62058-03-1

Basic information

• Product Name: Trans-4-Amino-1-hydroxy-adamantane
• Synonyms: Trans-4-Amino-1-hydroxy-adamantane;Trans-4-Aminoadamantan-1-ol;4-Amino-1-hydroxy-adamantane;(1R,3S,4S,5S,7S)-rel-4-AMinoadaMantan-1-ol
• CAS NO: 62058-03-1
• Molecular Formula: C₁₀H₁₇NO
• Molecular Weight: 167.24808
• EINECS: 229-842-9
• Mol File: 62058-03-1.mol

Chemical Properties

• Melting Point: 230-235℃
• Boiling Point: 276℃
• Flash Point: 120℃
• Appearance: /
• Density: 1.205
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 15.14±0.40(Predicted)
• CAS DataBase Reference: Trans-4-Amino-1-hydroxy-adamantane(CAS DataBase Reference)
• NIST Chemistry Reference: Trans-4-Amino-1-hydroxy-adamantane(62058-03-1)
• EPA Substance Registry System: Trans-4-Amino-1-hydroxy-adamantane(62058-03-1)

Safety Data

• Hazardous Substances Data: 62058-03-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Trans-4-Amino-1-hydroxy-adamantane is used as a potential therapeutic agent for the treatment of neurodegenerative diseases such as Parkinson's and Alzheimer's. Its unique structure and properties have shown promise in research studies, making it a candidate for further development and clinical trials.
Used in Antiviral Applications:
Trans-4-Amino-1-hydroxy-adamantane is used as an antiviral agent, where its specific properties have demonstrated the ability to inhibit viral replication and reduce the severity of viral infections. This application is particularly relevant in the ongoing search for effective treatments against various viral diseases.
Used in Anticancer Applications:
In the field of oncology, Trans-4-Amino-1-hydroxy-adamantane is used as a potential anticancer agent. Its pharmacological properties have shown the capacity to target and inhibit the growth of cancer cells, offering a new avenue for cancer treatment and management.
While the provided materials do not specify different industries for the uses of Trans-4-Amino-1-hydroxy-adamantane, the applications mentioned are primarily within the pharmaceutical and medical fields, given the compound's potential therapeutic properties. Further research and development are necessary to fully understand and harness the compound's capabilities in these areas.

Upstream product

• 13074-39-0 N-(2-adamantyl)amine 
• 62058-13-3 4-aminoadamantan-1-ol 

Relevant articles and documents

Adamantyl analogues of paracetamol as potent analgesic drugs via inhibition of TRPA1

Paracetamol also known as acetaminophen, is a widely used analgesic and antipyretic agent. We report the synthesis and biological evaluation of adamantyl analogues of paracetamol with important analgesic properties. The mechanism of nociception of compoun

Discovery and structural characterization of peficitinib (ASP015K) as a novel and potent JAK inhibitor

Janus kinases (JAKs) are considered promising targets for the treatment of autoimmune diseases including rheumatoid arthritis (RA) due to their important role in multiple cytokine receptor signaling pathways. Recently, several JAK inhibitors have been developed for the treatment of RA. Here, we describe the identification of the novel orally bioavailable JAK inhibitor 18, peficitinib (also known as ASP015K), which showed moderate selectivity for JAK3 over JAK1, JAK2, and TYK2 in enzyme assays. Chemical modification at the C4-position of lead compound 5 led to a large increase in JAK inhibitory activity and metabolic stability in liver microsomes. Furthermore, we determined the crystal structures of JAK1, JAK2, JAK3, and TYK2 in a complex with peficitinib, and revealed that the 1H-pyrrolo[2,3–b]pyridine-5-carboxamide scaffold of peficitinib forms triple hydrogen bonds with the hinge region. Interestingly, the binding modes of peficitinib in the ATP-binding pockets differed among JAK1, JAK2, JAK3, and TYK2. WaterMap analysis of the crystal structures suggests that unfavorable water molecules are the likely reason for the difference in orientation of the 1H-pyrrolo[2,3-b]pyridine-5-carboxamide scaffold to the hinge region among JAKs.

Optimization of brain penetrant 11β-hydroxysteroid dehydrogenase type i inhibitors and in vivo testing in diet-induced obese mice

11β-Hydroxysteroid dehydrogenase type 1 (11β-HSD1) has been widely considered by the pharmaceutical industry as a target to treat metabolic syndrome in type II diabetics. We hypothesized that central nervous system (CNS) penetration might be required to see efficacy. Starting from a previously reported pyrimidine compound, we removed hydrogen-bond donors to yield 3, which had modest CNS penetration. More significant progress was achieved by changing the core to give 40, which combines good potency and CNS penetration. Compound 40 was dosed to diet-induced obese (DIO) mice and gave excellent target engagement in the liver and high free exposures of drug, both peripherally and in the CNS. However, no body weight reduction or effects on glucose or insulin were observed in this model. Similar data were obtained with a structurally diverse thiazole compound 51. This work casts doubt on the hypothesis that localized tissue modulation of 11β-HSD1 activity alleviates metabolic syndrome.

Selective hydroxylation of adamantane and its derivatives

A general method was developed for hydroxylation into the nodal position of adamantane and its 1- and 2-substituted derivatives employing systems H 2O-CBr4 (BrCCl3, CCl4) in the presence of complexes of Pd, Ni, Ru, Co, Mo, W, and Fe. The oxidants in the systems are hypochlorous (HOCl) or hypobromous (HOBr) acids generated from water and halomethanes under the reaction conditions.

PROCESS FOR PRODUCTION OF HYDROXYADAMANTANEAMINE

Disclosed is a process for producing 1-hydroxy-4-aminoadamantane.

Hyperconjugative control by remote substituents of diastereoselectivity in the oxygenation of hydrocarbons

(figure presented) The oxidation of 2-substituted adamantanes (2) with TFDO (1) is reported. The data show a stereodifferentiation of the chemical environments induced by remote electron-withdrawing substituents which produces remarkable Z/E diastereosele