119930-36-8

Upstream product

• 41309-43-7 (2-bromovinyl)trimethylsilane 
• 100-52-7 benzaldehyde 
• 41309-43-7 (2-bromovinyl)trimethylsilane 
• 79-22-1 methyl chloroformate 

Downstream Products

• 119930-35-7 2-((E)-1-Phenyl-3-trimethylsilanyl-allyl)-malonic acid dimethyl ester 
• 40595-34-4 (E)-trimethyl(3-phenylallyl)silane 
• 119930-34-6 (E)-2-Acetyl-3-phenyl-5-trimethylsilanyl-pent-4-enoic acid methyl ester 
• 119793-72-5 (E)-2-(3-phenyl-allyl) malonic acid dimethyl ester 
• 162174-69-8 4-hydroxy-1-oxa-8-(1-phenyl-3-trimethylsilyl-2E-propenyl)spiro[5.5]undec-3-en-2-one 
• 162174-67-6 5,6-Dihydro-4-hydroxy-6-phenyl-6-propyl-3-(1-phenyl-3-trimethylsilyl-2E-propenyl)-2H-pyran-2-one 
• 183963-64-6 12-Hydroxy-11-((E)-1-phenyl-3-trimethylsilanyl-allyl)-1,4,9-trioxa-dispiro[4.2.5.2]pentadec-11-en-10-one 
• 162168-58-3 5,6-Dihydro-4-hydroxy-6-phenyl-6-(phenylmethyl)-3-(1-phenyl-2-propenyl)-2H-pyran-2-one 
• 162168-64-1 5,6-Dihydro-4-hydroxy-6-(2-phenylethyl)-3-(1-phenyl-2-propenyl)-6-propyl-2H-pyran-2-one 
• 162168-49-2 12-Hydroxy-11-(1-phenyl-propyl)-1,4,9-trioxa-dispiro[4.2.5.2]pentadec-11-en-10-one 

Relevant academic research and scientific papers

Pyran-2-ones and 5,6-dihydropyran-2-ones useful for treating hyperplasia and other diseases

Certain 2H-pyran-2-ones are useful for treating benign prostatic hypertrophy or hyperplasia, prostatic cancer, alopecia, hirsutism, acne vulgaris and seborrhea.

Structure-based design of HIV protease inhibitors: 5,6-dihydro-4- hydroxy-2-pyrones as effective, nonpeptidic inhibitors

From a broad screening program, the 4-hydroxycoumarin phenprocoumon (I) was previously identified as a lead template with HIV protease inhibitory activity. The crystal structure of phenprocoumon/HIV protease complex initiated a structure-based design effort that initially identified the 4- hydroxy-2-pyrone U-96988 (II) as a first-generation clinical candidate for the potential treatment of HIV infection. Based upon the crystal structure of the 4-hydroxy-2-pyrone III/HIV protease complex, a series of analogues incorporating a 5,6-dihydro-4-hydroxy-2-pyrone template were studied. It was recognized that in addition to having the required pharmacophore (the 4- hydroxy group with hydrogen-bonding interaction with the two catalytic aspartic acid residues and the lactone moiety replacing the ubiquitous water molecule in the active site), these 5,6-dihydro-4-hydroxy-2-pyrones incorporated side chains at the C-6 position that appropriately extended into the S1' and S2' subsites of the enzyme active site. The crystal structures of a number of representative 5,6-dihydro-4-hydroxy-2-pyrones complexed with the HIV protease were also determined to provide better understanding of the interaction between the enzyme and these inhibitors to aid the structure- based drug design effort. The crystal structures of the ligands in the enzyme active site did not always agree with the conformations expected from experience with previous pyrone inhibitors. This is likely due to the increased flexibility of the dihydropyrone ring. From this study, compound XIX exhibited reasonably high enzyme inhibitory activity (K(i) = 15 nM) and showed antiviral activity (IC50 = 5 μM) in the cell-culture assay. This result provided a research direction which led to the discovery of active 5,6-dihydro-4-hydroxy-2-pyrones as potential agents for the treatment of HIV infection.