75375-89-2

Basic information

• Product Name: 4-Amino-tricyclo[3.3.1.13,7]decan-1-ol
• Synonyms: 1-Hydroxy-4-aminoadamantane;4-Amino-tricyclo[3.3.1.13,7]decan-1-ol;4-aminoadamantan-1-ol(SALTDATA: HCl)
• CAS NO: 75375-89-2
• Molecular Formula: C₁₀H₁₇NO
• Molecular Weight: 167.24808
• Mol File: 75375-89-2.mol

Chemical Properties

• Melting Point: 258-260 °C(Solv: toluene (108-88-3))
• Boiling Point: 275.6±33.0 °C(Predicted)
• Appearance: /
• Density: 1.205
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 15.14±0.40(Predicted)
• CAS DataBase Reference: 4-Amino-tricyclo[3.3.1.13,7]decan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-tricyclo[3.3.1.13,7]decan-1-ol(75375-89-2)
• EPA Substance Registry System: 4-Amino-tricyclo[3.3.1.13,7]decan-1-ol(75375-89-2)

Safety Data

• Hazardous Substances Data: 75375-89-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Amino-tricyclo[3.3.1.13,7]decan-1-ol is utilized as a key intermediate in organic synthesis for its ability to participate in a variety of chemical reactions due to its amino and hydroxyl functional groups. Its tricyclic structure provides a rigid and unique scaffold for the development of complex organic molecules.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 4-Amino-tricyclo[3.3.1.13,7]decan-1-ol serves as a promising candidate for the development of new drugs. Its structural features may allow it to interact with biological targets in novel ways, potentially leading to the creation of medicines with improved efficacy and selectivity.
Used in Chemical Research:
4-Amino-tricyclo[3.3.1.13,7]decan-1-ol is employed as a subject of study in chemical research to understand its reactivity, stability, and the influence of its tricyclic structure on molecular interactions. This research can provide insights into new reaction mechanisms and the design of advanced materials and compounds.

Upstream product

• 13074-39-0 N-(2-adamantyl)amine 
• 20098-14-0 chemantane 
• 20098-19-5 1-hydroxy-4-aminoadamantane hydrochloride 
• 353241-69-7 C₁₂H₁₈N₂O₄ 
• 20098-18-4 5-hydroxy-adamantan-2-one oxime 
• 10523-68-9 adamantan-2-amine hydrochloride 

Downstream Products

• 923595-80-6 benzyl (E-5-hydroxyadamantan-2-yl)carbamate 

Relevant articles and documents

Discovery and Optimization of Allosteric Inhibitors of Mutant Isocitrate Dehydrogenase 1 (R132H IDH1) Displaying Activity in Human Acute Myeloid Leukemia Cells

A collaborative high throughput screen of 1.35 million compounds against mutant (R132H) isocitrate dehydrogenase IDH1 led to the identification of a novel series of inhibitors. Elucidation of the bound ligand crystal structure showed that the inhibitors exhibited a novel binding mode in a previously identified allosteric site of IDH1 (R132H). This information guided the optimization of the series yielding submicromolar enzyme inhibitors with promising cellular activity. Encouragingly, one compound from this series was found to induce myeloid differentiation in primary human IDH1 R132H AML cells in vitro.

INHIBITORS OF 11BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1

This invention relates to novel compounds of the Formula (I*), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof which are useful for the therapeutic treatment of diseases associated with the modulation or inhibition of 11

The development and SAR of pyrrolidine carboxamide 11β-HSD1 inhibitors

The design and development of a series of highly selective pyrrolidine carboxamide 11β-HSD1 inhibitors are described. These compounds including PF-877423 demonstrated potent in vitro activity against both human and mouse 11β-HSD1 enzymes. In an in vivo assay, PF-877423 inhibited the conversion of cortisone to cortisol. Structure guided optimization effort yielded potent and stable 11β-HSD1 selective inhibitor 42.

N-ADAMANTYL BENZAMIDES AS INHIBITORS OF 11-BETA-HYDROXYSTEROID DEHYDROGENASE

Novel substituted benzamide based inhibitors, their use in therapy, pharmaceutical compositions comprising the compounds, the use of said compounds in the manufacture of medicaments, and therapeutic methods comprising the administration of said compounds

NOVEL COMPOUNDS

Novel substituted benzamide based inhibitors, their use in therapy, pharmaceutical compositions comprising the compounds, the use of said compounds in the manufacture of medicaments, and therapeutic methods comprising the administration of said compounds are described. The present compounds modulate the activity of 11β-hydroxysteroid dehydrogenase type 1 (11βHSD1) and are accordingly useful in the treatment of diseases in which such a modulation is beneficial, such as the metabolic syndrome.

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.

Discovery of adamantane ethers as inhibitors of 11β-HSD-1: Synthesis and biological evaluation

A novel class of adamantane ethers 11β-hydroxysteroid hydrogenase type I inhibitors has been discovered. These compounds have excellent HSD-1 potency and selectivity against HSD-2. The structure-activity relationships, selectivity, metabolism, PK, ex vivo

Adamantyl-pyrazole carboxamides as inhibitors of 11B-hydroxysteroid dehydrogenase

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, type II diabetes mellitus and metabolic syndrome.

2-Adamantylurea derivatives as selective 11B-HSD1 inhibitors

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Thiazoles as inhibitors of 11B-hydroxysteroid dehydrogenase

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, type II diabetes mellitus and metabolic syndrome.