61363-56-2

Usage

Uses

Used in Organic Synthesis:
PYRAN-3,5-DIONE is used as a building block in organic synthesis for its reactivity and ability to form a wide range of organic compounds.
Used in Pharmaceutical Industry:
PYRAN-3,5-DIONE is used as a precursor in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and agricultural products.
Used in Production of Synthetic Dyes and Perfumes:
PYRAN-3,5-DIONE is used in the production of synthetic dyes and perfumes, enhancing the color and fragrance properties of these products.
Used in Antioxidant and Anti-Inflammatory Applications:
PYRAN-3,5-DIONE is studied for its potential as an antioxidant and anti-inflammatory agent, offering promising therapeutic properties for various health conditions.

InChI:InChI=1/C8H4Cl2N2O/c9-4-1-2-6-5(3-4)7(13)12-8(10)11-6/h1-3H,(H,11,12,13)

Upstream product

• 61363-66-4 (2-oxopropoxy)acetic acid methyl ester 
• 67500-49-6 methyl 2-(prop-2-yn-1-yloxy)acetate 
• 10041-27-7 [(2-methylprop-2-en-1-yl)oxy]acetic acid 
• 137840-76-7 methyl [(2-methylprop-2-en-1-yl)oxy]acetate 

Downstream Products

• 688785-30-0 5-ethoxy-2H-pyran-3(6H)-one 
• 927670-52-8 4-(3-bromo-4-methyl-phenyl)-2-butyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylic acid ethyl ester 
• 927670-37-9 2-butyl-4-(3-chloro-4-fluoro-phenyl)-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylic acid ethyl ester 
• 927670-48-2 2-butyl-4-(3,4-dibromo-phenyl)-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylic acid ethyl ester 
• 927670-47-1 4-(4-bromo-3-chloro-phenyl)-2-butyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylic acid ethyl ester 
• 927670-46-0 4-(3-bromo-4-chloro-phenyl)-2-butyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylic acid ethyl ester 
• 497098-26-7 methyl 2-ethyl-4-(4-fluoro-3-iodophenyl)-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridin-3-carboxylate 
• 372120-75-7 4-(3-bromo-4-fluorophenyl)-2-isopropyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylic acid ethyl ester 
• 927664-88-8 4-(3-bromo-4-fluoro-phenyl)-2-isobutyl-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylic acid methyl ester 
• 927663-90-9 4-(3-bromo-4-fluoro-phenyl)-2-(2-methoxy-ethyl)-5-oxo-4,5,6,8-tetrahydro-1H-pyrano[3,4-b]pyridine-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Highly potent HIV-1 protease inhibitors with novel tricyclic P2 ligands: Design, synthesis, and protein-ligand X-ray studies

The design, synthesis, and biological evaluation of a series of HIV-1 protease inhibitors incorporating stereochemically defined fused tricyclic P2 ligands are described. Various substituent effects were investigated to maximize the ligand-binding site interactions in the protease active site. Inhibitors 16a and 16f showed excellent enzyme inhibitory and antiviral activity, although the incorporation of sulfone functionality resulted in a decrease in potency. Both inhibitors 16a and 16f maintained activity against a panel of multidrug resistant HIV-1 variants. A high-resolution X-ray crystal structure of 16a-bound HIV-1 protease revealed important molecular insights into the ligand-binding site interactions, which may account for the inhibitor's potent antiviral activity and excellent resistance profiles.

An improved synthesis of Pyran-3,5-dione: Application to the synthesis of ABT-598, a potassium channel opener, via Hantzsch reaction

Ketoester 1 is cyclized to give pyran-3,5-dione 2 in 78% yield using a parallel addition of ketoester 1 and base NaOtBu in refluxing THF. Compared to the previously reported procedures, these optimized conditions have significantly increased the yield of this transformation and the quality of pyran 2 and prove to be suitable for large-scale preparation. An application of 2 to the synthesis of ABT-598, a potassium channel opener, is demonstrated.

Effects of substitution on 9-(3-bromo-4-fluorophenyl)-5,9-dihydro-3H,4H-2, 6-dioxa-4-azacyclopenta[b]naphthalene-1,8-dione, a dihydropyridine ATP-sensitive potassium channel opener

Structure-activity relationships were investigated on the tricyclic dihydropyridine (DHP) KATP openers 9-(3-bromo-4-fluorophenyl)-5,9-dihydro-3H,4H- 2,6-dioxa-4-azacyclopenta[b]naphthalene-1,8-dione (6) and 10-(3-bromo-4- fluorophenyl)-9,10-dihydro-1H,8H-2,7-dioxa-9-azaanthracene-4,5-dione (65). Substitution off the core of the DHP, absolute stereochemistry, and aromatic substitution were evaluated for KATP channel activity using Ltk- cells stably transfected with the Kir6.2/SUR2B exon 17- splice variant and in an electrically stimulated pig bladder strip assay. A select group of compounds was evaluated for in vitro inhibition of spontaneous bladder contractions. Several compounds were found to have the unique characteristic of partial efficacy in both the cell-based and electrically stimulated bladder strip assays but full efficacy in inhibiting spontaneous bladder strip contractions. For compound 23b, this profile was mirrored in vivo where it was fully efficacious in inhibiting spontaneous myogenic bladder contractions but only partially able to reduce neurogenically mediated reflex bladder contractions.

5-Amino-2H-pyran-3(6H)-one, 1, a Convenient Intermediate in the Synthesis of Pyran Containing 1,4-Dihydropyridines

5-Amino-2H-pyran-3(6H)-one, 1, is a novel intermediate that is useful in the synthesis of pyran containing dihydropyridines. The synthesis and use of 1 will be discussed.

Pyrano, piperidino, and thiopyrano compounds and methods of use

The present invention provides novel compounds of formula I which may be useful in hyperpolarizing cell membranes, opening potassium channels, relaxing smooth muscle cells, and inhibiting bladder contractions.

Novel radioligands and their use for identifying potassium channel modulators

The present invention relates to novel radioligands and test methods using those radioligands in screening compounds.

Pyrano, piperidino, and thiopyrano compounds and methods of use

The present invention provides novel compounds of formula I which may be useful in hyperpolarizing cell membranes, opening potassium channels, relaxing smooth muscle cells, and inhibiting bladder contractions.