32265-03-5

Upstream product

• 140-29-4 phenylacetonitrile 
• 1663-67-8 malonoyl dichloride 

Downstream Products

• 139588-85-5 6-chloro-4-hydroxy-1-methyl-5-phenyl-2(1H)-pyridone 
• 102249-52-5 4-hydroxy-5-phenylpyridin-2(1H)-one 
• 181712-71-0 6-Chloro-4-hydroxy-3-nitro-5-phenyl-1H-pyridin-2-one 
• 920744-20-3 6-chloro-4-hydroxy-2-oxo-5-phenyl-1,2-dihydropyridine-3-carbaldehyde 
• 1353390-19-8 (1'R,2'R)-2,4-bis(benzyloxy)-6-chloro-3-(2-methyl-1-prop-2-ynyloxybut-3-enyl)-5-phenylpyridine 
• 1353390-18-7 (2S,3R)-3-(2,4-bis(benzyloxy)-6-chloro-5-phenylpyridin-3-yl)-3-hydroxy-2-methylpropanal 
• 1353390-17-6 (1R,2R)-1-(2,4-bis(benzyloxy)-6-chloro-5-phenylpyridin-3-yl)-2-methylbut-3-en-1-ol 
• 139588-99-1 3-deuterio-4-methoxy-1-methyl-5-phenyl-2(1H)-pyridone 
• 139588-88-8 2-chloro-6-methoxy-1-methyl-5-phenyl-2(1H)-pyridone 
• 139588-86-6 6-chloro-4-methoxy-1-methyl-5-phenyl-2(1H)-pyridone 
• 139588-87-7 4-methoxy-1-methyl-5-phenyl-2(1H)-pyridone 

Relevant academic research and scientific papers

New strategy for the synthesis of phosphatase inhibitors TMC-69-6H and analogs

An efficient method for the synthesis of antitumor TMC-69-6H and related analogs which have been demonstrated to be phosphatase (PTP1B, VHR, and PP1) inhibitors, is reported. This strategy involves two key steps: a diastereoselective aldol reaction and a

Synthesis and antifungal activity of polycyclic pyridone derivatives with anti-hyphal and biofilm formation activity against Candida albicans

Thirty-five pyridone derivatives were synthesized, with derivatization conducted on polycyclic pyridone scaffolds, including cis- or trans-oxydecalin and other cyclic structures, by domino-Knoevenagel-electrocyclic reactions. The anti-fungal activities of the synthesized compounds were tested against Candida albicans. Ten compounds inhibited hyphal formation without inhibiting growth. Pyridones with anti-hyphal formation activity (4c, 6d, 12a and 12c) were tested for their ability to inhibit biofilm formation. Compound 6d showed both anti-hyphal and biofilm inhibition activity.

Formal synthesis of TMC-69-6H via a one-pot enantioselective domino proline-mediated aldol/olefin homologation procedure

Enantioselective synthesis of TMC-69-6H was accomplished from readily accessible pyridone derivative via a domino proline-mediated aldol reaction/olefin homologation, followed by tandem ring-closing and cross metathesis.

PYRIDONE GPR119 G PROTEIN-COUPLED RECEPTOR AGONISTS

Novel compounds are provided which are GPR119 G protein-coupled receptor modulators. GPR119 G protein-coupled receptor modulators are useful in treating, preventing, or slowing the progression of diseases requiring GPR 119 G protein-coupled receptor modulator therapy. These novel compounds have the structure Formula I or Formula IA.

Synthesis and evaluation of the antitumor agent TMC-69-6H and a focused library of analogs

A concise, efficient and flexible total synthesis of the potent antitumor agent TMC-69-6H (2) is described. Key steps involve the palladium catalyzed regioselective addition of 4-hydroxy-2-pyridone 5 to pyranyl acetate 6 which is accompanied by a spontaneous 1,4-addition of the phenolic -OH group to the emerging enone to give the tricyclic product 7 in excellent yield. When this reaction is carried out with optically enriched (S)-6 (conveniently prepared by a lipase catalyzed kinetic dynamic resolution) in the presence of the chiral ligand (S,S)-12 and allylpalladium chloride dimer, the ensuing matched situation delivers the key building block (-)-7 in 96% ee. Its further elaboration into 2 involves a Julia-Kocienski olefination with tetrazolylsulfone 19 and a final N-oxidation effected by the peroxomolybdenum complex [(pyridine)MoO 5(HMPA)] to form the hydroxamic acid motif. The flexibility inherent to this route allows for the preparation of a focused library of analogues for biochemical evaluation. The results obtained show that N-hydroxy-2-pyridone derivatives constitute a promising new class of selective phosphatase inhibitors. In contrast to previous reports in the literature, however, TMC-69-6H and congeners are found to exhibit pronounced activities against the tyrosine protein phosphatase PTB1B, the dual specific phosphatase VHR, and the serine/threonine phosphatase PP1, while being only weak inhibitors for the dual specific phosphatases Cdc25 A and B. Two key intermediates of the synthesis route have been characterized by X-ray crystallography. Graphical Abstract.

Total synthesis of (±)-leporin A

An efficient synthesis of (±)-leporin A (1) has been developed using a tandem Knoevenagel condensation-inverse electron demand intramolecular hetero Diels-Alder reaction to construct the key tricyclic intermediate 3 from pyridone 5 and dienal 6 in one pot in 35% yield. Hydroxylation (71%) of 3 and methylation (77%) of the resulting hydroxypyridone 2 completed the first total synthesis of (±)-leporin A (1).

Lithiation of 4-Methoxy-2-pyridones. Synthetic Entry to Tenellin and Funiculosin, and Related Natural 3,5-Disubstituted 4-Oxy-2-pyridones

Lithiation of 4-methoxy-2-pyridone with butyllithium at -78 deg C occurs at the C-3 position exclusively.Subsequent reactions with MeOD, MeI, CO2, benzaldehyde or (E)-but-2-enal then lead to the corresponding C-3-substituted derivatives. in a one-pot procedure, treatment of 1,2-dihydro-4-methoxy-1-methyl-2-oxopyridine-3-carboxylic acid with ammonia in the presence of a polyphosphate buffer at 80 deg C produced natural ricinine in 58percent overall yield.A convenient three-step synthesis of 5-aryl- and 5-alkyl-substituted 4-methoxy-2-pyridones is described.Lithiation of these substrates, followed by reaction with electrophiles, provided a convenient route to 3,5-disubstituted 4-oxy-2-pyridones, and a synthetic entry to natural products, e. g. tenellin and funiculosin, containing this structural feature.