26496-36-6

Usage

InChI:InChI=1/C11H19N3O/c12-14-10(15)13-11-4-7-1-8(5-11)3-9(2-7)6-11/h7-9H,1-6,12H2,(H2,13,14,15)

Upstream product

• 4411-25-0 1-adamantyl isocyanate 
• 768-94-5 1-Adamantanamine 
• 65839-12-5 N-(adamantan-1-yl) S-ethyl carbamothioate 
• 25192-03-4 1-(ethoxycarbonylamino)adamantane 

Relevant academic research and scientific papers

Novel chelators based on adamantane-derived semicarbazones and hydrazones that target multiple hallmarks of Alzheimer's disease

Alzheimer's disease (AD) is characterized by multiple pathological hallmarks, including β-amyloid aggregation, oxidative stress, and metal dys-homeostasis. In the absence of treatments addressing its multi-factorial pathology, we designed novel multi-functional adamantane-based semicarbazones and hydrazones (1-12) targeting AD hallmarks. Of these, 2-pyridinecarboxaldehyde (N-adamantan-1-yl)benzoyl-4-amidohydrazone (10) was identified as the lead compound, which demonstrated: (1) pronounced iron chelation efficacy; (2) attenuation of CuII-mediated β-amyloid aggregation; (3) low cytotoxicity; (4) inhibition of oxidative stress; and (5) favorable characteristics for effective blood-brain barrier permeation. Structure-activity relationships revealed that pyridine-derived hydrazones represent a promising pharmacophore for future design strategies due to their ability to bind critical FeII pools. Collectively, the unique multi-functional activity of these agents provides a novel therapeutic strategy for AD treatment.

N-Substituted S-Alkyl Carbamothioates in the Synthesis of Nitrogen-containing Functional Derivatives of the Adamantane Series

Abstract: A series of new asymmetric ureas, urethanes, and other derivatives of the framework structure have been synthesized by the reactions of adamantan-1-yl isocyanate generated in situ by the thermolysis of carbamothioates with nitrogen-containing nucleophiles and alcohols.

Highly Regioselective Carbamoylation of Electron-Deficient Nitrogen Heteroarenes with Hydrazinecarboxamides

The use of hydrazinecarboxamides as a new class of carbamoylating agents has been established through the dehydrazinative Minisci reaction of electron-deficient nitrogen heteroarenes. A wide range of electron-deficient nitrogen heteroarenes, including isoquinoline, quinoline, pyridine, phenanthridine, quinoxaline, and phthalazine, underwent copper/acid-catalyzed oxidative carbamoylation with hydrazinecarboxamide hydrochlorides to afford structurally diverse nitrogen-heteroaryl carboxamides as single regioisomers in moderate to excellent yields. The functional group tolerance was substantially demonstrated in the direct carbamoylation of quinine obviating multistep sequences involving protecting groups and prefunctionalization of the heterocycle.

ADAMANTANE COMPOUNDS

The present invention relates to new multi-functional compounds that are useful in the treatment of neurodegenerative diseases, such as Alzheimer's disease, to the preparation of the compounds, and to compositions including the compounds. The present invention also relates to the use of the compounds, as well as compositions including the compounds, in treating or preventing neurodegenerative diseases.

Adamantane derivatives, part III*: Synthesis of some aminoadamantanes as novel antitumor aqents

New series of 1-(1-adamantyl)semicarbazide 3a, 1-(1-adamantyl)-4-(4-substituted phenyl)semicarbazides 3b-e, 1-(1-adamantyl)-3-(substituted aminosulfonyl)ureas 5a-g, 1-(1-adamantyl)-4-(1-adamantylamino-methylene)-semicarbazide 7, 1-(1-adamantyl)-4-(1-adama