477933-12-3

Basic information

• Product Name: 1-(2-CYCLOPROPYL-ETHYL)-6-FLUORO-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE
• Synonyms: 1-(2-CYCLOPROPYL-ETHYL)-6-FLUORO-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE;1-(2-Cyclopropylethyl)-6-fluoro-2H-3,1-benzoxazine-2,4(1H)-dione;1-(2-Cyclopropylethyl)-6-fluorobenzo[d][1,3]oxazine-2,4-dione;2H-3,1-Benzoxazine-2,4(1H)-dione, 1-(2-cyclopropylethyl)-6-fluoro-
• CAS NO: 477933-12-3
• Molecular Formula: C13H12FNO3
• Molecular Weight: 249.24
• Product Categories: Aromatics;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 477933-12-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1-(2-CYCLOPROPYL-ETHYL)-6-FLUORO-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-CYCLOPROPYL-ETHYL)-6-FLUORO-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE(477933-12-3)
• EPA Substance Registry System: 1-(2-CYCLOPROPYL-ETHYL)-6-FLUORO-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE(477933-12-3)

Safety Data

• Hazardous Substances Data: 477933-12-3(Hazardous Substances Data)

Usage

Chemical Properties

Colorless Oil

Uses

Intermediate in the synthesis of HCV polymerase inhibitors.

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 477932-69-7 C₁₂H₁₄FNO₂ 
• 446-08-2 2-amino-5-fluorobenzoic acid 
• 321-69-7 5-fluoroisatoic anhydride 
• 2566-44-1 1-cyclopropylethanol 

Downstream Products

• 931399-20-1 ethyl 1-(2-cyclopropylethyl)-6-fluoro-4-hydroxy-2-oxo-1,2-dihydro-3-quinolinecarboxylate 

Relevant articles and documents

Non-nucleoside inhibitors of HCV NS5B polymerase. Part 1: Synthetic and computational exploration of the binding modes of benzothiadiazine and 1,4-benzothiazine HCV NS5b polymerase inhibitors

The importance of internal hydrogen bonding in a series of benzothiadiazine and 1,4-benzothiazine NS5b inhibitors has been explored. Computational analysis has been used to compare the protonated vs. anionic forms of each series and we demonstrate that activity against HCV NS5b polymerase is best explained using the anionic forms. The syntheses and structure-activity relationships for a variety of new analogs are also discussed.

3-(1,1-dioxo-2H-(1,2,4)-benzothiadiazin-3-yl)-4-hydroxy-2(1H)-quinolinones, potent inhibitors of hepatitis C virus RNA-dependent RNA polymerase

Recently, we disclosed a new class of HCV polymerase inhibitors discovered through high-throughput screening (HTS) of the GlaxoSmithKline proprietary compound collection. This interesting class of 3-(1,1-dioxo-2H-1,2,4- benzothiadiazin-3-yl)-4-hydroxy-2(1H)-quinolinones potently inhibits HCV polymerase enzymatic activity and inhibits the ability of the subgenomic HCV replicon to replicate in Huh-7 cells. This report will focus on the structure-activity relationships (SAR) of substituents on the quinolinone ring, culminating in the discovery of 1-(2-cyclopropylethyl)-3-(1,1-dioxo-2H-1,2,4- benzothiadiazin-3-yl)-6-fluoro-4-hydroxy-2(1H)-quinolinone (130), an inhibitor with excellent potency in biochemical and cellular assays possessing attractive molecular properties for advancement as a clinical candidate. The potential for development and safety assessment profile of compound 130 will also be discussed.