146698-91-1

Basic information

• Product Name: (E/Z)-3-O-Methyl Entacapone
• Synonyms: (E/Z)-3-O-Methyl Entacapone;(E/Z)-Entacapone 3-Methyl Ether;2-Cyano-N,N-diethyl-3-(4-hydroxy-3-Methoxy-5-nitrophenyl)-2-propenaMide
• CAS NO: 146698-91-1
• Molecular Formula: C₁₅H₁₇N₃O₅
• Molecular Weight: 319.31258
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 146698-91-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 514.1±50.0 °C(Predicted)
• Appearance: /
• Density: 1.304±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 5.67±0.50(Predicted)
• CAS DataBase Reference: (E/Z)-3-O-Methyl Entacapone(CAS DataBase Reference)
• NIST Chemistry Reference: (E/Z)-3-O-Methyl Entacapone(146698-91-1)
• EPA Substance Registry System: (E/Z)-3-O-Methyl Entacapone(146698-91-1)

Safety Data

• Hazardous Substances Data: 146698-91-1(Hazardous Substances Data)

Usage

Uses

Intermediate in the preparation of Entacapone (E558500).

Upstream product

• 6635-20-7 isonitrovanillin 
• 26391-06-0 2-cyano-N,N-diethylacetamide 

Downstream Products

• 130929-57-6 entacapone 
• 145195-63-7 (2Z)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide 

Relevant articles and documents

A new synthesis of Entacapone and report on related studies

A new synthesis of the catechol-O-methyltransferase (COMT) inhibitor, entacapone (E-isomer) has been achieved under mild conditions by amine-mediated demethylation of the precursor 2-Cyano-3-(3- hydroxy-4-methoxy-5-nitrophenyl) prop-2-eneamide, wherein the methoxyl group adjacent to a nitro group gets demethylated under nucleophilic attack. Similar demethylation was achieved on ethyl 2-cyano-3-(3, 4-dimethoxy-5-nitrophenyl) prop-2-enoate, 2-cyano-3-(3,4-dimethoxy-5-nitrophenyl)-N,N-diethylprop-2-enamide, ethyl 2-cyano-3-(3-hydroxy-4-methoxy-5-nitrophenyl) prop-2-enoate and ethyl 2-cyano-3-(4-methoxy-3-nitrophenyl) prop-2-enoate. The scope of demethylation has been studied. Analogues of ethyl 2-cyano-3-(3, 4-dimethoxy-5-nitrophenyl) prop-2-enoate wherein a methoxyl group is not adjacent to a NO 2 group are unaffected and phenolic derivatives yield the amine salts. Entacapone has been converted to salts with organic bases. The crystal structure of the isomer of entacapone (Z-isomer), a significant human metabolite of E-isomer has been established. NMR methods for deriving E and Z geometry and other similar molecules have been successfully established, mainly by studying the proton coupled 13C spectra. Preliminary studies reveal in vitro activity for some compounds against tuberculosis (TB) and dengue. [Figure not available: see fulltext.]

DENGUE AND WEST NILE VIRUS PROTEASE INHIBITORS

Compounds and methods of treating or preventing a Flavivirus infection in a subject are provided. The methods comprise administering to the subject a therapeutically effective amount of a compound as described herein. The methods are useful in treating and/or preventing Flavivirus infections such as, for example, West Nile Virus, Dengue Virus, and Japanese Encephalitis Virus. Methods of inhibiting a Flavivirus protease in a cell are also provided.