1083067-13-3

Upstream product

• 55579-72-1 5-(4-fluoro-phenyl)-cyclohexane-1,3-dione 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 

Downstream Products

• 1083067-14-4 C₁₈H₂₀FNO₂ 
• 1609375-02-1 5-(4-fluorophenyl)-2-(1-((2-methoxyphenyl)amino)ethylidene)cyclohexane-1,3-dione 
• 1083067-06-4 2-amino-7-(4-fluoro-phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one O-(2-dimethylamino-ethyl)-oxime 
• 1083066-90-3 2-amino-7-(4-fluoro-phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one O-methyl-oxime 
• 1083066-89-0 2-amino-7-(4-fluoro-phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one oxime 
• 945298-72-6 2-amino-7-(4-fluoro-phenyl)-4-methyl-7,8-dihydro-6H-quinazolin-5-one 

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.

QUINAZOLIN-OXIME DERIVATIVES AS HSP90 INHIBITORS

Compounds of general formula (I); or a stereoisomers, tautomers, pharmaceutically acceptable salts, or prodrugs thereof, wherein R1, R2, R3, R4, R5, R6, R8 and R9 are as defined herein, are useful for the treatment of diseases and conditions which are mediated by excessive or inappropriate Hsp90 activity such as cancers, viral infection and inflammatory diseases or conditions.

COMPOUNDS AND METHODS FOR ALTERING LIFESPAN OF EUKARYOTIC ORGANISMS

Provided are compounds which generally have a triketone structure. Examples of the compounds include derivatives of 1,3-cyclohexanedione, such as: 1,3-cyclohexanedione, 2-propanoyl-5-cyclohexyl-; 1,3-cyclohexanedione, 2-propanoyl-5-[4-fluorophenyl]-; 1,3-cyclohexanedione, 2-acetyl-5-[thien-2-yl]-; 1,3-cyclohexanedione, 2-acetyl-5 -butyl-; and 1,3-cyclohexanedione, 2-propanoyl-5-[bicyclo[2.2.1]hept-2-en-5-yl]-. The compounds can be used to alter the lifespan of eukaryotic organisms and treat inflammation.