52804-26-9

Basic information

• Product Name: 2-(4-(adaMantan-1-yl)phenoxy)acetic acid
• Synonyms: 2-(4-(adaMantan-1-yl)phenoxy)acetic acid;(4-AdaMantan-1-yl-phenoxy)-aceticacid;(4-Tricyclo[3.3.1.1(3,7)]dec-1-ylphenoxy)acetic acid;[4-(Adamantyl-1)phenoxy]acetic acid;2-[4-(1-adamantyl)phenoxy]acetic acid;2-[4-(1-adamantyl)phenoxy]ethanoic acid;BAS 00285042;CBDivE_002637
• CAS NO: 52804-26-9
• Molecular Formula: C₁₈H₂₂O₃
• Molecular Weight: 286.36548
• Mol File: 52804-26-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 168-170℃ (acetic acid water )
• Boiling Point: 441.1°C at 760 mmHg
• Flash Point: 159.7°C
• Appearance: /
• Density: 1.226g/cm³
• Vapor Pressure: 1.47E-08mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-(4-(adaMantan-1-yl)phenoxy)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-(adaMantan-1-yl)phenoxy)acetic acid(52804-26-9)
• EPA Substance Registry System: 2-(4-(adaMantan-1-yl)phenoxy)acetic acid(52804-26-9)

Safety Data

• Hazardous Substances Data: 52804-26-9(Hazardous Substances Data)

Usage

General Description

2-(4-(adamantan-1-yl)phenoxy)acetic acid is a chemical compound with a molecular formula C20H27NO3. It is a derivative of adamantan-1-yl and phenoxyacetic acid, and is commonly used in medicinal and pharmaceutical research. The compound has a structure that consists of an adamantan-1-yl group attached to a phenoxyacetic acid group, making it a potential candidate for drug development and research. Its structural properties and functional groups allow for potential interactions with biological systems, making it of interest for studying pharmacological and therapeutic effects. Further research is needed to fully understand its potential applications and mechanisms of action.

InChI:InChI=1/C18H22O3/c19-17(20)11-21-16-3-1-15(2-4-16)18-8-12-5-13(9-18)7-14(6-12)10-18/h1-4,12-14H,5-11H2,(H,19,20)

Upstream product

• 281-23-2 adamantane 
• 122-59-8 2-phenoxyacetic acid 
• 108-95-2 phenol 
• 768-90-1 1-Adamantyl bromide 
• 29799-07-3 4-adamantylphenol 
• 52804-25-8 (4-adamantyl-1-yl-phenoxy) acetic acid ethyl ester 
• 1435933-48-4 C₂₂H₃₀O₃ 

Downstream Products

• 313548-31-1 methyl 3-(2-(4-adamantan-1-ylphenoxy)acetamido)benzoate 
• 934594-02-2 2-[2-(4-adamantan-1-ylphenoxy)acetylamino]benzoic acid methyl ester 
• 313548-32-2 4-[2-(4-adamantan-1-ylphenoxy)acetylamino]benzoic acid methyl ester 
• 934593-90-5 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-4-hydroxy-benzoic acid methyl ester 
• 934593-91-6 3-[2-(4-adamantan-1-ylphenoxy)acetylamino]-4-hydroxybenzoic acid 2-trimethylsilylethyl ester 
• 313548-34-4 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-benzoic acid 
• 934593-92-7 AC₁-001 
• 1435933-39-3 C₂₆H₃₃N₃O₃ 

Relevant articles and documents

Synthesis, biological evaluation and molecular docking studies of indeno [1, 2-c] pyrazol derivatives as inhibitors of mitochondrial malate dehydrogenase 2 (MDH2)

Hypoxia inducible factor-1 (HIF-1) is a pivotal transcription factor, which is strongly correlated with the induction of angiogenesis, tumor survival, metastasis, and cell proliferation, making it a pivotal therapeutic target for solid tumor therapeutic agents. Herein, a new series of multi-functional chemical probes were designed including principal groups, viz. adamantyl and indene, at various locations of the parent compound LW6. Molecular docking studies were performed on the designed compounds and their relationship with HIF-1α and malate dehydrogenase 2 (MDH2). Inhibition of MDH2 by our compounds was expected to decrease the NADH level. Indeed, treatment of the breast cancer cell line 4T1 led to a strong reduction of the NADH concentration. The greatest reduction in NADH production in mitochondria was observed with (E)-3-(4-((3r, 5r, 7r)-adamantan-1-yl) phenoxy)-N-(5-(piperidine-1-carbonyl)-1, 4-dihydroindeno [1, 2-c] pyrazol-3-yl) acrylamide (18: IC50 = 59 nM), and has the best inhibitory potential under hypoxic conditions (MCF-7: IC50 = 57 nM). This compound also gave one of the highest docking “higher than the score obtained with LW6 in parallel (?31.63 kcal/mol) in the initial docking runs (PDB Code: 4WLO). Other related compounds with good yields were also synthesized from docking results, and all the synthesized compounds (14, 18, 22, 26, 29, 30) were evaluated in vitro on human adenocarcinoma cell lines.

Discovery of potent transient receptor potential vanilloid 1 antagonists: Design and synthesis of phenoxyacetamide derivatives

We aimed to discover a novel type of transient receptor potential vanilloid 1 (TRPV1) antagonist because such antagonists are possible drug candidates for treating various disorders. We modified the structure of hit compound 7 (human TRPV1 IC50 = 411 nM) and converted its pyrrolidino group to a (hydroxyethyl)methylamino group, which substantially improved inhibitory activity (15d; human TRPV1 IC50 = 33 nM). In addition, 15d ameliorated bladder overactivity in rats in vivo.

Discovery of a novel series of benzimidazole derivatives as diacylglycerol acyltransferase inhibitors

A novel series of benzimidazole derivatives was prepared and evaluated for their diacylglycerol acyltransferase (DGAT) inhibitory activity using microsome from rat liver. Among the newly synthesized compounds, furfurylamine containing benzimidazole carboxamide 10j showed the most potent DGAT inhibitory effect (IC50= 4.4 μM) and inhibited triglyceride formation in HepG2 cells. Furthermore, compound 10j reduced body weight gain of Institute of Cancer Research mice on a high-fat diet and decreased levels of total triglyceride, total cholesterol, and LDL-cholesterol in the blood accompanied with a significant increase in HDL-cholesterol level.