41479-98-5

Upstream product

• 53063-63-1 5-hydroxy-3-oxo-5-phenyl-valeric acid methyl ester 
• 5764-85-2 Ethyl 3-hydroxy-3-phenylpropanoate 
• 100-52-7 benzaldehyde 
• 105-45-3 acetoacetic acid methyl ester 

Downstream Products

• 1020850-69-4 trifluoromethanesulfonic acid 6-oxo-2-phenyl-3,6-dihydro-2H-pyran-4-yl ester 
• 1312921-06-4 C₁₅H₁₇NO₅ 
• 17298-18-9 4-methoxy-6-phenyl-5,6-dihydro-pyran-2-one 
• 99275-23-7 4-p-toluenesulfonyloxy-6-phenyl-5,6-dihydro-2H-pyran-2-one 

Relevant academic research and scientific papers

Identification of 3,6-disubstituted dihydropyrones as inhibitors of human lactate dehydrogenase

A series of 3,6-disubstituted dihydropyrones were identified as inhibitors of human lactate dehydrogenase (LDH)-A. Structure activity relationships were explored and a series of 6,6-spiro analogs led to improvements in LDHA potency (IC50 50 = 30 nM).

A rapid and diverse construction of 6-substituted-5,6-dihydro-4-hydroxy-2- pyrones through double Reformatsky reaction

A rapid and diverse synthesis of biologically important 6-substituted-5,6-dihydro-4-hydroxy-2-pyrones through a double Reformatsky reaction of aldehydes to δ-hydroxy-β-ketoesters followed by lactonization is described. Due to the high functional group tolerance and reaction site discrimination between aldehyde, nitrile, and ester groups in the substrate, the protocol can provide the dihydropyrones with bromo, nitro, carboxylic acid, and β-ketoester groups, which are suitable for the further derivatizations. Furthermore, the protocol has been successfully applied to the rapid total synthesis of naturally occurring Yangonin.

INHIBITORS OF UNDECAPRENYL PYROPHOSPHATE SYNTHASE

The present invention relates to compounds that are selective and/or potent inhibitors of UPPS. In addition to compounds which inhibit UPPS, the invention also provides pharmaceutical compositions comprising these compounds and methods of using these comp

Synthesis and in vitro studies of pyrone derivatives as scavengers of active oxygen species

The antioxidant properties of eleven αpyrones and four γ-pyrones were evaluated by means of three different tests: reduction of the stable free radical, 1,1-diphenyl-2-picrylhydrazyl (DPPH), superoxide anion scavenging assay and lipid peroxidation assay. In the DPPH test, 6-aryl-5,6-dihydro-4-hydroxypyran2-ones (3) and 4-hydroxypyran-2-one (5f) were the most active derivatives with IC50 values ranging from 36.7 to 394 μmol/1. Potent superoxide anion scavenging properties appeared in derivatives possessing phenol moieties. Thus phenolic pyrones 5e and 5f exhibited a note- worthy activity (IC50 = 0.180 and 0.488 mmol/l, respectively) when reference compound, ascorbic acid, demonstrated only 24 % inhibition at a concentration of 1 mg/ml. In addition derivative 5f significantly inhibited the Fe2+/ADP/ascorbate-induced lipid peroxidation of rat liver microsomes with an IC50 value of 0.069 mmol/l. Due to its multiple mechanism of protective action, compound 5f may be useful for the treatment of oxidative tissue injury in human disease.

5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents

The present invention relates to novel 5,6-dihydropyrone derivatives and related structures which potently inhibit the HIV aspartyl protease blocking HIV infectivity. The 5,6-dihydropyrone derivatives are useful in the development of therapies for the tre

5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents

The present invention relates to novel 5,6-dihydropyrone derivatives and related structures which potently inhibit the HIV aspartyl protease blocking HIV infectivity. The 5,6-dihydropyrone derivatives are useful in the development of therapies for the tre

4-hydroxy-5,6-dihydropyrones. 2. Potent non-peptide inhibitors of HIV protease

The 4-hydroxy-5,6-dihydropyrone template was utilized as a flexible scaffolding from which to build potent active site inhibitors of HIV protease. Dihydropyrone 1c (5,6-dihydro-4-hydroxy-6-phenyl-3-[(2- phenylethyl)thio]-2H-pyran-2-one) was modeled in the active site of HIV protease utilizing a similar binding mode found for the previously reported 4-hydroxybenzopyran-2-ones. Our model led us to pursue the synthesis of 6,6- disubstituted dihydropyrones with the aim of filling S1 and S2 and thereby increasing the potency of the parent dihydropyrone 1c which did not fill S2. Toward this end we attached various hydrophobic and hydrophilic side chains at the 6-position of the dihydropyrone to mimic the natural and unnatural amino acids known to be effective substrates at P2 and P2'. Parent dihydropyrone 1c (IC50 = 2100 nM) was elaborated into compounds with greater than a 100-fold increase in potency [18c, IC50 = 5 nM, 5-(3,6- dihydro-4-hydroxy-6-oxo-2-phenyl-5-[2-phenylethyl)thio]-2H-pyran-2- yl)pentanoic acid and 12c, IC50 = 51 nM, 5,6-dihydro-4-hydroxy-6-phenyl-6- (2-phenylethyl)-3-[(2-phenyl-ethyl)thio]-2H-pyran-2-one]. Optimization of the 3-position fragment to fill S1' and S2' afforded potent HIV protease inhibitor 49 [IC50 = 10 nM, 3-[(2-tert-butyl-5-methylphenyl)sulfanyl]-5,6- dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one]. The resulting low molecular weight compounds (475) have one or no chiral centers and are readily synthesized.

EFFICACIOUS ENTRY INTO SUBSTITUTED 5,6-DIHYDRO-4-HYDROXY-2H-PYRAN-2-ONES AND 2,3-DIHYDRO-4H-PYRAN-4-ONES UTILIZING KETONIC DIANIONS

Methyl acetoacetate and 2,4-pentanedione dianions were condensed with aldehydes and ketones to afford a 1,3,5-trioxygenated carboskeleton.Intramolecular cyclization of the aldol adducts delivered the title compounds in good yield.