26482-53-1

Usage

Uses

Used in Pharmaceutical Industry:
1-C-Ethylaminoadamantane is used as an antiviral agent for the prevention and treatment of specific strains of influenza. It is effective in blocking the M2 protein, preventing the virus from replicating within the host cell.
1-C-Ethylaminoadamantane is also used as a neuromodulatory agent in the management of Parkinson's disease and other movement disorders. It helps alleviate symptoms by affecting the production of dopamine, a neurotransmitter responsible for motor control.
However, the effectiveness of 1-C-ethylaminoadamantane has been compromised due to increased resistance among some strains of influenza. Additionally, it may cause side effects such as insomnia, dizziness, constipation, and in some cases, hallucinations and psychosis.

InChI:InChI=1/C12H21N/c13-2-1-12-6-9-3-10(7-12)5-11(4-9)8-12/h9-11H,1-8,13H2/p+1

Upstream product

• 16269-13-9 1-Carboxymethyladamantane nitrile 
• 19835-38-2 1-adamantylacetyl chloride 
• 36949-72-1 1-<2-(mesyloxy)ethyl>adamantane 
• 6240-11-5 2-(adamant-1-yl)ethanol 
• 773-37-5 1-(2-bromo-ethyl)-adamantane 
• 4942-47-6 (adamant-1-yl)-acetic acid 
• 26831-49-2 2-(adamantane-1-yl)ethyl azide 
• 19026-73-4 2-(1-adamantyl)acetamide 

Downstream Products

• 40283-73-6 Thiosulfuric acid S-[N-(2-adamantan-1-yl-ethyl)-carbamimidoylmethyl] ester 
• 1118763-27-1 3-(2-adamantan-1-ylethyl)-2-(2,6-difluorophenyl)thiazolidin-4-one 
• 1118763-22-6 3-(2-adamantan-1-ylethyl)-2-(2,6-dichlorophenyl)thiazolidin-4-one 
• 1118763-20-4 3-(2-adamantan-1-ylethyl)-2-(3,4,5-trimethoxyphenyl)thiazolidin-4-one 
• 137795-78-9 (S)-4-(2-Adamantan-1-yl-ethylcarbamoyl)-4-benzyloxycarbonylamino-butyric acid benzyl ester 
• 312749-17-0 2-(adamantan-1-yl)-N-benzylethan-1-amine 

Relevant academic research and scientific papers

Multiple Halogenation of Aliphatic C?H Bonds within the Hofmann–L?ffler Manifold

An innovative approach to position-selective polyhalogenation of aliphatic hydrocarbon bonds is presented. The reaction proceeded within the Hofmann-L?ffler manifold with amidyl radicals as the sole mediators to induce selective 1,5- and 1,6-hydrogen-atom transfer followed by halogenation. Multiple halogenation events of up to four innate C?H bond functionalizations were accomplished. The broad applicability of this new entry into polyhalogenation and the resulting synthetic possibilities were demonstrated for a total of 27 different examples including mixed halogenations.

Synthesis and anti-HIV studies of 2- and 3-adamantyl-substituted thiazolidin-4-ones

A series of novel thiazolidin-4-ones bearing a lipophilic adamantyl substituent at position 2 or 3 were synthesized. A majority of them showed a modest anti-HIV-1 activity, whereas 2-adamantan-1-yl-3-(4,6-dimethylpyrimidin-2-yl)-thiazolidin-4-one (8) was endowed with a remarkable antiviral potency (EC50 = 0.67 μM). The new series of compounds (22-29) with an adamantyl moiety at the 3-position of the thiazolidinone ring showed good to modest anti-HIV-1 activity (EC50 = 1.0-11 μM) but also pronounced cytostatic activity. For example 24, 26 and 29 showed an EC50 of 1.0-2.0 μM, while the 50% effective concentrations for 23 and 28 were 7.8 and 11.0 μM, respectively. X-ray studies and quantum chemical calculations revealed that the anti-HIV activity of the compounds strongly depends on their dipole moments and conformation of the thiazolidinones.

Photoinduced hydrogen atom abstraction in N-(adamantyl)phthalimides: structure-reactivity study in the solid state

Adamantyl-functionalized phthalimides were synthesized and the probability of intramolecular photochemical hydrogen atom abstraction in the solid state analyzed by X-ray crystallographic analyses. These analyses and solid-state photolyses showed that the parameters determining photochemical reactivity for typical carbonyl compounds in the solid state can also be extended to phthalimides. Only N-(2-adamantyl)phthalimide underwent a solid-state photochemical reaction, which is the first example in the phthalimide series. This reaction is regio- and stereoselective, resulting in an endo-alcohol. On the other hand, the photoreaction of N-(2-adamantyl)phthalimide in solution gives an exo-alcohol as the main product together with an endo-alcohol and a benzazepindione.

Structure-activity relationships in the binding of chemically derivatized CD4 to gp120 from human immunodeficiency virus

The first step in HIV infection is the binding of the envelope glycoprotein gp120 to the host cell receptor CD4. An interfacial "Phe43 cavity" in gp120, adjacent to residue Phe43 of gp120-bound CD4, has been suggested as a potential target for therapeutic intervention. We designed a CD4 mutant (D1D2F43C) for site-specific coupling of compounds for screening against the cavity. Altogether, 81 cysteine-reactive compounds were designed, synthesized, and tested. Eight derivatives exceeded the affinity of native D1D2 for gp120. Structure-activity relationships (SAR) for derivatized CD4 binding to gp120 revealed significant plasticity of the Phe43 cavity and a narrow entrance. The primary contacts for compound recognition inside the cavity were found to be van der Waals interactions, whereas hydrophilic interactions were detected in the entrance. This first SAR on ligand binding to an interior cavity of gp120 may provide a starting point for structure-based assembly of small molecules targeting gp120-CD4 interaction.

Tnf-alpha production inhibitors

A purpose of the present invention is to provide TNF-α production inhibitors being useful as therapeutic agents for autoimmune diseases such as rheumatoid arthritis. Novel compounds having the structure represented by the general formula [1] or salts ther