1228092-84-9

Usage

Uses

Used in Medicinal Chemistry:
(1R,2RS)-(-)-2-(4-bromophenyl)cyclopropyl-1-amine hydrochloride is used as a target for drug development due to its unique structure and chirality, which may offer novel interactions with biological targets and contribute to the creation of new therapeutic agents.
Used in Research and Development:
In the field of biological research, (1R,2RS)-(-)-2-(4-bromophenyl)cyclopropyl-1-amine hydrochloride serves as a valuable research tool. Its specific stereochemistry allows scientists to study its effects on various biological systems, potentially leading to a better understanding of its role in physiological processes and the discovery of new therapeutic applications.
Used in Pharmaceutical Industry:
(1R,2RS)-(-)-2-(4-bromophenyl)cyclopropyl-1-amine hydrochloride is utilized in the pharmaceutical industry for the development of new drugs. Its unique molecular structure and properties may provide advantages in drug design, such as selectivity for specific targets, improved pharmacokinetics, and enhanced efficacy in treating various diseases.
Used in Drug Synthesis:
As a building block in organic synthesis, (1R,2RS)-(-)-2-(4-bromophenyl)cyclopropyl-1-amine hydrochloride can be employed in the synthesis of more complex pharmaceutical compounds. Its presence in these molecules may impart specific biological activities or improve the overall performance of the drug candidates.
Used in Chiral Compound Analysis:
(1R,2RS)-(-)-2-(4-bromophenyl)cyclopropyl-1-amine hydrochloride is also used in the analysis and study of chiral compounds. Understanding the behavior and properties of chiral molecules is crucial in the development of enantiomerically pure drugs, which can have significant implications for the safety and efficacy of pharmaceutical products.

Upstream product

• 31501-85-6 (R,R)-2-(4-bromophenyl)cyclopropanecarboxylic acid 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 1231764-59-2 tert-butyl trans-2-(4-bromophenyl)cyclopropane-1-carboxylate 
• 907196-12-7 (1R,2S)-tert-butyl 2-(4-bromophenyl)cyclopropylcarbamate 

Downstream Products

• 1418287-95-2 (±)-trans-O-tert-butyl-N-(2-(4-bromophenyl)cyclopropyl)carbamate 
• 1357298-75-9 trans-4'-(2-aminocyclopropyl)-(1,1'-biphenyl)-3-ol hydrochloride 

Relevant academic research and scientific papers

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.

Biochemical, structural, and biological evaluation of tranylcypromine derivatives as inhibitors of histone demethylases LSD1 and LSD2

LSD1 and LSD2 histone demethylases are implicated in a number of physiological and pathological processes, ranging from tumorigenesis to herpes virus infection. A comprehensive structural, biochemical, and cellular study is presented here to probe the potential of these enzymes for epigenetic therapies. This approach employs tranylcypromine as a chemical scaffold for the design of novel demethylase inhibitors. This drug is a clinically validated antidepressant known to target monoamine oxidases A and B. These two flavoenzymes are structurally related to LSD1 and LSD2. Mechanistic and crystallographic studies of tranylcypromine inhibition reveal a lack of selectivity and differing covalent modifications of the FAD cofactor depending on the enantiomeric form. These findings are pharmacologically relevant, since tranylcypromine is currently administered as a racemic mixture. A large set of tranylcypromine analogues were synthesized and screened for inhibitory activities. We found that the common evolutionary origin of LSD and MAO enzymes, despite their unrelated functions and substrate specificities, is reflected in related ligand-binding properties. A few compounds with partial enzyme selectivity were identified. The biological activity of one of these new inhibitors was evaluated with a cellular model of acute promyelocytic leukemia chosen since its pathogenesis includes aberrant activities of several chromatin modifiers. Marked effects on cell differentiation and an unprecedented synergistic activity with antileukemia drugs were observed. These data demonstrate that these LSD1/2 inhibitors are of potential relevance for the treatment of promyelocytic leukemia and, more generally, as tools to alter chromatin state with promise of a block of tumor progression.