604799-96-4

Usage

Uses

Used in Pharmaceutical Synthesis:
1-(2-BROMOPHENYL)CYCLOPROPANAMINE is used as a key intermediate in the synthesis of various pharmaceuticals for its unique cyclopropane and bromophenyl structures, which can be leveraged to create novel drug molecules with specific therapeutic properties.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, 1-(2-BROMOPHENYL)CYCLOPROPANAMINE serves as a building block for the creation of complex organic compounds, taking advantage of its reactive functional groups to form new chemical entities with potential applications in various industries.
Used in Medicinal Chemistry Research:
1-(2-BROMOPHENYL)CYCLOPROPANAMINE is utilized as a subject of study in medicinal chemistry to explore its potential biological activity. Researchers investigate its interactions with biological targets, which could lead to the discovery of new therapeutic agents or a better understanding of its pharmacological profile.

InChI:InChI=1/C9H10BrN/c10-8-4-2-1-3-7(8)9(11)5-6-9/h1-4H,5-6,11H2

Upstream product

• 2042-37-7 o-cyanobromobenzene 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 1021539-30-9 (4aS,5R)-5-(2-(1-aminocyclopropylphenyl)ethynyl)-1-(4-fluorophenyl)-4a-methyl-1,4,4a,5,6,7-hexahydrocyclopenta[f]indazol-5-ol 

Relevant academic research and scientific papers

Ligand Optimization by Improving Shape Complementarity at a Hepatitis C Virus RNA Target

Crystal structure analysis revealed key interactions of a 2-amino-benzimidazole viral translation inhibitor that captures an elongated conformation of an RNA switch target in the internal ribosome entry site (IRES) of hepatitis C virus (HCV). Here, we have designed and synthesized quinazoline derivatives with improved shape complementarity at the ligand binding site of the viral RNA target. A spiro-cyclopropyl modification aimed at filling a pocket in the back of the RNA binding site led to a 5-fold increase of ligand affinity while a slightly more voluminous dimethyl substitution at the same position did not improve binding. We demonstrate that precise shape complementarity based solely on hydrophobic interactions contributes significantly to ligand binding even at a hydrophilic RNA target site such as the HCV IRES conformational switch.

Exploiting Imine Photochemistry for Masked N-Centered Radical Reactivity

This report details the development of a masked N-centered radical strategy that harvests the energy of light to drive the conversion of cyclopropylimines to 1-aminonorbornanes. This process employs the N-centered radical character of a photoexcited imine to facilitate the homolytic fragmentation of the cyclopropane ring and the subsequent radical cyclization sequence that forms two new C?C bonds en route to the norbornane core. Achieving bond-forming reactivity as a function of the N-centered radical character of an excited state Schiff base is unique, requiring only violet light in this instance. This methodology operates in continuous flow, enhancing the potential to translate beyond the academic sector. The operational simplicity of this photochemical process and the structural novelty of the (hetero)aryl-fused 1-aminonorbornane products are anticipated to provide a valuable addition to discovery efforts in pharmaceutical and agrochemical industries.

2-[1-PHENYL-5-HYDROXY OR METHOXY-4ALPHA-METHYL-HEXAHYDROCLOPENTA[F]INDAZOL-5-YL]ETHYL PHENYL DERIVATIVES AS GLUCOCORTICOID RECEPTOR LIGANDS

The present invention is directed to 2- [l-phenyl-5 -hydroxy or methoxy-4alpha- methyl-hexahydrocyclopenta[f]indazol-5-yl]ethyl phenyl derivatives of formula I (I) as glucocorticoid receptor ligands useful for treating a variety of autoimmune and inflamma

A direct synthesis of 1-aryl- and 1-alkenylcyclopropylamines from aryl and alkenyl nitriles

The reaction of various aromatic nitriles with 1.1 equiv of Ti(Oi-Pr)4 and 2.2 equiv of EtMgBr followed by addition of a Lewis acid gave 1-aryl cyclopropylamines in 43-76% yields. Under similar conditions, conjugated alkene-nitriles afford 1-alkenylcyclopropylamines (42-65%).