763126-74-5

Basic information

• Product Name: (1R,2S)-1,2-di(hydroxymethyl)-2-phenylcyclopropane
• Synonyms: (1R,2S)-1,2-di(hydroxymethyl)-2-phenylcyclopropane
• CAS NO: 763126-74-5
• Molecular Weight: 178.231
• Mol File: 763126-74-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (1R,2S)-1,2-di(hydroxymethyl)-2-phenylcyclopropane(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-1,2-di(hydroxymethyl)-2-phenylcyclopropane(763126-74-5)
• EPA Substance Registry System: (1R,2S)-1,2-di(hydroxymethyl)-2-phenylcyclopropane(763126-74-5)

Safety Data

• Hazardous Substances Data: 763126-74-5(Hazardous Substances Data)

Upstream product

• 63106-93-4 (1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one 
• 140-29-4 phenylacetonitrile 

Downstream Products

• 1383746-33-5 (1R,2S)-2-[(1,3-dimethyl-6-oxo-1,6-dihydropyridazin-4-yl)oxymethyl]-N-(5-methoxypyridin-3-yl)-2-phenylcyclopropanecarboxamide 
• 1383746-49-3 (1R,2S)-2-[2-(3-difluoromethyl-5-methyl-1H-1,2,4-triazol-1-yl)ethyl]-N-(5-fluoro-4-methylpyridin-2-yl)-2-phenylcyclopropanecarboxamide 
• 1383747-26-9 tert-Butyl-{[(1R,2S)-2-bromomethyl-2-phenylcyclopropyl]methoxy}diphenylsilane 
• 1383747-28-1 5-{[(1S,2R)-2-Hydroxymethyl-1-phenylcyclopropyl]methoxy}-2,6-dimethyl-2H-pyridazin-3-one 
• 1383747-56-5 (1R,2S)-2-[2-(3-difluoromethyl-5-methyl-1H-1,2,4-triazol-1-yl)ethyl}-2-phenylcyclopropanecarboxylic acid 
• 1383747-53-2 {(1R,2S)-2-[2-(3-Difluoromethyl-5-methyl-1H-1,2,4-triazol-1-yl)ethyl]-2-phenylcyclopropyl}methyl pivalate 
• 1383747-54-3 {(1R,2S)-2-[2-(3-Difluoromethyl-5-methyl-1H-1,2,4-triazol-1-yl)ethyl]-2-phenylcyclopropyl}methanol 
• 1383747-55-4 (1R,2S)-2-[2-(3-Difluoromethyl-5-methyl-1H-1,2,4-triazol-1-yl)ethyl]-2-phenylcyclopropanecarbaldehyde 
• 1383746-10-8 (-)-N-(5-cyanopyridin-2-yl)-2-[(1-ethyl-3-methyl-1H-pyrazol-4-yl)oxymethyl]-2-phenylcyclopropanecarboxamide 
• 1383747-29-2 (1R,2S)-2-((1,3-dimethyl-6-oxo-1,6-dihydropyridazin-4-yl)oxymethyl)-2-phenylcyclopropanecarbaldehyde 
• 1383747-30-5 (1R,2S)-2-((1,3-dimethyl-6-oxo-1,6-dihydropyridazin-4-yl)oxymethyl)-2-phenylcyclopropanecarboxylic acid 
• 1369764-47-5 (1R,2S)-N-(5-cyanopyridin-2-yl)-2-{[(4-(methoxymethyl)-2-methylpyrimidin-5-yl)oxy]methyl}-2-phenylcyclopropanecarboxamide 
• 1383746-08-4 (1R,2S)-N-(5-cyanopyridin-2-yl)-2-(((3,5-dimethylpyrazin-2-yl)oxy)methyl)-2-phenylcyclopropanecarboxamide 
• 1369764-27-1 (1R,2S)-N-(5-cyanopyridin-2-yl)-2-(((4-ethyl-2-methylpyrimidin-5-yl)oxy)methyl)-2-phenylcyclopropanecarboxamide 

Relevant articles and documents

Discovery of (1R,2S)-2-{[(2,4-Dimethylpyrimidin-5-yl)oxy]methyl}-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide (E2006): A Potent and Efficacious Oral Orexin Receptor Antagonist

The orexin/hypocretin receptors are a family of G protein-coupled receptors and consist of orexin-1 (OX1) and orexin-2 (OX2) receptor subtypes. Orexin receptors are expressed throughout the central nervous system and are involved in the regulation of the sleep/wake cycle. Because modulation of these receptors constitutes a promising target for novel treatments of disorders associated with the control of sleep and wakefulness, such as insomnia, the development of orexin receptor antagonists has emerged as an important focus in drug discovery research. Here, we report the design, synthesis, characterization, and structure-activity relationships (SARs) of novel orexin receptor antagonists. Various modifications made to the core structure of a previously developed compound (-)-5, the lead molecule, resulted in compounds with improved chemical and pharmacological profiles. The investigation afforded a potential therapeutic agent, (1R,2S)-2-{[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-2-(3-fluorophenyl)-N-(5-fluoropyridin-2-yl)cyclopropanecarboxamide (E2006), an orally active, potent orexin antagonist. The efficacy was demonstrated in mice in an in vivo study by using sleep parameter measurements. (Chemical Equation Presented).

CYCLOPROPANE DERIVATIVES

A cyclopropane derivative represented by the following formula (I) or a pharmaceutically acceptable salt thereof has orexin receptor inhibitory action, and thus, is extremely useful as an agent for preventing or treating sleep disorder or dyssomnia caused by orexin, including insomnia as a typical example: wherein A1, A2 and A3 each independently represent an aryl group, a heterocyclyl group or the like, R1, R2 and R3 each independently represent a hydrogen atom, a C1-6 alkyl group or the like, X represents an oxygen atom or the like, and L represents a bond or the like.