19835-38-2

Basic information

• Product Name: 1-ADAMANTANEACETYL CHLORIDE
• Synonyms: 1-ADAMANTANEACETYL CHLORIDE;1-ADAMANTYLACETYL CHLORIDE;2-(1-ADAMANTYL)ETHANOYL CHLORIDE;ADAMANTAN-1-YL-ACETYL CHLORIDE;AKOS BC-0495;17. 1-adamantaneacetyl chloride;Tricyclo[3.3.1.13,7]decane-1-acetyl chloride;2-(1-adamantyl)acetyl chloride
• CAS NO: 19835-38-2
• Molecular Formula: C₁₂H₁₇ClO
• Molecular Weight: 212.72
• Product Categories: Adamantane derivatives
• Mol File: 19835-38-2.mol

Chemical Properties

• Boiling Point: 281.1 °C at 760 mmHg
• Flash Point: 126℃
• Appearance: /
• Density: 1.179
• Vapor Pressure: 0.00363mmHg at 25°C
• Refractive Index: 1.537
• CAS DataBase Reference: 1-ADAMANTANEACETYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ADAMANTANEACETYL CHLORIDE(19835-38-2)
• EPA Substance Registry System: 1-ADAMANTANEACETYL CHLORIDE(19835-38-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 19835-38-2(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
1-Adamantaneacetyl chloride is used as an inhibitor for human 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) due to its potent inhibitory effects. This enzyme plays a crucial role in the regulation of glucocorticoid hormones, which are involved in various physiological processes, including inflammation, immune response, and stress. Inhibition of 11β-HSD1 can help in the development of therapeutic strategies for conditions such as type 2 diabetes, obesity, and cardiovascular diseases, where dysregulation of glucocorticoid hormones is observed.
2. Used in Chemical Synthesis:
1-Adamantaneacetyl chloride can also be utilized as a synthetic building block or reagent in the synthesis of various organic compounds, particularly those with adamantane-based structures. Its unique cage-like structure and reactive acetyl chloride group make it a valuable component in the development of novel molecules with potential applications in pharmaceuticals, materials science, and other areas.

InChI:InChI=1/C12H17ClO/c13-11(14)7-12-4-8-1-9(5-12)3-10(2-8)6-12/h8-10H,1-7H2

Upstream product

• 4942-47-6 (adamant-1-yl)-acetic acid 

Downstream Products

• 55759-60-9 1-Adamantan-1-yl-3-(triphenyl-λ⁵-phosphanylidene)-propan-2-one 
• 76308-70-8 1-cyclohexyl-2-(1-adamantyl)-1-ethanone 
• 27174-71-6 methyl 2-(adamantan-1-yl)acetate 
• 39917-55-0 1-(1-adamantyl)-2-methyl-2-propanol 
• 19835-39-3 1-(1-adamantyl)propan-2-one 
• 15782-66-8 ethyl 4-(adamant-1-yl)-phenyl acetate 
• 95477-26-2 1-Adamantan-1-yl-butan-2-ol 
• 78679-66-0 1-Adamantan-1-yl-butan-2-one 
• 136009-61-5 1-(2-Adamantan-1-yl-acetyl)-3-benzyl-2-(4-hydroxy-phenyl)-2,3-dihydro-1H-quinazolin-4-one 
• 136009-60-4 1-(2-Adamantan-1-yl-acetyl)-3-benzyl-2-(2-hydroxy-phenyl)-2,3-dihydro-1H-quinazolin-4-one 
• 136009-62-6 1-(2-Adamantan-1-yl-acetyl)-3-benzyl-2-(4-methoxy-phenyl)-2,3-dihydro-1H-quinazolin-4-one 
• 136009-63-7 1-adamantylacetyl-2-(2',4'-dimethoxyphenyl)-3-benzyl-1,2,3,4-tetrahydroquinazoline-4-one 
• 136009-59-1 1-(1'-adamantylacetyl)-2-(2',4'-dimethoxyphenyl)-3-(4'-methoxyphenyl)-1,2,3,4-tetrahydroquinazoline-4-one 
• 83699-45-0 S-<2-(Adamantan-1-carboxamido)ethyl>isothiouronium bromide 

Relevant articles and documents

Enantioresolution and chameleonic mimicry of 2-Butanol with an adamantylacetyl derivative of cholic acid

[3β,5β,7α,12α]-3[(Adamantyl-l-acetyl)-amino] -7-12-dihydroxycholan-24-oic acid (AdCH2CA) was synthesized by the reaction between 1-adamantyl acetyl chloride and the methyl ester of 3β-amino-cholic acid and hydrolysis of the ester. The acid was recrystallized from racemic 2-butanol (0.1% water). Crystals are orthorhombic (P212121) and form inclusion complexes with water and 2-butanol with a 1:1:1 stoichiometry. Only the S-enantiomer is included into the structure of the crystal, exhibiting a chameleonic mimicry with the steroid bilayers. The isolation of crystals allows the enantioresolution of the racemate with a high purity (≈99%) of S-2-butanol. The steroid molecules are disposed in an antiparallel orientation in the hydrophobic layer and a parallel orientation in the hydrophilic one.

Carbonic anhydrase inhibitors: Aromatic and heterocyclic sulfonamides incorporating adamantyl moieties with strong anticonvulsant activity

A series of aromatic/heterocyclic sulfonamides incorporating adamantyl moieties were prepared by reaction of aromatic/heterocyclic aminosulfonamides with the acyl chlorides derived from adamantyl-1-carboxylic acid and 1-adamantyl-acetic acid. Related derivatives were obtained from the above-mentioned aminosulfonamides with adamantyl isocyanate and adamantyl isothiocyanate, respectively. Some of these derivatives showed good inhibitory potency against two human CA isozymes involved in important physiological processes, CA I, and CA II, of the same order of magnitude as the clinically used drugs acetazolamide and methazolamide. The lipophilicity of the best CA inhibitors was determined and expressed as their experimental logk ′ IAM and theoretical ClogP value. Their lipophilicity was propitious with the crossing of the blood-brain barrier (logk′ IAM>1.35). The anticonvulsant activity of some of the best CA inhibitors reported here has been evaluated in a MES test in mice. After intraperitoneal injection (30mgkg-1), compounds A8 and A9 exhibited a high protection against electrically induced convulsions (>90%). Their ED50 was 3.5 and 2.6mgkg-1, respectively.

Full characterization and some reactions of 1-(2-adamantyl)-3-(1-adamantyl) aziridin-2-one

(Chemical Equation Presented) We found that 1-(2-adamantyl)-3-tert- butylaziridin-2-one (5a) is unstable. It slowly decomposes at room temperature, although detectable by IR spectroscopy (1840 cm-1 band in CCl 4). On the other hand, a closely related analogue, 1-(2-adamantyl)-3-(1-adamantyl)aziridin-2-one (5b), is very stable, in concurrence with an earlier report [1]. We fully characterized aziridinone 5b, identified its thermal decomposition products (7 and 8) and reacted it with two aprotic ionic (tBuO- and HO-) and one protic non-ionic nucleophile (benzylamine). All three products (9b, 10, and 11) result from exclusive cleavage of the lactam (1-2) bond.

Synthesis and evaluation of bifunctional PTP4A3 phosphatase inhibitors activating the ER stress pathway

We developed JMS-053, a potent inhibitor of the dual specificity phosphatase PTP4A3 that is potentially suitable for cancer therapy. Due to the emerging role of the unfolded protein response (UPR) in cancer pathology, we sought to identify derivatives that combine PTP4A3 inhibition with induction of endoplasmatic reticulum (ER) stress, with the goal to generate more potent anticancer agents. We have now generated bifunctional analogs that link the JMS-053 pharmacophore to an adamantyl moiety and act in concert with the phosphatase inhibitor to induce ER stress and cell death. The most potent compound in this series, 7a, demonstrated a ca. 5-fold increase in cytotoxicity in a breast cancer cell line and strong activation of UPR and ER stress response genes in spite of a ca. 13-fold decrease in PTP4A3 inhibition. These results demonstrate that the combination of phosphatase inhibition with UPR/ER-stress upregulation potentiates efficacy.

Four-Directional synthesis of adamantane derivatives

1-Adamantanemethanol, 1,3-adamantanedimethanol and 1,3,5,7-adamantanetetramethanol were converted into adamantanes functionalized with one or four (2R,1S)-2-formyl-1-cyclopropyl residues using Charette enantioselective cyclopropanation reactions and with one, two or four 4-ethoxy- (or 4-t-butoxy)-3-diazo-2,4- dioxobutyl residues from aldehyde and diazo-acetate ester condensation reactions by 1-directional, 2- directional or 4-directional syntheses. The synthesis of adamantane fused to cyclopentadiene is also reported. 'Equation Presented'.

Highly Porous Hybrid Metal–Organic Nanoparticles Loaded with Gemcitabine Monophosphate: a Multimodal Approach to Improve Chemo- and Radiotherapy

Nanomedicine recently emerged as a novel strategy to improve the performance of radiotherapy. Herein we report the first application of radioenhancers made of nanoscale metal-organic frameworks (nanoMOFs), loaded with gemcitabine monophosphate (Gem-MP), a radiosensitizing anticancer drug. Iron trimesate nanoMOFs possess a regular porous structure with oxocentered Fe trimers separated by around 5 ? (trimesate linkers). This porosity is favorable to diffuse the electrons emitted from nanoMOFs due to activation by γ radiation, leading to water radiolysis and generation of hydroxyl radicals which create nanoscale damages in cancer cells. Moreover, nanoMOFs act as “Trojan horses”, carrying their Gem-MP cargo inside cancer cells to interfere with DNA repair. By displaying different mechanisms of action, both nanoMOFs and incorporated Gem-MP contribute to improve radiation efficacy. The radiation enhancement factor of Gem-MP loaded nanoMOFs reaches 1.8, one of the highest values ever reported. These results pave the way toward the design of engineered nanoparticles in which each component plays a role in cancer treatment by radiotherapy.

Prodrug compound and application thereof in treatment of cancer

The present invention provides a compound indicated by a formula (I), pharmaceutically acceptable salts or esters thereof, a pharmaceutical composition of the compound, and the use of the compound andthe pharmaceutical composition in inhibition or regulation of tyrosine kinase activity, and treatment of tyrosine kinase mediated disease symptoms or disorders including cancer.

3D-printed cartridge system for in-flow photo-oxygenation of 7-aminothienopyridinones

A 3D-printed polypropylene (PP) continuous-photoflow cell based on a modular cartridge system was developed for the photo-oxygenation of 7-aminothieno[3,2-c]pyridin-4(5H)-ones, using ambient air as the sole co-reactant. This strategy takes advantage of the versatility of 3D-printing to construct cost-effective meso-scale reactors. In addition to scalability, a short residence time (tR 2 min) in 100-W blue LED light that minimizes the formation of dark, insoluble decomposition products is a tangible benefit of this technology.

Strongly Entangled Triplet Acyl-Alkyl Radical Pairs in Crystals of Photostable Diphenylmethyl Adamantyl Ketones

Radical pairs generated in crystalline solids by bond cleavage reactions of triplet ketones offer the unique opportunity to explore a frontier of spin dynamics where rigid radicals are highly entangled as the result of short inter-radical distances, large

Ruthenium(II)-Catalyzed Enantioselective ?-Lactams Formation by Intramolecular C-H Amidation of 1,4,2-Dioxazol-5-Ones

We report the Ru-Catalyzed enantioselective annulation of 1,4,2-Dioxazol-5-Ones to furnish ?-Lactams in up to 97% yield and 98% ee via intramolecular carbonylnitrene C-H insertion. By employing chiral diphenylethylene diamine (dpen) as ligands bearing electron-Withdrawing arylsulfonyl substituents, the reactions occur with remarkable chemo- A nd enantioselectivities; the competing Curtius-Type rearrangement was largely suppressed. Enantioselective nitrene insertion to allylic/propargylic C-H bonds was also achieved with remarkable tolerance to the Ca?C and Ca‰iC bonds.