17844-66-5

Basic information

• Product Name: BICYCLOHEXYL-3,5-DIONE
• Synonyms: BICYCLOHEXYL-3,5-DIONE
• CAS NO: 17844-66-5
• Molecular Formula: C₁₂H₁₈O₂
• Molecular Weight: 222.24
• Mol File: 17844-66-5.mol

Chemical Properties

• Boiling Point: 333.1°C at 760 mmHg
• Flash Point: 124.9°C
• Appearance: /
• Density: 1.081g/cm³
• Vapor Pressure: 0.000139mmHg at 25°C
• Refractive Index: 1.509
• CAS DataBase Reference: BICYCLOHEXYL-3,5-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: BICYCLOHEXYL-3,5-DIONE(17844-66-5)
• EPA Substance Registry System: BICYCLOHEXYL-3,5-DIONE(17844-66-5)

Safety Data

• Hazardous Substances Data: 17844-66-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H18O2/c13-11-6-10(7-12(14)8-11)9-4-2-1-3-5-9/h9-10H,1-8H2

Upstream product

• 861618-55-5 3,5-dioxo-bicyclohexyl-2-carboxylic acid ethyl ester 
• 7152-32-1 4-cyclohexyl-3-buten-2-one 
• 105-53-3 diethyl malonate 
• 2043-61-0 cyclohexanecarbaldehyde 
• 1381884-63-4 (E)-5-cyclohexylpent-3-en-2-one 
• 141-52-6 sodium ethanolate 

Downstream Products

• 144128-85-8 7-Chloro-3-cyclohexyl-10-hydroxy-3,4-dihydro-2H,10H-acridine-1,9-dione 
• 1309249-98-6 1,3-cyclohexanedione, 2-propanoyl-5-cyclohexyl- 
• 1609374-91-5 4-(1-((2-methoxyphenyl)amino)ethylidene)-[1,1'-bi(cyclohexane)]-3,5-dione 

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.

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.

SUBSTITUTED DIHYDROPYRIDINES AND METHODS OF USE

Compounds are provided that are modulators of the C5a receptor. The compounds are substituted dihydropyridines and are useful in pharmaceutical compositions, methods for the treatment of diseases and disorders involving the pathologic activtation of C5a receptors.

Synthesis and Antimalarial Properties of 1-Imino Derivatives of 7-Chloro-3-substituted-3,4-dihydro-1,9(2H,10H)-acridinediones and Related Structures

To improve upon the activity and properties of the 3-aryl-7-chloro-3,4-dihydro-1,9(2H,10H)-acridinediones, a variety of 1-imino derivatives (3) were prepared and shown to be highly active antimalarial agents in both rodents and primates.Among structural modifications prepared, including N10-alkyl and C2-substituted analogs, removal of the C9 oxygen, and introduction of an imino side chain at C9, the imines of the N10-H acridinediones were the most active compounds obtained.The imino derivative of7-chloro-3-(2,4-dichlorophenyl)-3,4-dihydro-1,9(2H,10H)-acridinedione (9aa) proved to be highly active in advanced studies in primates.