5526-38-5

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 31, p. 1032, 1966 DOI: 10.1021/jo01342a010

Upstream product

• 5526-43-2 5-phenyl-3,5-dioxo-1-pentanoic acid 
• 86969-12-2 α-benzoylacetoacetic acid ethyl ester 
• 115411-39-7 methyl 4-hydroxy-2-oxo-6-phenyl-2H-pyran-3-carboxylate 
• 530-62-1 1,1'-carbonyldiimidazole 
• 4071-85-6 trimetylsilylketene 
• 55991-67-8 5-phenylfuran-2,3-dione 
• 71-43-2 benzene 
• 614-20-0 3-oxo-3-phenylpropionic acid 
• 100-52-7 benzaldehyde 
• 25718-12-1 C₂₈H₄₀N₇O₁₇P₃S 
• 36568-12-4 methyl 3,5-dioxo-5-phenylpentanoate 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 1663-67-8 malonoyl dichloride 
• 136801-74-6 2,2-dimethyl-6-(2-oxo-2-phenylethyl)-4H-1,3-dioxin-4-one 

Downstream Products

• 126713-49-3 1-phenyl-3,5,9,11-tetraoxo-4,10-dioxy-14-methoxy-2,6,7,8,12-cis-<5.5.2.0.^2,6.0^8,12>pentacyclotetradec-13-ene 
• 126713-48-2 3,5,9,11-tetraoxo-1,4,10-triphenyl-4,10-diaza-14-methoxy-2,6,7,8,12-cis-<5.5.2.0.^2,6.0^8,12>pentacyclotetradec-13-ene 
• 170913-58-3 3-[2-Cyclohexyl-1-(phenylthio)ethyl]-4-hydroxy-6-phenyl-2H-pyran-2-one 
• 170914-23-5 3-[1-[(Cyclohexylmethyl)thio]phenylmethyl]-4-hydroxy-6-phenyl-2H-pyran-2-one 

Relevant academic research and scientific papers

The Botrytis cinerea type III polyketide synthase shows unprecedented high catalytic efficiency toward long chain acyl-CoAs

BPKS from Botrytis cinerea is a novel type III polyketide synthase that accepts C4-C18 aliphatic acyl-CoAs and benzoyl-CoA as the starters to form pyrones, resorcylic acids and resorcinols through sequential condensation with malonyl-CoA. The catalytic efficiency (kcat/K m) of BPKS was 2.8 × 105 s-1 M -1 for palmitoyl-CoA, the highest ever reported. Substrate docking analyses addressed the unique features of BPKS such as its high activity and high specificity toward long chain acyl-CoAs.

Nonpeptidic potent HIV-1 protease inhibitors: (4-hydroxy-6-phenyl-2-oxo- 2H-pyran-3-yl)thiomethanes that span P1-P2' subsites in a unique mode of active site binding

Using molecular modeling and the information derived from the X-ray crystal structure of HIV-1 protease (HIV PR) complexed with the pyran-2-one l, a series of (4-hydroxy-6-phenyl-2-oxo-2H-pyran-3-yl)thiomethanes was designed and analyzed as novel, nonpept

Synthesis and antimicrobial activity of new prenylated 2-pyrone derivatives

A series of new monoprenylated and diprenylated 2-pyrone derivatives with different halogen substituents were synthesized from the corresponding 6-aryl-4-hydroxy-2-pyrones by prenylation reactions. The compounds were evaluated for antibacterial activity and displayed significant in vitro activity with the highest activity shown by the monoprenylated 6-aryl-2-pyrones. All the compounds except the bromine-containing analogs were active against one or more tested bacteria, with Escherichia coli being the most susceptible of the test organisms. With the remarkable antibacterial activity of eight of the compounds against a drug-resistant β-lactamase-producing Klebsiella pneumoniae, a synergistic evaluation between each of these compounds and ampicillin was undertaken. Out of the eight combinations studied, synergistic effects were observed with two compounds, 4-(3-methylbut-2-enoxy)-6-phenyl-2H-pyran-2-one and 6-(4-fluorophenyl)-4-(3-methylbut-2-enoxy)-2H-pyran-2-one. Both compounds, at half the individual MIC values, were able to lower the MIC of ampicillin in combinations from 2500 to 2.4 μg/mL (1/1041 of MIC).

NEW ANTIBACTERIAL COMPOUNDS

The present invention relates to novel antibacterial compounds, pharmaceutical compositions containing them and their use as antimicrobials.

Gold- or Silver-Catalyzed Syntheses of Pyrones and Pyridine Derivatives: Mechanistic and Synthetic Aspects

3-Oxo-5-alkynoic acid esters, on treatment with a carbophilic catalyst, undergo 6-endo-dig cyclization reactions to furnish either 2-pyrones or 4-pyrones in high yields. The regiochemical course can be dialed in by the proper choice of the alcohol part of the ester and the π-acid. This transformation is compatible with a variety of acid-sensitive groups as witnessed by a number of exigent applications to the total synthesis of natural products, including pseudopyronine A, hispidine, phellinin A, the radininol family, neurymenolide, violapyrone, wailupemycin and an unnamed brominated 4-pyrone of marine origin. Although the reaction proceeds well in neutral medium, the rate is largely increased when HOAc is used as solvent or co-solvent, which is thought to favor the protodeauration of the reactive alkenyl-gold intermediates as the likely rate-determining step of the catalytic cycle. Such intermediates are prone to undergo diauration as an off-cycle event that sequesters the catalyst; this notion is consistent with literature data and supported by the isolation of the gem-diaurated complexes 12 and 15. Furthermore, silver catalysis allowed access to be gained to 2-alkoxypyridine and 2-alkoxyisoquinoline derivatives starting from readily available imidate precursors.

Pd-catalysed intramolecular regioselective arylation of 2-pyrones, pyridones, coumarins and quinolones by C–H bond functionalization

The intramolecular arylation of 2-pyrones, 2-pyridones, coumarins and quinolones is reported using PdII precatalyst sources without added phosphine ligands. The excellent yields and convenient reagents enables the formation of various analogues

Cloning and structure-function analyses of quinolone- and acridone-producing novel type III polyketide synthases from citrus microcarpa

Background:Type III polyketide synthases (PKSs) synthesize various polyketide and alkaloid scaffolds. Results:QNS synthesizes quinolone as the single product, whereas ACS produces acridone as the major product. Conclusion:QNS and ACS are novel quinolone- and acridone-producing type III PKSs, respectively. Significance:Structure-function analyses of QNS and ACS provide insights into molecular bases for alkaloid biosyntheses.

A type III polyketide synthase from Rhizobium etli condenses malonyl CoAs to a heptaketide pyrone with unusually high catalytic efficiency

A novel type III polyketide synthase (RePKS) from Rhizobium etli produced a heptaketide pyrone using acetyl-CoA and six molecules of malonyl-CoA. Its catalytic efficiency (kcat/Km = 5230 mM-1 min-1) for malonyl CoA was found to be the highest ever reported. Molecular dynamics studies revealed the unique features of RePKS. The Royal Society of Chemistry 2012.

Total synthesis of neurymenolide-A Based on a gold-catalyzed synthesis of 4-hydroxy-2-pyrones

Treat me gently: For a selective synthesis of the unusually sensitive cyclophanic α-pyrone neurymenolide A, the chosen catalysts must be able to distinguish between six different sites of unsaturation, without scrambling any of the skipped π systems. This challenge was met with a new gold-catalyzed pyrone synthesis in combination with a molybdenum-catalyzed ring-closing alkyne metathesis. Copyright

Antitumor agents 287. Substituted 4-amino-2H-pyran-2-one (APO) analogs reveal a new scaffold from neo-tanshinlactone with in vitro anticancer activity

4-Amino-2H-benzo[h]chromen-2-one (ABO) and 4-amino-7,8,9,10-tetrahydro-2H- benzo[h]chromen-2-one (ATBO) analogs were found to be significant in vitro anticancer agents in our previous research. Our continuing study has now discovered a new simplified (monocyclic rather than tricyclic) class of cytotoxic agents, 4-amino-2H-pyran-2-one (APO) analogs. By incorporating various substituents on the pyranone ring, we have established preliminary structure-activity relationships (SAR). Analogs 19, 20, 23, and 26-30 displayed significant tumor cell growth inhibitory activity in vitro. The most active compound 27 exhibited ED50 values of 0.059-0.090 μM.