5689-59-8

Basic information

• Product Name: N-ADAMANTAN-1-YL-2-CHLORO-ACETAMIDE
• Synonyms: AKOS USSH-4110476;1-CHLOROACETYLAMINOADAMANTANE;N-(1-ADAMANTYL)-2-CHLOROACETAMIDE;N-ADAMANTAN-1-YL-2-CHLORO-ACETAMIDE;N-(1-Adamantyl)chloroacetamide;N-(1-adamantyl)-2-chloro-ethanamide;N-Chloroacetyl-1-aminoadamantane;Acetamide, 2-chloro-N-tricyclo(3.3.1.1(3,7))dec-1-yl- (9CI)
• CAS NO: 5689-59-8
• Molecular Formula: C₁₂H₁₈ClNO
• Molecular Weight: 227.73
• Product Categories: Adamantane derivatives
• Mol File: 5689-59-8.mol
• Article Data: 28

Chemical Properties

• Melting Point: 120-121℃
• Boiling Point: 385.3°Cat760mmHg
• Flash Point: 186.8°C
• Appearance: /
• Density: 1.20±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 3.84E-06mmHg at 25°C
• Refractive Index: 1.547
• PKA: 13.94±0.20(Predicted)
• CAS DataBase Reference: N-ADAMANTAN-1-YL-2-CHLORO-ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ADAMANTAN-1-YL-2-CHLORO-ACETAMIDE(5689-59-8)
• EPA Substance Registry System: N-ADAMANTAN-1-YL-2-CHLORO-ACETAMIDE(5689-59-8)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 5689-59-8(Hazardous Substances Data)

Usage

General Description

N-ADAMANTAN-1-YL-2-CHLORO-ACETAMIDE is a chemical compound with the molecular formula C11H17ClNO. It is an amide derivative of 2-chloroacetic acid, with an adamantane substituent at the nitrogen atom. N-ADAMANTAN-1-YL-2-CHLORO-ACETAMIDE is used in organic synthesis and medicinal chemistry. It has potential applications in the development of pharmaceuticals and agrochemicals due to its unique molecular structure and properties. N-ADAMANTAN-1-YL-2-CHLORO-ACETAMIDE may be used as a building block in the synthesis of various biologically active compounds and can be modified to enhance its properties for specific applications.

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

• 665-66-7 amantadine hydrochloride 
• 79-04-9 chloroacetyl chloride 
• 768-95-6 1-adamanthanol 
• 79-07-2 Chloroacetamide 
• 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 

Downstream Products

• 768-94-5 1-Adamantanamine 
• 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 
• 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 articles and documents

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.

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.

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.