241127-58-2

Basic information

• Product Name: 1-adamantyl 4-[(2,5-dihydroxyphenyl)methylamino]benzoate
• Synonyms: 1-adamantyl 4-[(2,5-dihydroxyphenyl)methylamino]benzoate;4-[[(2,5-Dihydroxyphenyl)methyl]amino]benzoicacidtricyclo[3.3.1.13,7]dec-1-ylester;Adaphostin
• CAS NO: 241127-58-2
• Molecular Formula: C₂₄H₂₇NO₄
• Molecular Weight: 393.48
• Product Categories: Amines;Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 241127-58-2.mol

Chemical Properties

• Boiling Point: 606.2°Cat760mmHg
• Flash Point: 320.4°C
• Appearance: white to beige/
• Density: 1.33g/cm³
• Vapor Pressure: 2.73E-15mmHg at 25°C
• Refractive Index: 1.661
• Storage Temp.: Desiccate at +4°C
• Solubility: DMSO: soluble20mg/mL, clear
• CAS DataBase Reference: 1-adamantyl 4-[(2,5-dihydroxyphenyl)methylamino]benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-adamantyl 4-[(2,5-dihydroxyphenyl)methylamino]benzoate(241127-58-2)
• EPA Substance Registry System: 1-adamantyl 4-[(2,5-dihydroxyphenyl)methylamino]benzoate(241127-58-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 241127-58-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Adamantyl 4-[(2,5-dihydroxyphenyl)methylamino]benzoate is used as a novel antitumor agent for its ability to induce apoptosis in tumor cells. The compound specifically targets and inhibits the tyrosine kinase BCR/ABL, which is a key enzyme involved in the development and progression of certain types of cancer. By inhibiting this enzyme, the compound can effectively suppress tumor growth and promote cell death in cancerous cells, making it a promising candidate for the development of new cancer therapies.
Used in Drug Delivery Systems:
In addition to its direct antitumor effects, 1-adamantyl 4-[(2,5-dihydroxyphenyl)methylamino]benzoate may also be utilized in the development of advanced drug delivery systems. Its unique molecular structure and properties could potentially be exploited to improve the delivery, bioavailability, and therapeutic outcomes of various drugs, particularly in the treatment of cancer. For instance, the compound could be incorporated into nanoparticles or other carrier systems to enhance the targeted delivery of chemotherapeutic agents, thereby increasing their efficacy and reducing side effects.

Biological Activity

p210 bcr/abl tyrosine kinase inhibitor (IC 50 = 14 μ M). Induces apoptosis in T-lymphoblastic human leukemia cell lines (IC 50 values range from 16.8 to 216.3 nM) in vitro . Displays selectivity for chronic myelogenous leukemia (CML) myeloid progenitors in vitro .

InChI:InChI=1/C24H27NO4/c26-21-5-6-22(27)19(10-21)14-25-20-3-1-18(2-4-20)23(28)29-24-11-15-7-16(12-24)9-17(8-15)13-24/h1-6,10,15-17,25-27H,7-9,11-14H2

Upstream product

• 62-23-7 4-nitro-benzoic acid 
• 122-04-3 4-nitro-benzoyl chloride 
• 768-95-6 1-adamanthanol 
• 968-84-3 1-adamantanol p-nitrobenzoate 
• 1194-98-5 2,5-Dihydroxybenzaldehyde 
• 241127-66-2 1-adamantyl 4-aminobenzoate 

Relevant articles and documents

Synthesis and biological evaluation of platensic alcohol as an adamantane surrogate in antitumor drug lead adaphostin

Adamantane has been widely used as a “lipophilic bullet” in drug discovery and development, due to its unique diamond-like architecture with benign pharmacological/ pharmaceutical properties. Platensimycin is a natural product isolated from a soil streptomycete, which contains an adamantane-like moiety extensively modified from a diterpenoid precursor. In the current study, platensic alcohol was semisynthesized from platensimycin and used as an adamantane surrogate in anticancer drug lead adaphostin. The resulting hybrid platensic alcohol/adaphostin compounds, eg. 4a and 4b, exhibited similar cytotoxic activity with adaphostin against the tested cancer cell lines. In particular, 4b generates significantly more reactive oxygen species (ROS) and shows stronger synergy with the clinically used histone deacetylase inhibitor vorinostat than adaphostin, probably due to the presence of two hydroquinone groups. Density functional theory calculation supports that there could be certain π-π stacking interaction in 4b in aqueous solution, which might explain that 4b has similar serum stability with adaphostin. Our study not only leads to the identification of 4b as a potent ROS generating agent, but showcases a simple scaffold hopping strategy to harvest lipophilic scaffolds from natural products.

Synthesis, structure-activity relationship, and p210bcr-abl protein tyrosine kinase activity of novel AG 957 analogs

A series of novel, sterically hindered lipophilic analogs of AG 957 was designed and synthesized as potential protein tyrosine kinase (PTK) inhibitors. The in vitro activity, in vivo anti-leukemia activity, and pharmacology of these PTK inhibitors were studied. Some aspects of the structure-activity relationship associated with the carboxylic acid, phenol ring, and linker modifications are discussed. We have demonstrated that the 1,4-hydroquinone moiety is essential for activity and that sterically hindered esters contribute to enhanced in vivo efficacy. Adaphostin (NSC 680410) has emerged as the improved compound with the maximum in vivo anti-leukemia hollow fiber activity, concordant with the original lead compound AG 957. Currently, adaphostin is undergoing preclinical toxicology studies.

Disubstituted lavendustin a analogs and pharmaceutical compositions comprising the analogs

Disubstituted lavendustin A analogs that are PTK inhibitors having antiproliferative activity are described. Preferred compounds of the present invention, without limitation, satisfy either Formula 1 or Formula 2. Currently preferred compounds ,based on in vivo biological activity, are 4'-adamantylbenzoate-1'-N-1,4-dihydroxybenzylamine and 4'-adamantylmethylbenzoate-1'-N-1,4-dihydroxybenzylamine. The present invention also provides pharmaceutical compositions comprising effective amounts of disubstituted lavendustin A analogs. Such compositions also may comprise other active ingredients, other materials conventionally used in the formulation of pharmaceutical composition, and mixtures thereof. The compounds and compositions of the present invention can be used for treating subjects to, for example, inhibit the proliferation of living cells in the treatment of proliferative diseases.