477-89-4

Basic information

• Product Name: CASIMIROIN
• Synonyms: CASIMIROIN;6-Methoxy-9-methyl-1,3-dioxolo[4,5-h]quinolin-8(9H)-one
• CAS NO: 477-89-4
• Molecular Formula: C₁₂H₁₁NO₄
• Molecular Weight: 233.22
• Mol File: 477-89-4.mol

Chemical Properties

• Melting Point: 203°
• Boiling Point: 375.46°C (rough estimate)
• Flash Point: 182°C
• Appearance: /
• Density: 1.2697 (rough estimate)
• Vapor Pressure: 6.81E-06mmHg at 25°C
• Refractive Index: 1.5560 (estimate)
• PKA: 0.08±0.40(Predicted)
• CAS DataBase Reference: CASIMIROIN(CAS DataBase Reference)
• NIST Chemistry Reference: CASIMIROIN(477-89-4)
• EPA Substance Registry System: CASIMIROIN(477-89-4)

Safety Data

• Hazardous Substances Data: 477-89-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H11NO4/c1-13-10(14)5-9(15-2)7-3-4-8-12(11(7)13)17-6-16-8/h3-5H,6H2,1-2H3

Upstream product

• 477-34-9 6-hydroxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 477-95-2 6-ethoxy-9-methyl-9H-[1,3]dioxolo[4,5-h]quinolin-8-one 
• 90049-79-9 4-isocyanato-benzo[1,3]dioxole 
• 96117-24-7 6-ethoxy-9H-[1,3]dioxolo[4,5-h]quinolin-8-one 
• 186581-53-3 diazomethane 

Downstream Products

• 115164-34-6 9-methyl-8,9-dihydro-7H-[1,3]dioxolo[4,5-h]quinolin-6-one 
• 111412-02-3 7-(4-methoxy-benzylidene)-9-methyl-8,9-dihydro-7H-[1,3]dioxolo[4,5-h]quinolin-6-one 

Relevant articles and documents

Synthesis of carbon-11-labeled casimiroin analogues as new potential PET agents for imaging of quinone reductase 2 and aromatase expression in breast cancer

Carbon-11-labeled casimiroin analogues were first designed and synthesized as new potential PET agents for imaging of quinone reductase (QR) 2 and aromatase expression in breast cancer. [11C]casimiroin (6-[ 11C]methoxy-9-methyl-[1,3]dioxolo[4,5-h]quinolin-8(9H)-one, [ 11C]11) and its carbon-11-labeled analogues 5,6,8-trimethoxy-1-[ 11C]methyl-4-methylquinolin-2(1H)-one ([11C]17), 8-methoxy-1-[11C]methyl-4-methylquinolin-2(1H)-one ([ 11C]21a), 6,8-dimethoxy-1-[11C]methyl-4-methylquinolin- 2(1H)-one ([11C]21b), and 5,8-dimethoxy-1-[11C]methyl-4- methylquinolin-2(1H)-one ([11C]21c), were prepared from their corresponding precursors with [11C]methyl triflate ([ 11C]CH3OTf) under basic conditions (NaH) through either O- or N-[11C]methylation and isolated by semi-preparative HPLC method in 40-50% radiochemical yields decay corrected to end of bombardment (EOB), based on [11C]CO2, and 111-185 GBq/μmol specific activity at the end of synthesis (EOS).

Synthesis of casimiroin and optimization of its quinone reductase 2 and aromatase inhibitory activities

An efficient method has been developed to synthesize casimiroin (1), a component of the edible fruit of Casimiroa edulis, on a multigram scale in good overall yield. The route was versatile enough to provide an array of compound 1 analogues that were evaluated as QR2 and aromatase inhibitors. In addition, X-ray crystallography studies of QR2 in complex with compound 1 and one of its more potent analogues has provided insight into the mechanism of action of this new series of QR2 inhibitors. The initial biological investigations suggest that compound 1 and its analogues merit further investigation as potential chemopreventive or chemotherapeutic agents.