1199943-42-4

Basic information

• Product Name: (1-Propyl-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
• Synonyms: (1-Propyl-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
• CAS NO: 1199943-42-4
• Molecular Formula: C19H25NO
• Molecular Weight: 283.4079
• Mol File: 1199943-42-4.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.05
• CAS DataBase Reference: (1-Propyl-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone(CAS DataBase Reference)
• NIST Chemistry Reference: (1-Propyl-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone(1199943-42-4)
• EPA Substance Registry System: (1-Propyl-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone(1199943-42-4)

Safety Data

• Hazardous Substances Data: 1199943-42-4(Hazardous Substances Data)

Usage

General Description

(1-Propyl-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone, also known as PTI-125, is a chemical compound that has been studied for its potential therapeutic effects on neurodegenerative diseases such as Alzheimer's. It is a small molecule drug that has been shown to inhibit the toxic effects of amyloid beta peptides, which are believed to play a key role in the development and progression of Alzheimer's disease. PTI-125 has also been found to modulate the activity of certain enzymes in the brain, such as MMP-3 and MMP-9, which are associated with neuroinflammation and synaptic dysfunction. These actions suggest that PTI-125 has the potential to help protect and preserve cognitive function in individuals with neurodegenerative diseases, making it a promising candidate for future drug development and research.

Upstream product

• 24303-61-5 2,2,3,3-tetramethylcyclopropanecarbonyl chloride 
• 15641-58-4 2,2,3,3-tetramethylcyclopropane-1-carboxylic acid 
• 895152-66-6 (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone 
• 106-94-5 propyl bromide 

Relevant articles and documents

Development of high-affinity fluorinated ligands for cannabinoid subtype 2 receptor, and in vitro evaluation of a radioactive tracer for imaging

The development of neurodegenerative diseases is associated with cerebral inflammation, which activates resident immune cells of the central nervous system (CNS), namely microglial cells that show an up-regulation of the cannabinoid subtype 2 receptor (CB2R) expression. Therefore our work aimed to design and synthesize a radiotracer for the detection of CB2R expression by positron emission tomography (PET) allowing an early diagnosis of neurodegenerative diseases. For the development of such a PET tracer, N-alkyl-substituted indole-3-yl-tetramethylcyclopropylketones served as lead structures due to their high CB2R potency and selectivity, allowing radiolabeling on the N-alkyl chain. To this end, eight novel fluorinated N-alkyl-indole-3-yl-tetramethylcyclopropylketones were synthesized, investigated in radioligand binding studies, and structure-activity relationships were evaluated. The most promising candidate was (1-(4-fluoropropyl)-1H-indole-3-yl)(2,2,3,3-tetramethyl-cyclopropyl)methanone (Ki: 7.88 nM at the CB2R, 3430 nM at cannabinoid subtype 1 receptor (CB1R)). A precursor was synthesized, radiofluorinated with no-carrier-added [18F]F? by nucleophilic substitution of a tosyl group, and the resulting PET ligand was purified, all being performed on a fully automated synthesis module. The tracer was produced in 34 ± 6% radiochemical yield within 2 h and with molar activities of up to 1500 GBq/μmol. A first preclinical evaluation was carried out including determination of logP, metabolic stability by liver microsomes, and autoradiography. The novel PET tracer for imaging CB2R showed promising results warranting subsequent clinical evaluation.