5854-75-1

Upstream product

• 768-95-6 1-adamanthanol 
• 3019-71-4 Trichloroacetyl isocyanate 
• 120542-14-5 C₁₉H₂₃NO₄ 
• 5854-52-4 1-adamantyl chloroformate 
• 917-61-3 sodium isocyanate 

Downstream Products

• 5854-72-8 1-Adamantylcarbazat 
• 17744-02-4 2-amino-adamantan-1-ol 

Relevant academic research and scientific papers

Synthesis of noradamantane derivatives by ring-contraction of the adamantane framework

We describe a triflic acid promoted cascade reaction of adamantane derivatives consisting of a decarboxylation of N-methyl protected cyclic carbamates and a subsequent intramolecular nucleophilic 1,2-alkyl shift to generate ring contracted iminium triflates. This reaction expands the family of similar transformations, such as Wagner-Meerwein-, Demjanov-Tiffeneau-, Meinwald- or (semi-)pinacol-rearrangement. It allows the preparation of noradamantane derivatives in a few steps, starting from simple hydroxy-substituted adamantane precursors.

Synthesis of 8-Aminoquinolines by Using Carbamate Reagents: Facile Installation and Deprotection of Practical Amidating Groups

Described herein is the development of practical routes to 8-aminoquinolines by using readily installable and easily deprotectable amidating reagents. Two scalable procedures were optimized under RhIII-catalyzed conditions: i) the use of pre-generated chlorocarbamates and ii) a two-step one-pot process that directly employs carbamates. Both approaches are highly convenient for the gram-scale synthesis of 8-aminoquinolines under mild conditions. Facile deprotection of the synthetically versatile amidating groups was achieved under the Pd-catalyzed transfer hydrogenation conditions with simultaneous deoxygenation of quinoline N-oxides, thus yielding 8-aminoquinolines in excellent overall efficiency.

Structure-activity relationships of a small-molecule inhibitor of the PDZ domain of PICK1

Recently, we described the first small-molecule inhibitor, (E)-ethyl 2-cyano-3-(3,4-dichlorophenyl)acryloylcarbamate (1), of the PDZ domain of protein interacting with Cα-kinase 1 (PICK1), a potential drug target against brain ischemia, pain and cocaine addiction. Herein, we explore structure-activity relationships of 1 by introducing subtle modifications of the acryloylcarbamate scaffold and variations of the substituents on this scaffold. The configuration around the double bond of 1 and analogues was settled by a combination of X-ray crystallography, NMR and density functional theory calculations. Thereby, docking studies were used to correlate biological affinities with structural considerations for ligand-protein interactions. The most potent analogue obtained in this study showed an improvement in affinity compared to 1 and is currently a lead in further studies of PICK1 inhibition.

PYRIDAZINONE DERIVATIVES AND USE THEREOF AS P2X7 RECEPTOR INHIBITORS

Novel pyridazinone compounds of formula (I), which inhibit the purinergic P2X7 receptor and are useful for prevention, therapy and improvement of inflammatory and immunological diseases.

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.

Convenient Preparation of Alkyl Benzyl Imidodicarbonates, Useful Reagents for the Direct Synthesis of Protected Amines

New mixed alkyl benzyl imidodicarbonates were prepared by reaction of benzyloxycarbonyl isocyanate with appropriate alcohols.This simple procedure also furnished alternative, more convenient routes to dibenzyl and benzyl 9-fluorenylmethyl imidodicarbonates.The substances are of interest as potential Gabriel reagents.Completely selective removal of one of the alkoxycarbonyl groups from the N-atom of the imidodicarbonates was demonstrated in several instances, giving benzyl carbamate or the alternative carbamate.