162174-61-0

Basic information

• Product Name: 5,6-Dihydro-4-hydroxy-6-phenyl-6-propyl-2H-pyran-2-one
• Synonyms: 5,6-Dihydro-4-hydroxy-6-phenyl-6-propyl-2H-pyran-2-one
• CAS NO: 162174-61-0
• Molecular Weight: 232.279
• Mol File: 162174-61-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 5,6-Dihydro-4-hydroxy-6-phenyl-6-propyl-2H-pyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Dihydro-4-hydroxy-6-phenyl-6-propyl-2H-pyran-2-one(162174-61-0)
• EPA Substance Registry System: 5,6-Dihydro-4-hydroxy-6-phenyl-6-propyl-2H-pyran-2-one(162174-61-0)

Safety Data

• Hazardous Substances Data: 162174-61-0(Hazardous Substances Data)

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 495-40-9 propiophenone 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 162174-68-7 5,6-dihydro-4-hydroxy-6-phenyl-6-propyl-3-(1-phenyl-2E-propenyl)-2H-pyran-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 

Relevant articles and documents

Synthesis and antitumor activity of 4-hydroxycoumarin derivatives

A series of 4-hydroxycoumarin derivatives was prepared and evaluated for antitumor activity against five human tumor cell lines. A series of 4-hydroxycoumarin derivatives was prepared and evaluated for antitumor activity. The key fragments were 2a-c, 5c, 12b, 13b, 17, and 18 which were prepared via dianion ring cyclization, Friedel-Crafts acylation, and Reformatsky reaction. Compound 20b showed the most potent antitumor activity among the total 12 derivatives and compounds 19a and 19b exhibited efficacy comparable to etoposide in vitro antitumor activity.

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.