89267-47-0

Upstream product

• 62760-94-5 diethyl-2-acetoxymethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 141-97-9 ethyl acetoacetate 
• 41867-20-3 ethyl (E)-3-aminobut-2-enoate 
• 99-61-6 3-nitro-benzaldehyde 
• 62760-70-7 diethyl 2-hydroxymethyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 626-34-6 ethyl aminocrotonate 
• 35594-15-1 ethyl 4-acetoxyacetoacetate 
• 204848-35-1 2-bromomethyl-3,5-dicarboethoxy-4-(3-nitrophenyl)-6-methyl-1,4-dihydropyridine 

Downstream Products

• 89288-25-5 ethyl-2-methyl-4-(3-nitrophenyl)-5-oxo-5,7-dihydrofuro<3,4-b>3-pyridinecarboxylate 

Relevant academic research and scientific papers

Synthesis of unsymmetrical 1, 4-dihydropyridine derivatives in ionic liquid and inference on the formation mechanism of furopyridines

Aromatic aldehydes, methyl acetoacetate, ethyl acetoacetate, ammonium acetate, ethyl 4-chloroacetoacetate as materials, eight unsymmetrical 1, 4-dihydropyridine derivatives were synthesized in ionic liquid [Bmim]OH in short time with the 60%-90% yield, and the ionic liquid could be utilized for 5 times repeatedly with the no decrease of the yield, four of products [3(a-d)] (see in Table-1) were synthesized through Knoevenagel and Michael addition reaction, and another four Furopyridines [3(e-h)] (see in Table-2) through one-pot synthesis whose formation mechanism being different from that of [3(a-d)] was first inferred.

Antagonism of 4-substituted 1,4-dihydropyridine-3,5-dicarboxylates toward voltage-dependent L-type Ca2+ channels CaV1.3 and CaV1.2

L-type Ca2+ channels in mammalian brain neurons have either a CaV1.2 or CaV1.3 pore-forming subunit. Recently, it was shown that CaV1.3 Ca2+ channels underlie autonomous pacemaking in adult dopaminergic neurons in the substantia nigra pars compacta, and this reliance renders them sensitive to toxins used to create animal models of Parkinson's disease. Antagonism of these channels with the dihydropyridine antihypertensive drug isradipine diminishes the reliance on Ca2+ and the sensitivity of these neurons to toxins, pointing to a potential neuroprotective strategy. However, for neuroprotection without an antihypertensive side effect, selective CaV1.3 channel antagonists are required. In an attempt to identify potent and selective antagonists of CaV1.3 channels, 124 dihydropyridines (4-substituted-1,4-dihydropyridine-3,5-dicarboxylic diesters) were synthesized. The antagonism of heterologously expressed CaV1.2 and CaV1.3 channels was then tested using electrophysiological approaches and the FLIPR Calcium 4 assay. Despite the large diversity in substitution on the dihydropyridine scaffold, the most CaV1.3 selectivity was only about twofold. These results support a highly similar dihydropyridine binding site at both CaV1.2 and CaV1.3 channels and suggests that other classes of compounds need to be identified for CaV1.3 selectivity.

Synthesis of novel asymmetrical 1,4-dihydropyridine derivatives

Asymmetrical 1,4-dihydropyridine esters 3a and 3i-k were synthesized from the symmetrical precursor 1 through the intermediate 2-bromomethyl derivative 2. Then, compound 3a was subjected to a different transformation for preparation of 1,4-dihydropyridine

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.

Circulation-active hydroxy-tetra-hydropyridinelactones

Hydroxytetrahydropyridinelactones of the formula STR1 in which R represents a phenyl, naphthyl, thienyl, furyl, pyrryl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidyl, pyrazinyl, quinolyl, isoquinolyl, indolyl, ben

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