15897-81-1

Usage

Uses

Used in Pharmaceutical Industry:
2-Adamantanecarboxylic acid is used as an intermediate in organic synthesis for the production of various pharmaceuticals. Its unique structure and properties make it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 2-Adamantanecarboxylic acid is utilized as a building block for the synthesis of agrochemicals, such as pesticides and herbicides. Its chemical properties allow for the creation of effective and targeted compounds for agricultural use.
Used in Antiviral and Antifungal Drug Development:
2-Adamantanecarboxylic acid is used as a key component in the development of antiviral and antifungal drugs. Its potential bioactivity against various pathogens makes it a promising candidate for the creation of new treatments in the medical field.
Used in Polymer and Coating Synthesis:
In the field of material science, 2-Adamantanecarboxylic acid is employed in the synthesis of polymers and coatings. Its chemical properties contribute to the development of innovative materials with improved properties, such as durability, stability, and resistance to environmental factors.
Used in Medical Research:
2-Adamantanecarboxylic acid has been studied for its anti-inflammatory and anti-tumor properties, making it a compound of interest in medical research. Its potential therapeutic effects on various conditions, including inflammation and cancer, highlight its importance in the development of new treatments and therapies.

InChI:InChI=1/C11H16O2/c12-11(13)10-8-2-6-1-7(4-8)5-9(10)3-6/h6-10H,1-5H2,(H,12,13)/p-1

Upstream product

• 35856-00-9 2-adamantanecarbonitrile 
• 22635-61-6 ((1r,3r,5r,7r)-adamantan-2-yl)methanol 
• 7314-85-4 2-adamantyl bromide 
• 124-38-9 carbon dioxide 
• 64-18-6 formic acid 
• 41736-95-2 spiro[adamantane-2,3'-diazirine] 
• 39750-93-1 adamantane-2-carbaldehyde 
• 15782-79-3 (+/-)-2-carbomethoxyadamantane-4,8-dione 
• 110-86-1 pyridine 
• 281-23-2 adamantane 
• 201230-82-2 carbon monoxide 
• 40079-92-3 2-adamantanecarbonyl chloride 
• 700-57-2 1-adamantanol 
• 412346-92-0 tert.-Butyl-epoxyadamantylidenacetat 

Downstream Products

• 314041-56-0 2-Benzoyl-adamantane-2-carboxylic acid (S)-2-methyl-butyl ester 
• 479415-86-6 Adamantane-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 314041-51-5 2-Benzoyl-adamantane-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 82679-52-5 1,1'-diadamantyl ketone 
• 26082-22-4 adamantan-2-ylacetic acid 
• 39750-93-1 adamantane-2-carbaldehyde 
• 3796-79-0 N-phenyl-1-adamantanecarboxamide 
• 107264-20-0 diphenylmethanone O-(adamantane-1-carbonyl) oxime 
• 102971-13-1 2-diphenylmethyladamantane 
• 7314-85-4 2-adamantyl bromide 
• 1073488-67-1 N'-(5-adamant-2-yl-6-chloropyridazin-3-yl)-2-methyl-2-phenylpropanehydrazide 
• 1073488-58-0 7-(adamant-2-yl)-6-chloro-(3-(2-phenyl)propan-2-yl)-[1,2,4]triazolo[4,3-b]pyridazine 

Relevant academic research and scientific papers

Koch-Haaf reaction of adamantanols in an acidtolerant hastelloy-made microreactor

The Koch-Haaf reaction of adamantanols was successfully carried out in a microflow system at room temperature. By combining an acid-tolerant hastelloy-made micromixer, a PTFE tube, and a hastelloy-made microextraction unit, a packaged reaction-toworkup system was developed. By means of the present system, the multigram scale synthesis of 1-adamantanecarboxylic acid was achieved in ca. one hour operation.

Discovery and metabolic stabilization of potent and selective 2-amino-N-(adamant-2-yl) acetamide 11β-hydroxysteroid dehydrogenase type 1 inhibitors

Starting from a rapidly metabolized adamantane 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor 22a, a series of E-5-hydroxy-2-adamantamine inhibitors, exemplified by 22d and (±)-22f, was discovered. Many of these compounds are potent inhibitors of 11β-HSD1 and are selective over 11β-HSD2 for multiple species (human, mouse, and rat), unlike other reported species-selective series. These compounds have good cellular potency and improved microsomal stability. Pharmacokinetic profiling in rodents indicated moderate to large volumes of distribution, short half-lives, and a pharmacokinetic species difference with the greatest exposure measured in rat with 22d. One hour postdose liver, adipose, and brain tissue 11β-HSD1 inhibition was confirmed with (±)-22f in a murine ex vivo assay. Although 5,7-disubstitued-2-adamantamines provided greater stability, a single, E-5-position, polar functional group afforded inhibitors with the best combination of stability, potency, and selectivity. These results indicate that adamantane metabolic stabilization sufficient to obtain short-acting, potent, and selective 11β-HSD1 inhibitors has been discovered.

Synthesis of Substituted Bridged Carboxylic Acids of the Adamantane Series

Abstract: A number of new 1,3,6- and 1,4,4-tri- and 1,3,6,6-tetrasubstituted polyfunctional derivatives were synthesized starting from bridged carboxylic acids of the adamantane series. The reactions were carried out in acidic media. A number of new amino acids were synthesized from 1-acetylamino- and 1,3-diacetylamino derivatives. The synthesized compounds can be considered as a molecular platform for the synthesis of new polymeric materials.

New chemical agents based on adamantane-monoterpene conjugates against orthopoxvirus infections

Currently, the spectrum of agents against orthopoxviruses, in particular smallpox, is very narrow. Despite the fact that smallpox is well controlled, there is, for many reasons, a real threat of epidemics associated with this or a similar virus. In order to search for new low molecular weight orthopoxvirus inhibitors, a series of amides combining adamantane and monoterpene moieties were synthesized using 1- and 2-adamantanecarboxylic acids as well as myrtenic, citronellic and camphorsulfonic acids as acid components. The produced compounds exhibited high activity against the vaccinia virus (an enveloped virus belonging to the poxvirus family), which was combined with low cytotoxicity. Some compounds had a selectivity index higher than that of the reference drug cidofovir; the highest SI = 1123 was exhibited by 1-adamantanecarboxylic acid amide containing the (-)-10-amino-2-pinene moiety. The produced compounds demonstrated inhibitory activity against other orthopoxviruses: cowpox virus (SI = 30-406) and ectromelia virus (mousepox virus, SI = 39-707). This journal is

INTRAESOPHAGEAL ADMINISTRATION OF TARGETED NITROXIDE AGENTS FOR PROTECTION AGAINST IONIZING IRRADIATION-INDUCED ESOPHAGITIS

Provided herein are compositions and related methods useful for prevention or mitigation of ionizing radiation-induced esophagitis. The compositions comprise compounds comprising a nitroxide-containing group attached to a mitochondria-targeting group. The

Ring-fused compound, pharmaceutical composition containing same and application of compound

The invention discloses a ring-fused compound, a preparation method thereof, pharmaceutical composition containing the compound and an application of the compound. A polycyclic compound (I) as well asan isomer, a prodrug, a stable isotopic derivative or pharmacologically acceptable salt of the compound (I) has the following structure. The polycyclic compound has good IDO1 and/or TDO2 inhibition functions, can effectively treat, relieve and/or prevent various diseases which are related with IDO1 and/or TDO2, such as cancer, virus infection, autoimmune diseases or the like.

FUSED-RING COMPOUNDS, PHARMACEUTICAL COMPOSITION AND USES THEREOF

This disclosure is related to a fused-ring compound of formula (I) and/or a pharmaceutically acceptable salt thereof, a pharmaceutical composition comprising the fused ring compound of formula (I) and/or a pharmaceutically acceptable salt thereof, preparation methods thereof, and use thereof in modulating activity of indoleamine 2, 3-dioxygenase (IDO) and/or tryptophan 2, 3-dioxygenase (TDO). This disclosure further provides methods of treating IDO and/or TDO-associated diseases, including cancer, viral infection and autoimmune diseases.

C H Bond Arylation of Diamondoids Catalyzed by Palladium(II) Acetate

We have developed an effective approach to 1,2-disubstituted diamondoids by palladium(II) acetate catalyzed functionalization of C H bond. Selective mono-arylation of the adamantane framework was achieved using picolylamide as a directing group in yields up to 87 %. Kinetic studies in combination with deuterium labeling experiments, competitive experiments and mass spectrometry contribute to the mechanistic understanding of the arylation process of alkanes with number of C H bonds neighboring the directing group. Triflic anhydride promoted cyclization of the directing group generates imidazo[1,5-a]pyridine derivatives. Acid-mediated removal of the directing group provides access to 2-aryl diamondoid carboxylic acids, which are common precursors for the synthesis of various bioactive compounds (drug candidates). (Figure presented.) .

Synthesis of analogs of the radiation mitigator JP4-039 and visualization of BODIPY derivatives in mitochondria

JP4-039 is a lead structure in a series of nitroxide conjugates that are capable of accumulating in mitochondria and scavenging reactive oxygen species (ROS). To explore structure-activity relationships (SAR), new analogs with variable nitroxide moieties were prepared. Furthermore, fluorophore-tagged analogs were synthesized and provided the opportunity for visualization in mitochondria. All analogs were tested for radioprotective and radiomitigative effects in 32Dcl3 cells.

Metal-free and copper-promoted single-pot hydrocarboxylation of cycloalkanes to carboxylic acids in aqueous medium

A simple and effective method for the transformation, under mild conditions and in aqueous medium, of various cycloalkanes (cyclopentane, cyclohexane, methylcyclohexane, cis- and trans-1,2dimethylcyclohexane, cycloheptane, cyclooctane and adamantane) into the corresponding cycloalkanecarboxylic acids bearing one more carbon atom, is achieved. This method is characterized by a singlepot, low-temperature hydrocarboxylation reaction of the cycloalkane with carbon monoxide, water and potassium peroxodisulfate in water/acetonitrile medium, proceeding either in the absence or in the presence of a metal promoter. The influence of various reaction parameters, such as type and amount of metal promoter, solvent composition, temperature, time, carbon monoxide pressure, oxidant and cycloalkane, is investigated, leading to an optimization of the cyclohexane and cyclopentane carboxylations. The highest efficiency is observed in the systems promoted by a tetracopper(II) triethanolaminate-de rived complex, which also shows different bond and stereoselectivity parameters (compared to the metalfree systems) in the carboxylations of methylcyclohexane and stereoisomeric 1,2-dimethylcyclohexanes. A free radical mechanism is proposed for the carboxylation of cyclohexane as a model substrate, involving the formation of an acyl radical, its oxidation and consequent hydroxylation by water. Relevant features of the present hydrocarboxylation method, besides the operation in aqueous medium, include the exceptional metal-free and acid-solvent-free reaction conditions, a rare hydroxylating role of water, substrate versatility, low temperatures (ca. 50°C) and a rather high efficiency (up to 72% carboxylic acid yields based on cycloalkane).