214557-89-8

Usage

Uses

Used in Pharmaceutical Industry:
3,5,7-Trifluoroadamantane-1-carboxylic acid is used as a key intermediate in the synthesis of pharmaceutical compounds for its potential biological activities. The presence of fluorine atoms can enhance the compound's pharmacokinetic and pharmacodynamic properties, improving drug efficacy and selectivity.
Used in Materials Science:
3,5,7-Trifluoroadamantane-1-carboxylic acid is utilized as a component in the development of advanced materials due to its unique molecular structure and properties. The fluorine atoms can impart enhanced chemical and physical characteristics, such as increased stability and reactivity, making it suitable for a wide range of applications in materials science.
Used in Organic Synthesis:
3,5,7-Trifluoroadamantane-1-carboxylic acid serves as a valuable building block in the synthesis of various organic molecules. Its adamantane core and fluorine substituents offer opportunities for the creation of novel compounds with tailored properties for specific applications in chemistry and related fields.

Upstream product

• 214557-86-5 methyl 3,5-difluoro-7-hydroxyadamantane-1-carboxylate 
• 828-51-3 1-Adamantanecarboxylic acid 
• 1426-93-3 methyl 3-fluoroadamantane-1-carboxylate 
• 214557-81-0 methyl 3,5-difluoroadamantane-1-carboxylate 
• 214557-80-9 methyl 3-fluoro-5-hydroxyadamantane-1-carboxylate 
• 68435-07-4 1-methoxycarbonyl-3-hydroxyadamantane 
• 711-01-3 methyl adamantane-1-carboxylate 
• 214557-84-3 methyl 3,5,7-trifluoroadamantane-1-carboxylate 

Downstream Products

• 214557-91-2 benzyl 3,5,7-trifluoroadamantane-1-carbamate 

Relevant academic research and scientific papers

ADAMANTANYL-SUBSTITUTED BENZAMIDE COMPOUNDS AND THEIR USE AS P2X7 RECEPTOR ANTAGONISTS

The present invention relates to adamantanyl-substituted benzamide compounds and their use as antagonists of the P2X7 purinoreceptor. The invention further relates to methods for the treatment of disease and conditions associated with the P2X7 purinoreceptor.

Electrochemical C(sp 3)-H Fluorination

A simple and robust method for electrochemical alkyl C-H fluorination is presented. Using a simple nitrate additive, a widely available fluorine source (Selectfluor), and carbon-based electrodes, a wide variety of activated and unactivated C-H bonds are converted into their C-F congeners. The scalability of the reaction is also demonstrated with a 100 gram preparation of fluorovaline.

Pharmacological Evaluation of Novel Bioisosteres of an Adamantanyl Benzamide P2X7 Receptor Antagonist

Adamantanyl benzamide 1 was identified as a potent P2X7R antagonist but failed to progress further due to poor metabolic stability. We describe the synthesis and SAR of a series of bioisosteres of benzamide 1 to explore improvements in the pharmacological properties of this lead. Initial efforts investigated a series of heteroaromatic bioisosteres, which demonstrated improved physicochemical properties but reduced P2X7R antagonism. Installation of bioisosteric fluorine on the adamantane bridgeheads was well tolerated and led to a series of bioisosteres with improved physicochemical properties and metabolic stability. Trifluorinated benzamide 34 demonstrated optimal physicochemical parameters, superior metabolic stability (ten times longer than lead benzamide 1), and an improved physicokinetic profile and proved effective in the presence of several known P2X7R polymorphisms.

Fluoro-substituted adamantane derivatives

The invention relates to fluoro-substituted adamantane derivatives of the formula and to pharmaceutically acceptable salts thereof, wherein R1, R2, R3, and R4 are as defined herein. The invention also relates to methods of treating neurological disorders, such as memory loss and Parkinson's disease, and bacterial and viral infections, through administration of a therapeutically effective amount of a compound of formula I. The invention also relates to a method of increasing the metabolic stability of an adamantane-containing pharmaceutical compound by incorporating a fluoro substituent on at least one bridge-head carbon of the adamantyl group of said adamantane-containing pharmaceutical compound

Preparation of fluoroadamantane acids and amines: Impact of bridgehead fluorine substitution on the solution- and solid-state properties of functionalized adamantanes

Functionalized adamantanes are utilized as medicinal therapeutics and a practical route to novel bridgehead fluorinated adamantylamines and acids including fully fluorinated 3,5,7-tri-fluoroadamantane-1-carboxylic acid 1 and 3,5,7-trifluoroadamantane-1-am

Fluoro-substituted adamantane derivatives

The invention relates to fluoro-substituted adamantane derivatives of the formula and to pharmaceutically acceptable salts thereof, wherein R1, R2, R3, and R4are as defined herein. The invention also relates to methods of treating neurological disorders, such as memory loss and Parkinson's disease, and bacterial and viral infections, through administration of a therapeutically effective amount of a compound of formula I. The invention also relates to a method of increasing the metabolic stability of an adamantane-containing pharmaceutical compound by incorporating a fluoro substituent on at least one bridge-head carbon of the adamantyl group of said adamantane-containing pharmaceutical compound.