64603-74-3

Basic information

• Product Name: methyl 2-methyl-4-(3-nitrophenyl)-5-oxo-5,7-dihydrofuro[3,4-b]pyridine-3-carboxylate
• Synonyms: methyl 2-methyl-4-(3-nitrophenyl)-5-oxo-5,7-dihydrofuro[3,4-b]pyridine-3-carboxylate;Furo[3,4-b]pyridine-3-carboxylic acid, 5,7-dihydro-2-methyl-4-(3-nitrophenyl)-5-oxo-, methyl ester
• CAS NO: 64603-74-3
• Molecular Formula: C₁₆H₁₂N₂O₆
• Molecular Weight: 328.2763
• Mol File: 64603-74-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 582.9°C at 760 mmHg
• Flash Point: 306.3°C
• Density: 1.423g/cm³
• Vapor Pressure: 1.42E-13mmHg at 25°C
• Refractive Index: 1.623
• CAS DataBase Reference: methyl 2-methyl-4-(3-nitrophenyl)-5-oxo-5,7-dihydrofuro[3,4-b]pyridine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-methyl-4-(3-nitrophenyl)-5-oxo-5,7-dihydrofuro[3,4-b]pyridine-3-carboxylate(64603-74-3)
• EPA Substance Registry System: methyl 2-methyl-4-(3-nitrophenyl)-5-oxo-5,7-dihydrofuro[3,4-b]pyridine-3-carboxylate(64603-74-3)

Safety Data

• Hazardous Substances Data: 64603-74-3(Hazardous Substances Data)

Usage

General Description

Methyl 2-methyl-4-(3-nitrophenyl)-5-oxo-5,7-dihydrofuro[3,4-b]pyridine-3-carboxylate is a chemical compound with a complex structure containing a furo[3,4-b]pyridine ring system. It is a ester derivative of a pyridine carboxylic acid, with a methyl group attached to the nitrogen of the pyridine ring and a nitrophenyl group attached to the carbon. methyl 2-methyl-4-(3-nitrophenyl)-5-oxo-5,7-dihydrofuro[3,4-b]pyridine-3-carboxylate may have biological activity and could potentially be used in pharmaceutical research or drug development. Its precise properties and potential uses would likely depend on its specific interactions with biological systems and its pharmacokinetic and pharmacodynamic profiles.

Upstream product

• 88250-01-5 methyl 2-methyl-4-(3-nitrophenyl)-5-oxo-1,4,5,7-tetrahydro-furo<3,4-b>pyridine-3-carboxylate 
• 14205-39-1 methyl 3-aminocrotonate 
• 76258-21-4 2,6-dimethyl-5-methoxycarbonyl-4-(m-nitrophenyl)pyridine-3-carboxylic acid N-oxide 
• 76258-20-3 Dimethyl 2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 
• 64603-72-1 SL 5721 
• 21881-77-6 m-nifedipine 
• 89267-46-9 3-ethyl-5-methyl-2-acetoxymethyl-6-methyl-4-(3-nitrophenyl)1,4-dihydropyridine-3,5-dicarboxylate 
• 99-61-6 3-nitro-benzaldehyde 
• 107812-63-5 2-chloromethyl-3-carboethoxy-5-carbomethoxy-4-(m-nitro-phenyl)-6-methyl-1,4-dihydropyridine 
• 14205-39-1 methyl (E)-3-aminocrotonate 
• 39562-70-4 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester 

Relevant articles and documents

3-(Nitrobenzylidene)-2,4(3H,5H)-furandiones in the Hantzsch pyridine synthesis, part 1.: A new approach to furo[3,4-b]pyridines

The nitrobenzylidenefurandiones 7 react with acetoacetic ester (8) and ammonium acetate or 3-aminocrotonic esters (9a, b) and 2-aminopent-2-en-4-on (9c), respectively heating in acetic acid to yield the tetrahydrofuro[3,4-b] pyridines 10. The dehydrogenation of 10 using nitric acid or activated manganese dioxide leads to the dihydrofuro[3,4-b]pyridines 12. When the reaction is carried out with the tetronic acid derivatives 7 and the enaminocarbonyl compounds 9 at 30°C in tert-butanol the hexahydro-7a-hydroxyfuro[3,4-b]pyridines 11 are obtained. Treating the N,O-acetales 11 with acetic anhydride in pyridine affords the annulated lactones 10.

Biotransformation of nitrendipine in rat, dog, and mouse

14C-Labelled Nitrendipine (Bay e 5009; Baypress, Bayotensin; CAS 39562-70-4) was administered by the oral and intraduodenal route to rats, dogs, and mice (oral dosing only) to elucidate the biotransformation pathways in these three species. The drug was extensively metabolized: 20 biotransformation products were identified by comparison with synthetic reference compounds using two-dimensional TLC, HPLC, GC/radio-GC, combined GC/MS (EI-, CI-mode), FAB-MS, and 1H-NMR-spectroscopy. The metabolites identified accounted for approx. 72 to 73% of the dose administered in rats and dogs (bile and urine) and 48 to 56% in male and female mice (urine only). Based on the structures identified the following biotransformation reactions occurred: Dehydrogenation of the 1,4-dihydropyridine (primary metabolic step), oxidative ester cleavage as further basic biotransformation reaction (also at the dihydropyridine state), hydroxylation of the methyl groups in 2- or 6-position as separated and important metabolic reaction (at the dihydropyridine as well as pyridine state), reduction of the aromatic nitro group (important only in mice) and subsequent acetylation (dog only), and glucuronidation as phase II reaction forming ether and ester type glucuronides.

Nitrendipine: Identification and synthesis of main metabolites

(±)-Ethylmethyl-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridined icarboxylate (nitrendipine, Baye e 5009) 1, a calcium antagonistic 1,4-dihydropyridine derivative, is currently under development as an antihypertensive. A pharmacokinetic study with