879324-64-8

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
2-(4-FLUOROPHENYL)CYCLOPROPANECARBOXYLIC ACID is used as a chemical intermediate for the synthesis of pharmaceutical compounds due to its unique structural features and potential to interact with biological systems.
Used in Organic Chemistry:
2-(4-FLUOROPHENYL)CYCLOPROPANECARBOXYLIC ACID is used as a building block for the synthesis of other chemical compounds, contributing to the development of new organic molecules and materials.

Upstream product

• 893751-08-1 trans-methyl 2-(4-fluorophenyl)cyclopropanecarboxylate 
• 623-73-4 diazoacetic acid ethyl ester 
• 405-99-2 para-fluorostyrene 
• 301861-15-4 (+/-)-trans-2-(4-fluorophenyl)cyclopropanecarbonitrile 
• 75-47-8 iodoform 
• 459-32-5 (E)-4-fluorocinnamic acid 
• 459-57-4 4-fluorobenzaldehyde 
• 243665-10-3 (E)-3-(4-fluorophenyl)-N-methoxy-N-methylacrylamide 
• 352-34-1 4-fluoro-1-iodobenzene 
• 96426-60-7 methyl (2E)-3-(4-fluorophenyl)-2-propenoate 
• 70461-58-4 trans-2-(4-fluorophenyl)cyclopropane carboxylic acid ethyl ester 
• 136265-10-6 ethyl 4-fluorocinnamate 
• 1774-47-6 trimethylsulfoxonium iodide 
• 301861-15-4 trans-2-(4-fluorophenyl)cyclopropane-1-carbonitrile 

Downstream Products

• 1414775-42-0 (1R,2R)-2-(4-fluorophenyl)cyclopropanecarboxylic acid [(R)-cyclopropyl-(3-ethanesulfonylphenyl)methyl](6-trifluoromethylpyridin-3-ylmethyl)amide 
• 1414775-44-2 (1R,2R)-2-(4-fluorophenyl)cyclopropanecarboxylic acid [(S)-cyclopropyl-(3-ethanesulfonylphenyl)methyl](6-trifluoromethylpyridin-3-ylmethyl)amide 
• 161711-27-9 (1R,2R)-2-(4-fluorophenyl)cyclopropanecarboxylic acid 
• 1609030-98-9 2-(4-fluorophenyl)-N-(2-(2-methyl-1H-indol-1-yl)ethyl)cyclopropane-1-carboxamide 
• 1314323-96-0 (1R,2S)-tert-butyl 2-(4-fluorophenyl)cyclopropylcarbamate 
• 113516-71-5 (1R,2S)-2-(4-fluorophenyl)cyclopropan-1-amine 
• 515179-19-8 (+)-(1S,2S)-2-(4-fluorophenyl)cyclopropanecarboxylic acid 

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)

PdII-Catalyzed Enantioselective C(sp3)?H Activation/Cross-Coupling Reactions of Free Carboxylic Acids

PdII-catalyzed enantioselective C(sp3)?H cross-coupling of free carboxylic acids with organoborons has been realized using either mono-protected amino acid (MPAA) ligands or mono-protected aminoethyl amine (MPAAM) ligands. A diverse range of aryl- and vinyl-boron reagents can be used as coupling partners to provide chiral carboxylic acids. This reaction provides an alternative approach to the enantioselective synthesis of cyclopropanecarboxylic acids and cyclobutanecarboxylic acids containing α-chiral tertiary and quaternary stereocenters. The utility of this reaction was further demonstrated by converting the carboxylic acid into cyclopropyl amine without loss of optical activity.

Co(II)-salen catalyzed stereoselective cyclopropanation of fluorinated styrenes

Three cis-selective Co(II)-salen complexes have been developed for the asymmetric cyclopropanation of para-fluorinated styrenes with ethyl diazoacetate. Increasing the steric reach of the C2-symmetric ligand side chains improved the enantiomeric ratio of the reaction from 28:1 to 66:1. The methodology was exemplified by the gram-scale synthesis of a lead compound for the treatment of castration-resistant prostate cancer (CRPC), as well as a structurally related analog.

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.

Synthesis and in vitro evaluation of novel N-cycloalkylcarbamates as potential cholinesterase inhibitors

Abstract: This present paper describes the preparation and characterization of a series of O-substituted N-cycloalkylcarbamate derivatives. These compounds were tested as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). All studied carbamates exhibited moderate inhibitory activity of both cholinesterases with values of IC50 in the range of 36.1–78.6?μM for AChE and 9.8–215.4?μM for BChE, respectively. These values are comparable with those values of inhibition obtained with the established drug rivastigmine. The cytotoxicity of all carbamates was evaluated using standard in vitro test with Jurkat cells. Many of the studied carbamates can be considered as promising compounds for potential medicinal applications with regard to their inhibitory activity as well as negligible cytotoxicity.

KDM1A INHIBITORS FOR THE TREATMENT OF DISEASE

Disclosed herein are new compounds and compositions and their application as pharmaceuticals for the treatment of diseases. Methods of inhibition of KDMIA, and methods of increasing gamma globin gene expression in a human or animal subject are also provided for the treatment diseases such as sickle cell disease.

Silver-promoted, palladium-catalyzed direct arylation of cyclopropanes: Facile access to spiro 3,3′-cyclopropyl oxindoles

The Pd-catalyzed, Ag(I)-mediated intramolecular direct arylation of cyclopropane C-H bonds is described. Various spiro 3,3′-cyclopropyl oxindoles can be obtained in good to excellent yields from easily accessible 2-bromoanilides. The kinetic isotope effect was determined and epimerization studies were conducted, suggesting that the formation of a putative Pd-enolate is not operative and that the reaction proceeds via a C-H arylation pathway.

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.

AMINE DERIVATIVES AS POTASSIUM CHANNEL BLOCKERS

The present invention relates to compounds useful in the modulation of potassium channel activity in cells, in particular the activity of Kv1.3 channels found in T cells. The invention also relates to the use of these compounds in the treatment or prevention of autoimmune and inflammatory diseases, including multiple sclerosis, pharmaceutical compositions containing these compounds and methods for their preparation.

Enantioselective synthesis of tranylcypromine analogues as lysine demethylase (LSD1) inhibitors

Asymmetric cyclopropanation of styrenes by tert-butyl diazoacetate followed by ester hydrolysis and Curtius rearrangement gave a series of tranylcypromine analogues as single enantiomers. The o,- m- and p-bromo analogues were all more active than tranylcypromine in a LSD1 enzyme assay. The m- and p-bromo analogues were micromolar growth inhibitors of the LNCaP prostate cancer cell line as were the corresponding biphenyl analogues prepared from the bromide by Suzuki crosscoupling.