401838-40-2

Basic information

• Product Name: C₂₁H₂₁NO₂
• CAS NO: 401838-40-2
• Molecular Weight: 319.403
• Mol File: 401838-40-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₂₁H₂₁NO₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₁H₂₁NO₂(401838-40-2)
• EPA Substance Registry System: C₂₁H₂₁NO₂(401838-40-2)

Safety Data

• Hazardous Substances Data: 401838-40-2(Hazardous Substances Data)

Upstream product

• 493-72-1 5-phenyl-cyclohexane-1,3-dione 
• 2057-01-4 2-acetyl-5-phenylcyclohexane-1,3-dione 
• 95-53-4 o-toluidine 

Relevant articles and documents

Novel colchicine-site binders with a cyclohexanedione scaffold identified through a ligand-based virtual screening approach

Vascular disrupting agents (VDAs) constitute an innovative anticancer therapy that targets the tumor endothelium, leading to tumor necrosis. Our approach for the identification of new VDAs has relied on a ligand 3-D shape similarity virtual screening (VS) approach using the ROCS program as the VS tool and as query colchicine and TN-16, which both bind the α,β-tubulin dimer. One of the hits identified, using TN-16 as query, has been explored by the synthesis of its structural analogues, leading to 2-(1-((2-methoxyphenyl) amino)ethylidene)-5-phenylcyclohexane-1,3-dione (compound 16c) with an IC 50 = 0.09 ± 0.01 μM in HMEC-1 and BAEC, being 100-fold more potent than the initial hit. Compound 16c caused cell cycle arrest in the G2/M phase and interacted with the colchicine-binding site in tubulin, as confirmed by a competition assay with N,N′-ethylenebis(iodoacetamide) and by fluorescence spectroscopy. Moreover, 16c destroyed an established endothelial tubular network at 1 μM and inhibited the migration and invasion of human breast carcinoma cells at 0.4 μM. In conclusion, our approach has led to a new chemotype of promising antiproliferative compounds with antimitotic and potential VDA properties.