1381884-63-4

Upstream product

• 5664-21-1 cyclohexylacetaldehyde 
• 67-64-1 acetone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 

Downstream Products

• 1381884-81-6 (4R,5S)-3-(4-chlorobenzoyl)-4-cyclohexylmethyl-5-(2,5,5-trimethyl-[1,3]-dioxan-2-yl)oxazolidin-2-one 
• 1381884-68-9 (4R,5S)-5-acetyl-4-cyclohexylmethyloxazolidin-2-one 
• 17844-66-5 [1,1'-bi(cyclohexane)]-3,5-dione 
• 1609374-89-1 4-acetyl-[1,1'-bi(cyclohexane)]-3,5-dione 
• 1609374-91-5 4-(1-((2-methoxyphenyl)amino)ethylidene)-[1,1'-bi(cyclohexane)]-3,5-dione 

Relevant academic research and scientific papers

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.

Formal asymmetric enone aminohydroxylation: Organocatalytic one-pot synthesis of 4,5-disubstituted oxazolidinones

A formal asymmetric organocatalytic aminohydroxylation reaction of enones has been achieved via an aziridination-double SN2 sequence. As a part of the reaction design, the generated amino alcohol products are isolated as the corresponding oxazolidinones in good yields and excellent stereoselectivities.