1057343-95-9

Basic information

• Product Name: 5-Carboxy-2-Aminoadamantane
• Synonyms: 5-Carboxy-2-Aminoadamantane;4-Aminoadamantane-1-carboxylic acid;4-Aminotricyclo[3.3.1.13,7]decane-1-carboxylic acid;4-Aminoadamantane-1-Carbocylic acid
• CAS NO: 1057343-95-9
• Molecular Formula: C11H17NO2
• Molecular Weight: 195.25818
• Mol File: 1057343-95-9.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 343.8 °C at 760 mmHg
• Flash Point: 161.7 °C
• Appearance: /
• Density: 1.267
• CAS DataBase Reference: 5-Carboxy-2-Aminoadamantane(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Carboxy-2-Aminoadamantane(1057343-95-9)
• EPA Substance Registry System: 5-Carboxy-2-Aminoadamantane(1057343-95-9)

Safety Data

• Hazardous Substances Data: 1057343-95-9(Hazardous Substances Data)

Usage

Description

5-Carboxy-2-Aminoadamantane, also known as 2-aminoadamantane-5-carboxylic acid, is an organic compound derived from adamantane, a type of hydrocarbon. It features an aminoadamantane backbone with an additional carboxy functional group at the fifth carbon atom, which contributes to its solubility in various forms. This unique chemical structure makes it valuable for biochemical applications, particularly in medicinal chemistry and pharmaceutical studies. As a research chemical, 5-Carboxy-2-Aminoadamantane is widely used for multiple investigations and studies, although its potential in broader industrial applications remains largely unexplored. Its chemical formula is C12H17NO2.

Uses

Used in Medicinal Chemistry and Pharmaceutical Studies:
5-Carboxy-2-Aminoadamantane is used as a key intermediate in the synthesis of various pharmaceutical compounds and drug candidates. Its unique chemical structure allows for the development of novel therapeutic agents with improved pharmacological properties, such as enhanced solubility, bioavailability, and target specificity.
Used in Biochemical Research:
As a research chemical, 5-Carboxy-2-Aminoadamantane is employed in various biochemical investigations and studies. Its unique structure and properties make it a valuable tool for understanding the mechanisms of biological processes and for the development of new diagnostic and therapeutic approaches.
Used in Drug Design and Development:
5-Carboxy-2-Aminoadamantane is used as a building block in the design and development of new drugs. Its versatile chemical structure allows for the creation of innovative drug candidates with improved efficacy, safety, and pharmacokinetic profiles.
Used in Chemical Synthesis:
5-Carboxy-2-Aminoadamantane serves as a valuable starting material for the synthesis of a wide range of organic compounds. Its unique structure and reactivity make it an attractive candidate for the development of new chemical reactions and synthetic pathways.
While the potential of 5-Carboxy-2-Aminoadamantane in wider industrial applications is yet to be fully explored, its unique chemical properties and versatility in medicinal chemistry and pharmaceutical studies make it a promising compound for future research and development.

Upstream product

• 56674-87-4 4-oxoadamantane-1-carboxylic acid 
• 20098-14-0 chemantane 
• 20098-14-0 5-hydroxyadamantan-2-one 
• 700-58-3 adamantanone 

Downstream Products

• 898265-48-0 E-4-amino-adamantane-1-carboxylic acid methyl ester 
• 898265-48-0 (E)-methyl 4-aminoadamantane-1-carboxylate 
• 898265-48-0 Z-4-adamantamine-1-carboxylic acid methyl ester 
• 1422025-24-8 4-(2-methyl-2-(phenylsulfonamido)propanamido)adamantane-1-carboxyamide 
• 1422027-88-0 N-4-(2-(2-trifluoromethyl-N-propylphenylsulfonamido)-2-methylpropanamido)adamantane-1-carboxylic acid 
• 1422027-87-9 methyl 4-(2-(2-trifluoromethyl-N-propylphenylsulfonamido)-2-methylpropanamido)adamantane-1-carboxylate 

Relevant articles and documents

A convergent process for the preparation of adamantane 11-β-HSD-1 inhibitors

A convergent, scalable process was developed for the synthesis of adamantane 11-β-hydroxysteroid dehydrogenase-1 inhibitors E-4-(2-methyl-2-(4-(5-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl) propionylamino)adamantane-1-carboxylic acid (1) and E-4-(2-methyl-2-(4-(5- (trifluoromethyl)pyridin-2-yl)piperazin-1-yl)propionylamino)-adamantane-1- carboxamide (2) to rapidly deliver material for development. The process was high yielding and provided 1 in 52% overall yield over six total steps with a five-step longest linear sequence and 2 in 45% overall yield over seven total steps with a six-step longest linear sequence. A process to prepare active pharmaceutical ingredient (API) of >99% purity at the kilogram scale has been developed under tight delivery timelines.

Design of pyrazolo-pyrimidines as 11β-HSD1 inhibitors through optimisation of molecular electrostatic potential

The inhibition of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) is a potentially attractive mechanism for the treatment of obesity and other elements of the metabolic syndrome. A series of pyrazolo-pyrimidine inhibitors of this enzyme were identified from directed library synthesis. Knowledge of how these compounds bind to the enzyme and the key hydrogen-bonding interactions was used to design further compounds. The hydrogen-bond acceptor strength was calculated from the molecular electrostatic potential using quantum mechanical theory. Compounds were designed to modulate the acceptor strength, thus optimising the potency and other drug-like properties. Compounds with enhanced CNS penetration were designed through further modification of the electrostatic potential and the hydrogen-bond properties.

A COMPOUND FOR INHIBITING 11BETA-HYDROXY STEROID DEHYDROGENASE 1, AND A PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

Disclosed are a novel compound or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition including the same for inhibiting human 11-beta-hydroxy steroid dehydrogenase type 1 (11beta-HSD1). The disclosed compound and the pharmaceutical composition including the same for inhibiting human 11-beta-hydroxy steroid dehydrogenase type 1 (11beta-HSD1) are excellent in activity and solubility, and is more efficient in formulation and transfer.