62058-13-3

Basic information

• Product Name: Cis-4-Aminoadamantan-1-ol
• Synonyms: Cis-4-Aminoadamantan-1-ol;CL226
• CAS NO: 62058-13-3
• Molecular Formula: C10H17NO
• Molecular Weight: 167.24808
• Mol File: 62058-13-3.mol
• Article Data: 26

Chemical Properties

• Melting Point: >250℃ (SUB.)
• Boiling Point: 276℃
• Flash Point: 120℃
• Appearance: /
• Density: 1.205
• CAS DataBase Reference: Cis-4-Aminoadamantan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: Cis-4-Aminoadamantan-1-ol(62058-13-3)
• EPA Substance Registry System: Cis-4-Aminoadamantan-1-ol(62058-13-3)

Safety Data

• Hazardous Substances Data: 62058-13-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cis-4-Aminoadamantan-1-ol is used as a building block in organic chemistry for the synthesis of pharmaceuticals, particularly for the development of drugs targeting neurological and psychiatric disorders. Its unique structure and properties make it a promising candidate for drug discovery and design.
Used in Medicinal Chemistry:
Cis-4-Aminoadamantan-1-ol is used as a key intermediate in the synthesis of various medicinal compounds. Its versatile chemical properties allow for the development of novel therapeutic agents with potential applications in treating a wide range of diseases and conditions.
Used in Antiviral Research:
Cis-4-Aminoadamantan-1-ol is being studied for its potential antiviral properties. Its unique structure and interactions with biological targets may offer new avenues for the development of antiviral drugs, particularly against challenging viral infections.
Used in Antimalarial Research:
Cis-4-Aminoadamantan-1-ol is also being investigated for its potential antimalarial properties. Its ability to target specific biological pathways involved in malaria parasite replication and survival may lead to the development of new antimalarial drugs, addressing the growing need for effective treatments against drug-resistant strains of the disease.

InChI:InChI=1S/C10H17NO/c11-9-7-1-6-2-8(9)5-10(12,3-6)4-7/h6-9,12H,1-5,11H2/t6?,7-,8?,9?,10-/m0/s1

Upstream product

• 13074-39-0 N-(2-adamantyl)amine 
• 353241-69-7 C₁₂H₁₈N₂O₄ 
• 20098-14-0 5-hydroxyadamantan-2-one 
• 700-58-3 adamantanone 
• 20098-14-0 chemantane 
• 1240255-60-0 trans-4-((S)-1-phenylethylamino)adamantan-1-ol 
• 20098-19-5 1-hydroxy-4-aminoadamantane hydrochloride 
• 20098-18-4 5-hydroxy-adamantan-2-one oxime 
• 10523-68-9 adamantan-2-amine hydrochloride 

Downstream Products

• 944118-01-8 4-{[(1R,2r,3S,5s,7s)-5-hydroxyadamantan-2-yl]amino}-1H-pyrrolo[2,3-b]pyridine-5-carboxamide 
• 944118-01-8 4-{[(1R,2s,3S,5s,7s)-5-hydroxy-2-adamantyl]amino}-1H-pyrrolo[2,3-b]pyridine-5-carboxamide 
• 62058-03-1 (1u202fs,3R,4s,5S,7s)-4-aminoadamantan-1-ol 

Relevant articles and documents

An expeditious preparation of E-2-amino-5-hydroxyadamantane and its Z-isomer

Reductive amination of 5-hydroxy-2-adamantanone with S-α-methylbenzylamine using 5% Rh-C as the catalyst in the presence of Al(iOPr)3 gave a 3:1 mixture of the E- and Z-5-hydroxy-adamantane-1-phenethylamines. Choice of catalyst, concentration,

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.

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.

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.

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

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.

2, 4 -DIAMINOPYRIMIDINE DERIVATIVES AS PROTEIN KINASE INHIBITORS

The present invention relates to novel pyrimide derivatives of formula (I): that are useful as kinase inhibitors. More particularly, the present invention relates to novel pyrimidine compounds, methods for their preparation, pharmaceutical compositions containing these compounds and uses of these compounds in the treatment of proliferative disorders.

Imidazopyridine derivatives as JAK inhibitors

New imidazopyridine derivatives having the chemical structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Janus Kinases (JAK).

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

COMPOUND HAVING 11 ?-HSD1 INHIBITORY ACTIVITY

The present invention provides compounds having excellent 11β-HSD1 inhibitory activity. A compound represented by the following formula (I): [wherein X1 represents an oxygen atom, or the formula -(CR11R12)p-, etc., Y1 represents a hydrogen atom, a hydroxyl group, etc., Z1 represents an oxygen atom or the formula -(NR14)-, R1 represents a hydrogen atom, a halogen atom, a cyano group, a C1-4 alkyl group, a C1-4 alkyl group substituted with 1 to 3 halogen atoms, a C1-4 alkoxy group, a C1-4 alkoxycarbonyl group, a carboxyl group, a carbamoyl group, or an amino group, and m represents an integer of 1 or 2, and R2 represents a hydrogen atom or a C1-4 alkyl group, and n represents an integer of 1 or 2].