6142-65-0

Usage

Molecular Weight

335.2

Structure

A cyclopropane ring (C3H5) attached to a phenyl group (C6H5) with a bromine atom (Br) in position 4, and a carboxylic acid group (COOH) attached to the cyclopropane ring.

+ Appearance

White or off-white crystalline solid

+ Melting Point

154-156°C

+ Boiling Point

Not readily available due to its stability

+ Solubility

Slightly soluble in water, soluble in organic solvents like ethanol, methanol, and acetone.

+ Reactivity

Can undergo reactions like esterification, amide formation, and halogenation.

+ Stability

Stable under normal temperature and pressure, but may decompose upon exposure to heat or strong oxidizing agents.

Biological Activity

+ Potential pharmacological and biological activities, making it an interesting target for drug discovery and medicinal chemistry research.

Applications

+ Synthesis of various pharmaceuticals and biologically active molecules
+ Building block in the preparation of diverse organic compounds
+ Versatile chemical with potential use in various applications.

Upstream product

• 53582-00-6 ethyl trans-2-(p-bromophenyl)-1-cyclopropanecarboxylate 
• 1200-07-3 trans-4-bromocinnamic acid 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 24393-53-1 ethyl (E)-3-(4-bromophenyl)-2-propenoate 
• 1122-91-4 4-bromo-benzaldehyde 
• 100115-96-6 4-Chlor-4-(4-brom-phenyl)-buttersaeureethylester 
• 1885-28-5 γ-(4-bromophenyl)-γ-butyrolactone 
• 134198-10-0 racemic 2-(4-bromo-phenyl)-trans-cyclopropanecarboxylic acid N-methoxy-N-methyl-amide 
• 589-87-7 1,4-bromoiodobenzene 
• 1759-53-1 cyclopropanecarboxylic acid 
• 2137065-16-6 (cis)-2-(4-bromophenyl)cyclopropanecarboxylic acid 

Downstream Products

• 1123620-89-2 (1S,2S)-2-(4-bromophenyl)cyclopropanecarboxylic acid 
• 31501-85-6 (R,R)-2-(4-bromophenyl)cyclopropanecarboxylic acid 
• 1418287-95-2 (±)-trans-O-tert-butyl-N-(2-(4-bromophenyl)cyclopropyl)carbamate 
• 90561-75-4 (1S,2R)-(+)-2-(4-bromophenyl)cyclopropyl-1-amine 

Relevant academic research and scientific papers

NOVEL LYSOPHOSPHATIDIC ACID DERIVATIVE

PROBLEM TO BE SOLVED: To provide a compound that specifically activates an LPA4 receptor, and a pharmaceutical composition containing the same. SOLUTION: This invention relates to a novel lysophosphatidic acid derivative that has an agonistic action on an LPA4 receptor and is useful for the prevention and/or treatment of a disease with angiodysplasia caused by the LPA4 receptor, or a disease associated with angiopathy, or symptoms associated therewith. This invention also relates to a pharmaceutical composition containing the lysophosphatidic acid derivative. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

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.

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.

Indazole-6-phenylcyclopropylcarboxylic Acids as Selective GPR120 Agonists with in Vivo Efficacy

GPR120 agonists have therapeutic potential for the treatment of diabetes, but few selective agonists have been reported. We identified an indazole-6-phenylcyclopropylcarboxylic acid series of GPR120 agonists and conducted SAR studies to optimize GPR120 potency. Furthermore, we identified a (S,S)-cyclopropylcarboxylic acid structural motif which gave selectivity against GPR40. Good oral exposure was obtained with some compounds displaying unexpected high CNS penetration. Increased MDCK efflux was utilized to identify compounds such as 33 with lower CNS penetration, and activity in oral glucose tolerance studies was demonstrated. Differential activity was observed in GPR120 null and wild-type mice indicating that this effect operates through a mechanism involving GPR120 agonism.

Structure activity relationship and modeling studies of inhibitors of lysine specific demethylase 1

Post-translational modifications of histone play important roles in gene transcription. Aberrant methylation of histone lysine sidechains have been often found in cancer. Lysine specific demethylase 1 (LSD1), which can demethylate histone H3 lysine 4 (H3K4) and other proteins, has recently been found to be a drug target for acute myeloid leukemia. To understand structure activity/selectivity relationships of LSD1 inhibitors, several series of cyclopropylamine and related compounds were synthesized and tested for their activities against LSD1 and related monoamine oxidase (MAO) A and B. Several cyclopropylamine containing compounds were found to be highly potent and selective inhibitors of LSD1. A novel series cyclopropylimine compounds also exhibited strong inhibitory activity against LSD1.Structure activity relationships (SAR) of these compounds are discussed. Docking studies were performed to provide possible binding models of a representative compound in LSD1 and MAO-A. Moreover, these modeling studies can rationalize the observed SARs and selectivity.

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.

(HETERO)ARYL CYCLOPROPYLAMINE COMPOUNDS AS LSD1 INHIBITORS

The invention relates to (hetero)aryl cyclopropylamine compounds, including particularly the compounds of formula I as described and defined herein, and their use in therapy, including, e.g., in the treatment or prevention of cancer, a neurological disease or condition, or a viral infection.

(HETERO)ARYL CYCLOPROPYLAMINE COMPOUNDS AS LSD1 INHIBITORS

The invention relates to (hetero)aryl cyclopropylamine compounds, including particularly the compounds of formula (I) as described and defined herein, and their use in therapy, including, e.g., in the treatment or prevention of cancer, a neurological disease or condition, or a viral infection.

ARYLCYCLOPROPYLAMINE BASED DEMETHYLASE INHIBITORS OF LSD1 AND THEIR MEDICAL USE

The invention relates to (hetero)aryl cyclopropylamine compounds, including particularly the compounds of formula (I) as described and defined herein, and their use in therapy, including, e.g., in the treatment or prevention of cancer, a neurological disease or condition, or a viral infection. Thus, in one specific aspect the invention relates to formulas (II), (III), (IV), (V), (VI), (VII), (VIII), (IX).