52085-94-6

Usage

Uses

Used in Pharmaceutical Industry:
2,3-DIHYDRO-6-FLUORO-1H-INDEN-1-OL is used as a key intermediate for the development of new drugs, leveraging its distinctive structural features and reactivity to contribute to the creation of innovative medicinal compounds.
Used in Organic Chemistry:
In the realm of organic chemistry, 2,3-DIHYDRO-6-FLUORO-1H-INDEN-1-OL serves as a building block, particularly in the synthesis of heterocyclic compounds, which are essential in a variety of chemical and pharmaceutical applications.
Used in Medicinal and Research Purposes:
2,3-DIHYDRO-6-FLUORO-1H-INDEN-1-OL is also utilized as an intermediate in the production of various compounds that are vital for both medicinal applications and scientific research, further expanding its significance in the field of chemistry and drug development.

Upstream product

• 1481-32-9 6-fluoroindan-1-one 
• 459-32-5 4-fluorocinnamic acid 
• 459-31-4 3-(4-fluorophenyl)propanoic acid 
• 772-70-3 3-(4-fluorophenyl)propanoyl chloride 
• 459-57-4 4-fluorobenzaldehyde 

Downstream Products

• 52031-15-9 5-fluoro-1H-indene 
• 1075-12-3 7-fluoroisoquinoline 
• 939760-59-5 rac-cis-(1a,6a)-3-fluoro-6,6a-dihydro-1aH-1-oxacyclopropa[a]indene 

Relevant academic research and scientific papers

Asymmetric Magnesium-Catalyzed Hydroboration by Metal-Ligand Cooperative Catalysis

Asymmetric catalysis with readily available, cheap, and non-toxic alkaline earth metal catalysts represents a sustainable alternative to conventional synthesis methodologies. In this context, we describe the development of a first MgII-catalyzed enantioselective hydroboration providing the products with excellent yields and enantioselectivities. NMR spectroscopy studies and DFT calculations provide insights into the reaction mechanism and the origin of the enantioselectivity which can be explained by a metal-ligand cooperative catalysis pathway involving a non-innocent ligand.

SPIROCYCLIC COMPOUNDS AS MODULATORS OF INDOLEAMINE 2,3-DIOXYGENASE

The present invention relates to novel spirocyclic compounds of formulas (1) and (2) which act as modulators of indoleamine 2,3-dioxygenase (ID01) and to the use of said compounds in the prophylaxis and/or treatment of diseases or conditions mediated by indoleamine 2,3-dioxygenase. The invention further relates to pharmaceutical compositions comprising the novel compounds.

Synthesis of Indole-Dihydroisoquinoline Sulfonyl Ureas via Three-Component Reactions

Isoquinolines activated with sulfamoyl chlorides were reacted with indoles in a 3-component reaction to generate a library of dihydroisoquinoline derivatives. Using a differential protecting group strategy, products could be further derivatised. Synthesis of isoquinoline starting materials using several different methods is also described.

Discovery and Optimization of 1-Phenoxy-2-aminoindanes as Potent, Selective, and Orally Bioavailable Inhibitors of the Na+/H+ Exchanger Type 3 (NHE3)

The design, synthesis, and structure-activity relationship of 1-phenoxy-2-aminoindanes as inhibitors of the Na+/H+ exchanger type 3 (NHE3) are described based on a hit from high-throughput screening (HTS). The chemical optimization resulted in the discovery of potent, selective, and orally bioavailable NHE3 inhibitors with 13d as best compound, showing high in vitro permeability and lacking CYP2D6 inhibition as main optimization parameters. Aligning 1-phenoxy-2-aminoindanes onto the X-ray structure of 13d then provided 3D-QSAR models for NHE3 inhibition capturing guidelines for optimization. These models showed good correlation coefficients and allowed for activity estimation. In silico ADMET models for Caco-2 permeability and CYP2D6 inhibition were also successfully applied for this series. Moreover, docking into the CYP2D6 X-ray structure provided a reliable alignment for 3D-QSAR models. Finally 13d, renamed as SAR197, was characterized in vitro and by in vivo pharmacokinetic (PK) and pharmacological studies to unveil its potential for reduction of obstructive sleep apneas.

SEROTONIN RECEPTOR MODULATORS

The biphenyic compounds of formula (I) are serotonin modulators useful in the treatment of serotonin-mediated diseases.

2,4-DIAMINOQUINAZOLINES FOR SPINAL MUSCULAR ATROPHY

2,4-Diaminoquinazolines of formulae I-IV and VI (I, II, III, IV and VI) are useful for treating spinal muscular atrophy (SMA).