752243-39-3

Basic information

• Product Name: 6-[7(R)-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthamide
• Synonyms: 6-[7(R)-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthamide;TAK-700 (R-form);6-[(7R)-7-hydroxy-5,6-dihydropyrrolo[1,2-c]imidazol-7-yl]-N-methylnaphthalene-2-carboxamide
• CAS NO: 752243-39-3
• Molecular Formula: C18H17N3O2
• Molecular Weight: 307.34648
• Mol File: 752243-39-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.35
• CAS DataBase Reference: 6-[7(R)-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthamide(CAS DataBase Reference)
• NIST Chemistry Reference: 6-[7(R)-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthamide(752243-39-3)
• EPA Substance Registry System: 6-[7(R)-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthamide(752243-39-3)

Safety Data

• Hazardous Substances Data: 752243-39-3(Hazardous Substances Data)

Usage

General Description

6-[7(R)-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl]-N-methyl-2-naphthamide is a chemical compound with the molecular formula C21H19N3O2. It is a derivative of naphthamide and contains a pyrroloimidazol backbone. The compound has a hydroxy group and a methyl group attached to the pyrroloimidazol ring, giving it unique properties and potential applications in drug discovery and development. The precise pharmacological and physiological effects of this compound are not well characterized, but its structure suggests that it may have potential as a drug target for a variety of diseases and conditions. Further research is needed to fully understand the properties and potential uses of this chemical.

Upstream product

• 426219-43-4 5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one 
• 87700-60-5 6-bromonaphthalene-2-carbonyl chloride 
• 5773-80-8 6-bromo-2-naphthoic acid 
• 57531-35-8 C₆H₆N₂O 
• 1346155-45-0 3-bromo-1-(1H-imidazol-4-yl)-1-propanone hydrobromide 
• 1346155-60-9 6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N,N-diisopropyl-2-naphthamide 
• 426219-47-8 N,N-diisopropyl-6-[(1-trityl-1H-imidazol-4-yl)carbonyl]-2-naphthamide 
• 1346155-54-1 N,N-diisopropyl-6-[1-hydroxy-1-(1-trityl-1H-imidazol-4-yl)methyl]-2-naphthamide 
• 426219-18-3 orteronel 
• 426219-35-4 6-bromo-N-methyl-2-naphthamide 
• 426219-46-7 6-bromo-N,N-diisopropyl-2-naphthamide 

Relevant articles and documents

Multistep Binding of the Non-Steroidal Inhibitors Orteronel and Seviteronel to Human Cytochrome P450 17A1 and Relevance to Inhibition of Enzyme Activity

Orteronel (TAK-700) is a substituted imidazole that was developed for the treatment of castration-resistant prostate cancer but was dropped in phase III clinical trials. Both enantiomers of this inhibitor of cytochrome P450 (P450) 17A1 show some selectivity in differentially blocking the 17α-hydroxylation and lyase activities of the enzyme. Although both enantiomers of this compound have sub-micromolar IC50 values and bind to the enzyme with a type II spectral change (indicative of nitrogen-iron bonding) and reported Kd values of 56 and 40 nM (R and S, respectively), the rates of binding to P450 17A1 were relatively slow. We considered the possibility that the drug is a slow, tight-binding inhibitor. Analysis of the kinetics of binding revealed rapid formation of an initial complex, presumably in the substrate binding site, followed by a slower change to the spectrum of a final iron complex. Similar kinetics were observed in the interaction of another inhibitor, the triazole (S)-seviteronel (VT-464), with P450 17A1. Kinetic tests and modeling indicate that the further change to the iron-complexed form of the orteronel- or seviteronel-P450 complex is not a prerequisite for enzyme inhibition. Accordingly, the inclusion of heme-binding heterocyclic nitrogen moieties in P450 17A1 inhibitors may not be necessary to achieve inhibition but may nevertheless augment the process.

1,1-Diarylalkenes as anticancer agents: Dual inhibitors of tubulin polymerization and phosphodiesterase 4

A series of 1,1-diarylalkene derivatives were prepared to optimize the properties of CC-5079 (1), a dual inhibitor of tubulin polymerization and phosphodiesterase 4 (PDE4). By using the 3-ethoxy-4-methoxyphenyl PDE4 pharmacophore as one of the aromatic ri