5689-59-8

Usage

Uses

Used in Organic Synthesis:
N-ADAMANTAN-1-YL-2-CHLORO-ACETAMIDE is used as a building block in organic synthesis for the creation of various biologically active compounds. Its adamantane substituent and chloroacetamide group provide a versatile platform for further chemical modifications and reactions.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, N-ADAMANTAN-1-YL-2-CHLORO-ACETAMIDE is utilized for the development of pharmaceuticals and agrochemicals. Its unique molecular structure allows for the design of novel compounds with potential therapeutic and pesticidal properties.
Used in Pharmaceutical Development:
N-ADAMANTAN-1-YL-2-CHLORO-ACETAMIDE is used as a key intermediate in the synthesis of pharmaceuticals. Its adamantane core and functional groups can be modified to enhance the compound's properties, such as solubility, stability, and bioavailability, for specific therapeutic applications.
Used in Agrochemical Development:
In agrochemical research, N-ADAMANTAN-1-YL-2-CHLORO-ACETAMIDE serves as a starting material for the development of new pesticides and herbicides. Its unique structure and reactivity can be exploited to create compounds with improved efficacy and selectivity against target pests or weeds.
Overall, N-ADAMANTAN-1-YL-2-CHLORO-ACETAMIDE's diverse applications in organic synthesis, medicinal chemistry, pharmaceutical development, and agrochemical research highlight its potential as a valuable chemical compound with a wide range of uses.

InChI:InChI=1/C12H18ClNO/c13-7-11(15)14-12-4-8-1-9(5-12)3-10(2-8)6-12/h8-10H,1-7H2,(H,14,15)

Upstream product

• 768-95-6 1-adamanthanol 
• 107-14-2 chloroacetonitrile 
• 593-71-5 Chloroiodomethane 
• 4411-25-0 1-adamantyl isocyanate 
• 22118-09-8 2-bromoacetyl chloride 
• 768-94-5 1-Adamantanamine 
• 79-07-2 Chloroacetamide 
• 79-04-9 chloroacetyl chloride 
• 665-66-7 amantadine hydrochloride 

Downstream Products

• 53783-83-8 N-(adamantan-1-yl)-2-(2-(dimethylamino)ethoxy)acetamide 
• 1349186-21-5 N-((1s,3s)-adamantan-1-yl)-2-(4,5-diphenyl-1H-imidazol-1-yl)acetamide 
• 37818-93-2 N-(adamantan-1-yl)ethane-1,2-diamine 
• 768-94-5 1-Adamantanamine 
• 117651-72-6 N-Adamantan-1-yl-2-(3-ethyl-2-imino-2,3-dihydro-benzoimidazol-1-yl)-acetamide; hydrochloride 
• 117651-71-5 N-Adamantan-1-yl-2-(2-imino-3-methyl-2,3-dihydro-benzoimidazol-1-yl)-acetamide; hydrochloride 
• 117651-73-7 N-Adamantan-1-yl-2-(3-butyl-2-imino-2,3-dihydro-benzoimidazol-1-yl)-acetamide; hydrochloride 

Relevant academic research and scientific papers

Conjugation of aminoadamantanes by copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition

Four variants of conjugation of aminoadamantanes with 1,2,3-triazole- and ditriazolecontaining spacers by copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition of azido- and propargyl-containing aminoadamantanes were suggested.

De novo Design of SARS-CoV-2 Main Protease Inhibitors

The COVID-19 pandemic prompted many scientists to investigate remedies against SARS-CoV-2 and related viruses that are likely to appear in the future. As the main protease of the virus, M Pro, is highly conserved among coronaviruses, it has emerged as a prime target for developing inhibitors. Using a combination of virtual screening and molecular modeling, we identified small molecules that were easily accessible and could be quickly diversified. Biochemical assays confirmed a class of pyridones as low micromolar noncovalent inhibitors of the viral main protease.

Novel selective ido1 inhibitors with isoxazolo[5,4-d]pyrimidin-4(5h)-one scaffold

Indoleamine 2,3-dioxygenase 1 (IDO1) is a promising target in immunomodulation of several pathological conditions, especially cancers. Here we present the synthesis of a series of IDO1 inhibitors with the novel isoxazolo[5,4-d]pyrimidin-4(5H)-one scaffold. A focused library was prepared using a 6-or 7-step synthetic procedure to allow a systematic investigation of the structure-activity relationships of the described scaffold. Chemistry-driven modifications lead us to the discovery of our best-in-class inhibitors possessing p-trifluoromethyl (23), p-cyclohexyl (32), or p-methoxycarbonyl (20, 39) substituted aniline moieties with IC50 values in the low micromolar range. In addition to hIDO1, compounds were tested for their inhibition of indoleamine 2,3-dioxygenase 2 and tryptophan dioxygenase, and found to be selective for hIDO1. Our results thus demon-strate a successful study on IDO1-selective isoxazolo[5,4-d]pyrimidin-4(5H)-one inhibitors, defining promising chemical probes with a novel scaffold for further development of potent small-molecule immunomodulators.

Application of acetyl amantadine piperazine (piperidine) compound as cerebral neuroprotective agent

The present invention discloses an application of acetamantadine piperazine (piperidine) compound as cerebral neuroprotective agent. The structure of the acetamantadine piperazine (piperidine) compound is novel, and the application of the acetamantadine p

Discovery of a Small-Molecule Inhibitor of Interleukin 15: Pharmacophore-Based Virtual Screening and Hit Optimization

Interleukin (IL)-15 is a pleiotropic cytokine, which is structurally close to IL-2 and shares with it the IL-2 β and γ receptor (R) subunits. By promoting the activation and proliferation of NK, NK-T, and CD8+ T cells, IL-15 plays important roles in innate and adaptative immunity. Moreover, the association of high levels of IL-15 expression with inflammatory and autoimmune diseases has led to the development of various antagonistic approaches targeting IL-15. This study is an original approach aimed at discovering small-molecule inhibitors impeding IL-15/IL-15R interaction. A pharmacophore and docking-based virtual screening of compound libraries led to the selection of 240 high-scoring compounds, 36 of which were found to bind IL-15, to inhibit the binding of IL-15 to the IL-2Rβ chain or the proliferation of IL-15-dependent cells or both. One of them was selected as a hit and optimized by a structure-activity relationship approach, leading to the first small-molecule IL-15 inhibitor with sub-micromolar activity.

Indium-Triflate-Catalyzed Ritter Reaction in Liquid Sulfur Dioxide

The use of liquid sulfur dioxide as a reaction solvent facilitates the Ritter reaction between alcohols and nitriles. In(OTf)3 was found to be a viable catalyst for this transformation. The newly developed catalytic conditions for the Ritter reaction were successfully applied to the synthesis of various amides, which were formed in good to excellent yields. The catalytic activation of secondary alcohols for Ritter reactions in liquid sulfur dioxide was also found to be effective.

Adamantanedicarboxylic deriv.

PROBLEM TO BE SOLVED: To provide an adamantane derivative which can be used as a novel resist material, especially a photoresist material in which acids are controlled by incorporating a unit or a structure capable of controlling acids into a monomer or a polymer.SOLUTION: An adamantane derivative represented by the formula (1), where Rrepresents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group, X represents a group selected from -O-, -NH-, -N(C(=O)R)-, Rto Reach represents a hydrogen atom, an alkyl group or an alkyl group substituted with a hydroxyl group or an ester group, Rand Rmay connect each other to form a ring, n represents an integer of 1 to 3, and asterisk represents a bond position, is provided.

Homologation of isocyanates with lithium carbenoids: A straightforward access to α-halomethyl- and α,α-dihalomethylamides

Treatment of widely available isocyanates with monohalolithium and dihalolithium carbenoids provides a valuable protocol for the one-pot preparation of α-halo- and α,α-dihaloacetamide derivatives. While monohalolithium carbenoids can be prepared by a smoo

Addition of lithium carbenoids to isocyanates: A direct access to synthetically useful N-substituted 2-haloacetamides

The addition of lithium carbenoids to isocyanates provides a versatile access to N-substituted 2-haloacetamides: the reaction tolerates the presence of variously functionalized substituents on the nitrogen atom, including sterically demanding ones and reactive halogens. No erosion of the enantiopurity was observed in the case of optically active isocyanates. One of the substrates prepared has been employed in Charette's type chemoselective addition of a Grignard reagent to access an α-chloroketone.

Reusable and highly active supported copper(i)-NHC catalysts for Click chemistry

Immobilised [Cu(NHC)] catalysts are reported for the preparation of 1,2,3-triazoles. In addition to showing outstanding catalytic activity, the catalyst systems are easy to prepare and can be recycled many times.