175168-71-5

Basic information

• Product Name: Cyclopropanecarboxylic acid, 2-(2-fluorophenyl)-, (1R,2R)-rel-
• Synonyms: Cyclopropanecarboxylic acid, 2-(2-fluorophenyl)-, (1R,2R)-rel-
• CAS NO: 175168-71-5
• Molecular Formula: C10H9FO2
• Molecular Weight: 180.17600
• Mol File: 175168-71-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 293.6±40.0 °C(Predicted)
• Density: 1.345±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Cyclopropanecarboxylic acid, 2-(2-fluorophenyl)-, (1R,2R)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanecarboxylic acid, 2-(2-fluorophenyl)-, (1R,2R)-rel-(175168-71-5)
• EPA Substance Registry System: Cyclopropanecarboxylic acid, 2-(2-fluorophenyl)-, (1R,2R)-rel-(175168-71-5)

Safety Data

• Hazardous Substances Data: 175168-71-5(Hazardous Substances Data)

Upstream product

• 104201-65-2 methyl (2E)-3-(2-fluorophenyl)prop-2-enoate 
• 18944-77-9 2-fluorocinnamic acid 
• 455267-55-7 methyl 2-(2-fluorophenyl)cyclopropanecarboxylate 
• 348-52-7 1-Fluoro-2-iodobenzene 
• 372183-83-0 3-(2-fluoro-phenyl)-N-methoxy-N-methyl-acrylamide 

Relevant articles and documents

Selective 5-hydroxytryptamine 2c receptor agonists derived from the lead compound tranylcypromine: Identification of drugs with antidepressant-like action

We report here the design, synthesis, and pharmacological properties of a series of compounds related to tranylcypromine (9), which itself was discovered as a lead compound in a high-throughput screening campaign. Starting from 9, which shows modest activity as a 5-HT2C agonist, a series of 1-aminomethyl-2- phenylcyclopropanes was investigated as 5-HT2C agonists through iterative structural modifications. Key pharmacophore feature of this new class of ligands is a 2-aminomethyl-trans-cyclopropyl side chain attached to a substituted be zene ring. Among the tested compounds, several were potent and efficacious 5-HT2C receptor agonists with selectivity over both 5-HT2A and 5-HT2B receptors in functional assays. The most promising compound is 37, with 120- and 14-fold selectivity over 5-HT 2A and 5-HT2B, respectively (EC50) 585, 65, and 4.8 nM at the 2A, 2B, and 2C subtypes, respectively). In animal studies, compound 37 (10-60 mg/kg) decreased immobility time in the mouse forced swim test.

Arylcyclopropylcarboxylic amides as potassium channel openers

The present invention provides novel arylcyclopropylcarboxylic amides and related derivatives having the general Formula I wherein R, R1, R2, R3, R4, R5, R6 and R7 are as defined

trans-2-Aryl-N,N-dipropylcyclopropylamines: Synthesis and interactions with 5-HT(1A) receptors

Twelve N,N-dipropyl-substituted derivatives of trans-2- arylcyclopropylamine have been prepared and assayed for their ability to displace [3H]-8-OH-DPAT from rat brain 5-HT(1A) receptors. The new derivatives include phenyl (7a), bromo- (7b) and fluorophenyl (7c-e), 2- methoxy-5-fluorophenyl (7h), and 2-hydroxy-5-fluorophenyl (71) as well as trifluoromethylphenyl (7f) and 2,3-dichlorophenyl (7g) analogues. In the present series of compounds, electron-withdrawing substituents in the phenyl ring appear to decrease the affinity for 5-HT(1A) receptors. In contrast, electron-rich aryl groups, such as 2- or 3-thienyl (7j and 7k, respectively), provide compounds with high affinity. The additional bulk produced by the aromatic moiety in the 2-benzothienyl derivative 7i appears to be detrimental to 5-HT(1A) receptor affinity. The racemic mixtures of the interesting 7j and 7l were resolved into the enantiomers; 7j and 7l exhibited a high enantiomeric 5-HT(1A) receptor affinity ratio (75-fold and 100-fold, respectively). The enantiomers of 7j and 7l were evaluated in vivo by use of biochemical and behavioral tests in rats. Compound (1R,2R)-7j behaved as a partial agonist whereas (1R,2S)-7l appeared as an efficacious 5-HT(1A) receptor agonist, stimulating both autoreceptors and postsynaptic receptors.