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

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

Uses

Used in Pharmaceutical Research:
2-(4-(adamantan-1-yl)phenoxy)acetic acid is utilized as a research compound for exploring its pharmacological properties and therapeutic effects. Its structural properties and functional groups make it a valuable tool for studying potential interactions with biological systems, which could lead to the development of new drugs and therapies.
Used in Drug Development:
In the pharmaceutical industry, 2-(4-(adamantan-1-yl)phenoxy)acetic acid is used as a starting material or intermediate in the synthesis of new drugs. Its unique structure and functional groups offer opportunities for chemical modifications and optimization, potentially leading to the discovery of novel therapeutic agents with improved efficacy and safety profiles.
Further research is necessary to fully understand the potential applications and mechanisms of action of 2-(4-(adamantan-1-yl)phenoxy)acetic acid, as well as to evaluate its safety and efficacy in various therapeutic areas.

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

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

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 
• 1435933-39-3 C₂₆H₃₃N₃O₃ 
• 934593-92-7 AC₁-001 
• 313548-34-4 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-benzoic acid 
• 959857-83-1 5-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-nicotinic acid methyl ester 

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.

Methyl 3-(3-(4-(2,4,4-Trimethylpentan-2-yl)phenoxy)-propanamido)benzoate as a Novel and Dual Malate Dehydrogenase (MDH) 1/2 Inhibitor Targeting Cancer Metabolism

Previously, we reported a hypoxia-inducible factor (HIF)-1 inhibitor LW6 containing an (aryloxyacetylamino)benzoic acid moiety inhibits malate dehydrogenase 2 (MDH2) using a chemical biology approach. Structure-activity relationship studies on a series of (aryloxyacetylamino)benzoic acids identified selective MDH1, MDH2, and dual inhibitors, which were used to study the relationship between MDH enzyme activity and HIF-1 inhibition. We hypothesized that dual inhibition of MDH1 and MDH2 might be a powerful approach to target cancer metabolism and selected methyl-3-(3-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanamido)-benzoate (16c) as the most potent dual inhibitor. Kinetic studies revealed that compound 16c competitively inhibited MDH1 and MDH2. Compound 16c inhibited mitochondrial respiration and hypoxia-induced HIF-1α accumulation. In xenograft assays using HCT116 cells, compound 16c demonstrated significant in vivo antitumor efficacy. This finding provides concrete evidence that inhibition of both MDH1 and MDH2 may provide a valuable platform for developing novel therapeutics that target cancer metabolism and tumor growth.

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.

Synthesis and biological evaluation of ortho-carborane containing benzoxazole as an inhibitor of hypoxia inducible factor (HIF)-1 transcriptional activity

ortho-Carborane and adamantane containing benzoxazoles were synthesized by intramolecular dehydration of the corresponding phenoxyacetanilides. Among the compounds synthesized, ortho-carborane containing benzoxazole 2b which has a carboxylic group on the benzoxazole ring, exhibited significant inhibition of hypoxia-induced HIF-1 transcriptional activity with the IC50 value of 14.4 μM toward HeLa cell-based reporter gene assay.

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.

Boron-containing phenoxyacetanilide derivatives as hypoxia-inducible factor (HIF)-1α inhibitors

A series of boron-containing phenoxyacetanilide derivatives 8a-f, 9a-f, 15, and 16 were synthesized as hypoxia-inducible factor (HIF)-1α inhibitors. Among the compounds synthesized, carboranylphenoxyacetanilide 16 (GN26361) was found to be a potent inhibitor against HIF-1α accumulation under hypoxic conditions and inhibited the hypoxia-induced HIF-1 transcriptional activity in HeLa cells (IC50 = 0.74 μM). Compound 16 suppressed hypoxia-induced HIF-1α accumulation and vascular endothelial growth factor mRNA expression in a concentration-dependent manner without affecting the expression of HIF-1α mRNA.

(Aryloxyacetylamino)benzoic acid analogues: A new class of hypoxia-inducible factor-1 inhibitors

Structural modification of a compound discovered during screening using an HRE-dependent reporter assay has revealed a novel class of HIF-1 inhibitors, which potently inhibit the HIF-1α protein accumulation and its target gene expression under hypoxic conditions in human hepatocellular carcinoma Hep3B cells.

Synthesis of (aryloxyacetylamino)-isonicotinic/nicotinic acid analogues as potent hypoxia-inducible factor (HIF)-1α inhibitors

We report a new series of HIF-1α inhibitors which were obtained through structural modifications of previously reported lead 1. The in vitro inhibitory potencies of newly synthesized compounds were evaluated against hypoxia-induced HIF-1 activation using

TRIFLUOROACETIC ANHYDRIDE AS A MEDIUM FOR ORGANIC REACTIONS. FUNCTIONAL SUBSTITUTION OF ADAMANTANE AND ITS DERIVATIVES

The role of trifluoroacetic anhydride during the oxidation of adamantane and its derivatives with sulfuric acid was studied. 1-Adamantanol, 1-(4-methyl-3-nitrophenyl)-3-adamantanol.The latter was used without isolation from the reaction mixture for the production of 1-adamantanecarboxylic acid, N-(1-adamantyl)acetamide, 1-(1-adamantyl)butan-1-ol, 1-(4-methylphenyl)adamantane, 4-(1-adamantyl)phenoxyacetic acid, 4-(1-adamantyl)acetanilide, and 4-(1-adamantyl)bromobenzene.