1157561-41-5

Usage

Uses

Used in Pharmaceutical Industry:
2-(3-Fluoro-phenyl)-cyclopropanecarboxylic acid is used as a reactant for the preparation of N-acyl-4-(heterocyclylaminomethyl)piperidines. These compounds serve as NMDA/NR2B antagonists, which are important in the development of medications targeting neurological disorders such as Alzheimer's disease, Parkinson's disease, and chronic pain conditions. The unique structure of 2-(3-Fluoro-phenyl)-cyclopropanecarboxylic acid contributes to the effectiveness of these antagonists by modulating the activity of the NMDA receptor, a key player in synaptic plasticity and neuronal function.

Upstream product

• 1121-86-4 1-Fluoro-3-iodobenzene 
• 263893-75-0 ethyl 2-(3-fluorophenyl)cyclopropane carboxylate 
• 1759-53-1 cyclopropanecarboxylic acid 
• 74325-03-4 methyl (E)-m-fluorocinnamate 
• 350-51-6 3-fluorostyrene 
• 243665-11-4 (2E)-3-(3-fluorophenyl)-N-methoxy-N-methylmethylacrylamide 
• 351-46-2 3-(3-Fluorophenyl)acrylic acid ethyl ester 
• 456-48-4 3-Fluorobenzaldehyde 
• 20595-30-6 3-Fluorocinnamic acid 

Downstream Products

• 1417656-40-6 (1S,2S)-2-(3-fluorophenyl)-cyclopropanecarboxylic acid 
• 1424142-93-7 C₃₇H₅₅FN₄O₇ 
• 1237495-00-9 (1S,2R)-2-(3-fluorophenyl)cyclopropanamine 
• 220353-83-3 (1R,2S)-2-(3-fluorophenyl)cyclopropanamine 
• 1237495-03-2 (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-((1S,2R/1R,2S)-2-(3-fluorophenyl)cyclopropylamino)ethoxy)pyrrolidine-1-carboxylate 
• 1237495-06-5 (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-((1S,2R)-2-(3-fluorophenyl)cyclopropylamino)ethoxy)pyrrolidine-1-carboxylate 
• 1424142-89-1 (3R,4R)-tert-butyl 3-((6-(benzyl(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-((tert-butoxycarbonyl)((1S,2R/1R,2S)-2-(3-fluorophenyl)cyclopropyl)amino)ethoxy)pyrrolidine-1-carboxylate 
• 1424142-91-5 (3R,4R)-tert-butyl 3-((6-(benzyl(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-((tert-butoxycarbonyl)((1S,2R)-2-(3-fluorophenyl)cyclopropyl)amino)ethoxy)pyrrolidine-1-carboxylate 
• 1237494-97-1 C₁₉H₂₂FNO₃ 
• 1237494-98-2 C₁₉H₂₂FNO₃ 
• 1424142-64-2 tert-Butyl 2-(3-fluorophenyl)cyclopropylcarbamate 
• 1422435-46-8 C₁₈H₁₃FN₄O 

Relevant academic research and scientific papers

PD(II)-CATALYZED ENANTIOSELECTIVE C-H ARYLATION OF FREE CARBOXYLIC ACIDS

The invention includes procedures for stereoselective β-arylation of carboxylic acids having a β-carbon atom. For example, stereoselective arylation procedures include the following reactions: (I)

Pd(II)-Catalyzed Enantioselective C(sp3)-H Arylation of Free Carboxylic Acids

A monoprotected aminoethyl amine chiral ligand based on an ethylenediamine backbone was developed to achieve Pd-catalyzed enantioselective C(sp3)-H arylation of cyclopropanecarboxylic and 2-aminoisobutyric acids without using exogenous directing groups. This new chiral catalyst affords new disconnection for preparing diverse chiral carboxylic acids from simple starting materials that are complementary to the various ring forming approaches.

Oxidative ring-opening of ferrocenylcyclopropylamines to N-ferrocenylmethyl β-hydroxyamides

The in situ reduction of ferrocenyl cyclopropylimines to the corresponding amines triggers a facile oxidative ring-opening to yield the formal four-electron oxidation products: N-ferrocenylmethyl β-hydroxyamides. This process is believed to proceed via generation of a ferrocinium ion in the presence of air, leading to facile formation of a distonic radical cation that is ultimately trapped by oxygen.

New Positive allosteric modulators of nicotinic acetylcholine receptor

The present invention relates to compounds useful in therapy, to compositions comprising said compounds, and to methods of treating diseases comprising administration of said compounds. The compounds referred to are positive allosteric modulators (PAMs) of the nicotinic acetylcholine α7 receptor.

Cyclopropyl- and methyl-containing inhibitors of neuronal nitric oxide synthase

Inhibitors of neuronal nitric oxide synthase have been proposed as therapeutics for the treatment of different types of neurological disorders. On the basis of a cis-3,4-pyrrolidine scaffold, a series of trans-cyclopropyl- and methyl-containing nNOS inhib

POTENT AND SELECTIVE NEURONAL NITRIC OXIDE SYNTHASE INHIBITORS WITH IMPROVED MEMBRANE PERMEABILITY

Compounds and related compositions and methods as can be used to inhibit neuronal nitric oxide synthase and as can be employed in the treatment of various neurodegenerative diseases.

Potent and Selective Neuronal Nitric Oxide Synthase Inhibitors with Improved Membrane Permeability

Compounds and related compositions and methods as can be used to inhibit neuronal nitric oxide synthase and as can be employed in the treatment of various neurodegenerative diseases.

Novel trans-2-aryl-cyclopropylamine analogues as potent and selective dipeptidyl peptidase IV inhibitors

A series of trans-2-aryl-cyclopropylamine derived compounds were synthesized and evaluated their biological activities against DPP-IV. The structure-activity relationships (SAR) led to the discovery of novel series of DPP-IV inhibitors, having IC50 values of 100 nM with excellent selectivity over the closely related enzymes, DPP8, DPP-II and FAP. The studies identified a potent and selective DPP-IV inhibitor 24b, which exhibited the ability to both significantly inhibit plasma DPP-IV activity in rats and improve glucose tolerance in lean mice and diet induced obese mice.

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.

5-HT2C RECEPTOR AGONISTS AS ANORECTIC AGENTS

This invention relates to compounds which modulate receptors of the 5-HT2 family of receptors, and particularly to compounds which modulate 5-HT2C receptors. Compounds of the invention include agonists and selective agonists for the 5-HT2C receptor. Compounds of the invention include selective agonists for the 5-HT2C receptor which exhibit significantly less or no agonist activity on the 5-HT2A receptor and/or the 5-HT2B receptor. Compounds of this invention are those of Formula I and pharmaceutically acceptable salts, esters and solvates (including hydrates) wherein variables are defined in the specification hereof.