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
• Article Data: 3

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

Novel antitumor agent that induces apoptosis in tumor cells through inhibition of the tyrosine kinase BCR/ABL.

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.

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.