here, we describe the discovery of potent and selective WDR5-WIN-site inhibitors using fragment-based methods and structure-based design. NMR-based screening of a large fragment library identified several chemically distinct hit series that bind to the WIN site within WDR5. Members of a 6,7-dihydro-5H-pyrrolo[1,2-a]imidazole fragment class were expanded using a structure-based design approach to arrive at lead compounds with dissociation constants 10 nM and micromolar cellular activity against an AML-leukemia cell line. These compounds represent starting points for the discovery of clinically useful WDR5 inhibitors for the treatment of cancer.

Imidazole Compound

An imidazole compound of the formula: wherein Ring A is benzene or a heterocyclic ring; G is alkylthio, alkylsulfonyl, optionally substituted phenyl, or optionally substituted heterocyclic ring group, etc.; Ring C is imidazole; R1 is carbamoyl, etc.; R2 is cyano, nitro, hydroxyl, an alkoxy, a halogen, carboxy, an alkoxycarbonyl, carbamoyl, amino, an alkyl, etc.; m is 0 to 2; and R4 is hydrogen, an alkyl, etc., or a pharmaceutically acceptable salt thereof, is a large conductance calcium-activated K channel opener useful for treatment of pollakiuria, urinary incontinence, etc.

KINASE INHIBITORS

ABSTRACT The present invention provides kinase inhibitors of Formula I: .

Hydroxylamine function as neighboring group with dehydrogenations

The β-amino-hydroxylamines 5a-d are prepared of the α-amino-oximes 1a-d with borane-dimethylsulfide. With mercury-EDTA, 5a-d react to (E/Z)-oxime-lactams 3a-d and benzaldoxime 7. Additionally 5b,c give the bicyclic amidine-N-oxides 8b,c, which slowly hydrolyze to the hydroxylamine-lactams 9b,c. These are easily oxidized to (E/Z)-3b,c. Postulated as intermediates in the mercury-assisted reduction of 5, the cyclic hydroxylamines 10a-d are available from the nitrones 4a-d with LiAlH 4. From 10a-d with mercury-EDTA the same products are obtained as from 5a-d but without 7. Only the pyrrolidine 10a forms besides (E/Z)-3a the nitrone 4a. Thin-layer chromatography shows that the pure isomers of 3a-d in solution isomerize, contrary to the amine-oximes 1a-d. The configuration of the oxime-lactams depends on the manner of preparation. With mercury-EDTA, 1b,c yield 3b,c with retention of the configuration, while the oximation of phenacyl-lactams 13b,c give rise to (E/Z)-mixtures of 3b,c. The condensed imidazoles 12 result from the nitrones 4a-d and the dihydrooxadiazines 2a,d on treatment with hydrogen chloride.