725-92-8

Usage

InChI:InChI=1/C11H12O6/c1-3-15-10(13)8-5-7(12)6-9(17-8)11(14)16-4-2/h5-6H,3-4H2,1-2H3

Upstream product

• 68854-18-2 2,4,6-trioxo-heptanedioic acid diethyl ester 
• 99-32-1 chelidonic acid 
• 64-17-5 ethanol 
• 7647-01-0 hydrogenchloride 
• 67-64-1 acetone 
• 95-92-1 oxalic acid diethyl ester 

Downstream Products

• 717-72-6 6-(ethoxycarbonyl)-4-oxo-4H-pyran-2-carboxylic acid 
• 97941-75-8 1-(3-hydroxy-phenyl)-4-oxo-1,4-dihydro-pyridine-2,6-dicarboxylic acid diethyl ester 
• 97941-87-2 diethyl 1-(p-hydroxyphenyl)chelidamate 
• 5909-20-6 4-(2,4,6-trioxo-1-phenyl-tetrahydro-pyrimidin-5-ylidene)-4H-pyran-2,6-dicarboxylic acid diethyl ester 
• 5900-33-4 4-(4,6-dioxo-1,3-diphenyl-2-thioxo-tetrahydro-pyrimidin-5-ylidene)-4H-pyran-2,6-dicarboxylic acid diethyl ester 
• 339998-00-4 diethyl 1-(o-hydroxyphenyl)chelidamate 
• 1192159-36-6 diethyl 2-nitro-5-hydroxyisophthalate 
• 1192159-40-2 diethyl 2-acetyl-5-hydroxyisophthalate 
• 854835-74-8 1-(3-hydroxy-phenyl)-4-oxo-1,4-dihydro-pyridine-2,6-dicarboxylic acid 
• 854835-73-7 1-(4-hydroxy-phenyl)-4-oxo-1,4-dihydro-pyridine-2,6-dicarboxylic acid 
• 97941-79-2 6,8-Dioxo-5-phenylamino-6,8-dihydro-5H-pyrido[1,2-a]quinoxaline-10-carboxylic acid N'-phenyl-hydrazide 
• 97941-78-1 5-Benzyl-6,8-dioxo-6,8-dihydro-5H-pyrido[1,2-a]quinoxaline-10-carboxylic acid benzylamide 

Relevant academic research and scientific papers

NOVEL DUAL MODE OF ACTION SOLUBLE GUANYLATE CYCLASE ACTIVATORS AND PHOSPHODIESTERASE INHIBITORS AND USES THEREOF

The present invention relates to compounds of formula (I), or pharmaceutically acceptable salt, solvate or hydrate thereof, wherein said compound of formula (I) comprises at least one covalently bound -ONO2 or -ONO moiety and at most four covalently bound -ONO2 or -ONO moieties, and wherein AR, R1, X, R3 and R4 are as defined in claim 1; and pharmaceutical compositions thereof, and their use in methods of treating or preventing a disease alleviated by inhibition of PDE5 in a human or in a non-human mammal.

New series of γ-pyrone based podands: Synthesis, characterization and study of their application in acetate salts cation trapping for nucleophilic substitution reactions

Dialkyl 4-oxo-4H-pyran-2,6-dicarboxylates are synthesized via esterification of chelidonic acid or via intramolecular cyclization of dialkyl-2,4,6-trioxoheptanedioates. Reaction of the dialkyl 4-oxo-4H-pyran-2,6-dicarboxylates with a variety of glycol monoalkyl ethers produces a series of new podands in good yields. To demonstrate the use of these podands in cation trapping, nucleophilic substitution reactions are carried out with various acetate salts. The results indicate that the cation diameter’s compatibility with binding site leads to the best yield of reaction.

The synthesis of substituted phenols from pyranone precursors

The syntheses of various substituted phenols from pyranone precursors, namely 4H-pyran-4-one, 3-(benzyloxy)-2-methyl-4H-pyran-4-one (benzyl-maltol), 2,6-dimethyl-4H-pyran-4-one and diethyl 4-oxo-4H-pyran-2,6-dicarboxylate (diethyl chelidonate) are presented. A variety of pronucleophiles were used in combination with tert-butanol as solvent and potassium tert-butoxide as base, using conventional heating methods and microwave conditions.

The chemistry of the highly reactive 2,6-bis(bromomethyl)-4-pyrone

Under basic conditions 2,6-bis(bromomethyl)-4-pyrone 8 reacts with tetraethylene glycol to yield the unexpected macrocycle 9, which is related to the antibiotic Kjellmanianone 10. We propose that this ring transformation proceeds via the cyclopropyl inter

Chelidonic acid as precursor for 2,5-desoxy-c-glycosides

Diethyl chelidonate (1) was converted by 5 convenient steps into the 2,4,6-trifunctionalized tetrahydropyran (6), which is a key intermediate for natural products and peptide turn mimetics. The important all syn- configuration was achieved by catalytic hydrogenation.

Enzymatic desymmetrization of meso cis,cis-2,4,6-substituted tetrahydropyrans

The stereoselective acylation of meso-tetrahydropyrans 6 and 7 by enol esters (vinyl acetate or isopropenyl acetate) in the presence of Candida antarctica lipase in organic media gave the corresponding (2R,4S,6S)- monoesters 10 and 11 in high enantiomeric purity. The hydrolysis of the corresponding diacetate derivatives 8 and 9 in the presence of the same enzyme provided the opposite enantiomers, (2S,4R,6R)-monoesters 10 and 11.