64603-74-3

Usage

Uses

Used in Pharmaceutical Research:
Methyl 2-methyl-4-(3-nitrophenyl)-5-oxo-5,7-dihydrofuro[3,4-b]pyridine-3-carboxylate is used as a research compound for exploring its biological activity and potential therapeutic effects. Its unique structure and functional groups may allow it to interact with biological targets, offering opportunities for the development of new drugs or therapeutic agents.
Used in Drug Development:
In the field of drug development, methyl 2-methyl-4-(3-nitrophenyl)-5-oxo-5,7-dihydrofuro[3,4-b]pyridine-3-carboxylate may serve as a lead compound or a structural template for designing new pharmaceuticals. Its chemical properties and potential interactions with biological systems could be harnessed to create novel drugs with specific therapeutic applications.

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 
• 39562-70-4 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridine-dicarboxylic acid ethyl methyl ester 
• 99-61-6 3-nitro-benzaldehyde 
• 14205-39-1 methyl (E)-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 
• 14205-39-1 methyl 3-aminocrotonate 
• 89267-46-9 3-ethyl-5-methyl-2-acetoxymethyl-6-methyl-4-(3-nitrophenyl)1,4-dihydropyridine-3,5-dicarboxylate 
• 107812-63-5 2-chloromethyl-3-carboethoxy-5-carbomethoxy-4-(m-nitro-phenyl)-6-methyl-1,4-dihydropyridine 

Relevant academic research and scientific papers

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.

Organic nitrates. II. Synthesis and biological activities of 4-nitrooxymethylphenyl-1,4-dihydropyridines.

Both 2-nitrooxymethyl-4-phenyl- (2) and 4-nitrooxymethylphenyl-1,4-dihydropyridines (3) represent new combinations of two different vasodilating structures. 2 could not be isolated due to its spontaneous lactonization. Derivatives of 3 were obtained via Hantzsch synthesis using nitrooxymethylated benzaldehydes. The inotropic potency in isolated porcine trabecular muscles and the vasodilator activity in isolated porcine coronary arteries of four nitrooxyphenyl-dihydropyridines were determined. Nitrendipine (NTD) and glyceryl trinitrate (GTN) were used for reference. 3 were negative inotropic, however, less than NTD and--except for the dicyano derivative 3d--more than GTN. Vasodilator properties were less pronounced than that of both nitrendipine and GTN. Vascular selectivity was low.

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