189564-10-1

Basic information

• Product Name: (3S,4R,4aR,6S,6aS,12aR,12bS)-3,6-Dihydroxy-4-hydroxymethyl-4,6a,12b-trimethyl-9-phenyl-1,2,3,4,4a,5,6,6a,12a,12b-decahydro-7,10-dioxa-benzo[a]anthracene-11,12-dione
• Synonyms: (3S,4R,4aR,6S,6aS,12aR,12bS)-3,6-Dihydroxy-4-hydroxymethyl-4,6a,12b-trimethyl-9-phenyl-1,2,3,4,4a,5,6,6a,12a,12b-decahydro-7,10-dioxa-benzo[a]anthracene-11,12-dione
• CAS NO: 189564-10-1
• Molecular Weight: 454.52
• Mol File: 189564-10-1.mol

Chemical Properties

• CAS DataBase Reference: (3S,4R,4aR,6S,6aS,12aR,12bS)-3,6-Dihydroxy-4-hydroxymethyl-4,6a,12b-trimethyl-9-phenyl-1,2,3,4,4a,5,6,6a,12a,12b-decahydro-7,10-dioxa-benzo[a]anthracene-11,12-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R,4aR,6S,6aS,12aR,12bS)-3,6-Dihydroxy-4-hydroxymethyl-4,6a,12b-trimethyl-9-phenyl-1,2,3,4,4a,5,6,6a,12a,12b-decahydro-7,10-dioxa-benzo[a]anthracene-11,12-dione(189564-10-1)
• EPA Substance Registry System: (3S,4R,4aR,6S,6aS,12aR,12bS)-3,6-Dihydroxy-4-hydroxymethyl-4,6a,12b-trimethyl-9-phenyl-1,2,3,4,4a,5,6,6a,12a,12b-decahydro-7,10-dioxa-benzo[a]anthracene-11,12-dione(189564-10-1)

Safety Data

• Hazardous Substances Data: 189564-10-1(Hazardous Substances Data)

Upstream product

• 195527-11-8 (4aS,5S,6aR,7R,8S,10aS,10bR)-3-((Z)-2-Hydroxy-2-phenyl-vinyl)-4a,7,10a-trimethyl-1-oxo-5,8-bis-trimethylsilanyloxy-7-trimethylsilanyloxymethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester 
• 172704-62-0 (4aS,5S,6aR,7R,8S,10aS,10bR)-5,8-Dihydroxy-7-hydroxymethyl-3,4a,7,10a-tetramethyl-1-oxo-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester 
• 171925-86-3 Acetic acid (3S,4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-pyridin-3-yl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester 
• 189564-01-0 (4aS,5S,6aR,7R,8S,10aS,10bR)-3,4a,7,10a-Tetramethyl-1-oxo-5,8-bis-trimethylsilanyloxy-7-trimethylsilanyloxymethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester 
• 98-88-4 benzoyl chloride 
• 189564-06-5 (3S,4R,4aR,6S,6aS,12aR,12bS)-4,6a,12b-Trimethyl-9-phenyl-3,6-bis-trimethylsilanyloxy-4-trimethylsilanyloxymethyl-1,2,3,4,4a,5,6,6a,12a,12b-decahydro-7,10-dioxa-benzo[a]anthracene-11,12-dione 

Downstream Products

• 189564-14-5 Acetic acid (3S,4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-phenyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester 

Relevant articles and documents

New analogs of the pyripyropene family of ACAT inhibitors via α-pyrone fragmentation and γ-acylation/cyclization

The pyridine moiety of pyripyropene A was replaced with other aromatic and heteroaromatic substituents via α-pyrone degradation followed by dienolate γ-acylation and in situ cyclization.

Chemical modification and structure-activity relationships of pyripyropenes. 3. Synthetic conversion of pyridine-pyrone moiety

Structure-activity relationships of the pyridine-pyrone moiety in pyripyropene A (1), a potent acyl-CoA:cholesterol acyltransferase (ACAT) inhibitor of fungal origin, were studied. Several kinds of aromatic or hetero ring substituents for the pyridine moiety were synthesized using unique degradation reaction, following by γ-acylation. All the six synthesized analogs decreased the inhibitory activity with 20 to 200 times larger IC50 values than that of 1. Furthermore, the pyridine-pyrone substituent also dramatically decrease the inhibitory activity. Thus, the pyridine-pyrone moiety is important for eliciting potent ACAT inhibition.