214557-89-8

Basic information

• Product Name: 3,5,7-Trifluoroadamantane-1-carboxylic acid
• Synonyms: 3,5,7-Trifluoroadamantane-1-carboxylic acid;3,5,7-trifluoro-Tricyclo[3.3.1.13,7]decane-1-carboxylic acid
• CAS NO: 214557-89-8
• Molecular Formula: C₁₁H₁₃F₃O₂
• Molecular Weight: 234
• Mol File: 214557-89-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 304.327 °C at 760 mmHg
• Flash Point: 137.853 °C
• Appearance: /
• Density: 1.41
• Storage Temp.: 2-8°C
• PKA: 3.11±0.70(Predicted)
• CAS DataBase Reference: 3,5,7-Trifluoroadamantane-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5,7-Trifluoroadamantane-1-carboxylic acid(214557-89-8)
• EPA Substance Registry System: 3,5,7-Trifluoroadamantane-1-carboxylic acid(214557-89-8)

Safety Data

• Hazardous Substances Data: 214557-89-8(Hazardous Substances Data)

Usage

General Description

3,5,7-Trifluoroadamantane-1-carboxylic acid is a chemical compound that belongs to the class of carboxylic acids. It is characterized by the presence of a adamantane core with three fluorine atoms attached at positions 3, 5, and 7. 3,5,7-Trifluoroadamantane-1-carboxylic acid has potential applications in the field of pharmaceuticals and materials science due to its unique molecular structure and properties. It can be used as a building block in the synthesis of various organic molecules and may possess biological activities that make it a promising candidate for drug development. Additionally, the presence of fluorine atoms can enhance the compound's chemical and physical properties, making it suitable for use in diverse applications.

Upstream product

• 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 
• 214557-86-5 methyl 3,5-difluoro-7-hydroxyadamantane-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 articles and documents

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.

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