190385-15-0

Basic information

• Product Name: endo rocaglic acid
• Synonyms: endo rocaglic acid
• CAS NO: 190385-15-0
• Molecular Weight: 478.499
• Mol File: 190385-15-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: endo rocaglic acid(CAS DataBase Reference)
• NIST Chemistry Reference: endo rocaglic acid(190385-15-0)
• EPA Substance Registry System: endo rocaglic acid(190385-15-0)

Safety Data

• Hazardous Substances Data: 190385-15-0(Hazardous Substances Data)

Upstream product

• 143901-35-3 aglafoline 
• 901774-46-7 keto rocaglate 
• 1160457-37-3 1-[4,6-dimethoxy-2-(4-methoxyphenyl)benzofuran-3-yl]-3-phenylprop-2-yn-1-ol 
• 1160457-39-5 3-(1-(4-methoxybenzyloxy)-3-phenylprop-2-ynyl)-4,6-dimethoxy-2-(4-methoxyphenyl)benzofuran 
• 1160457-28-2 4,6-dimethoxy-2-(4-methoxyphenyl)-3-vinylbenzofuran 
• 95125-08-9 4,6-dimethoxy-2-(4-methoxyphenyl)benzofuran-3-carboxaldehyde 
• 108-73-6 3,5-dihydroxyphenol 
• 33646-40-1 4-methoxymandelonitrile 
• 117828-32-7 4,6-dihydroxy-2-(4-methoxyphenyl)benzofuran-3(2H)-one 
• 132464-02-9 (3aS,8bR)-methyl 8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-3a,8b-dihydro-1H-cyclopenta[b]-benzofuran-2-carboxylate 
• 132464-01-8 (3aS,8bR)-methyl 6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-8b-((trimethylsilyl)oxy)-3a,8b-dihydro-1H-cyclopenta[b]-benzofuran-2-carboxylate 
• 132464-00-7 (2R,3S,3aR,8bR)-methyl 6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-8b-((trimethylsilyl)oxy)-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxylate 
• 117828-33-8 4,6-dimethoxy-2-(4-methoxyphenyl)benzofuran-3(2H)-one 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 84573-16-0 rocaglamide 
• 1352914-52-3 (?)-CR-1-31-B 
• 1554275-14-7 (-)-(2aR,3S,3aR,8bS,8cR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-3,3a,8b,8c-tetrahydro-oxeto[2',3':3,4]cyclopenta[1,2-b]benzofuran-2(2aH)-one 

Relevant articles and documents

Synthesis of rocaglamide hydroxamates and related compounds as eukaryotic translation inhibitors: Synthetic and biological studies

The rocaglates/rocaglamides are a class of natural products known to display potent anticancer activity. One such derivative, silvestrol, has shown activity comparable to taxol in certain settings. Here, we report the synthesis of various rocaglamide anal

Remodeling natural products: Chemistry and serine hydrolase activity of a rocaglate-derived β-lactone

Flavaglines are a class of natural products with potent insecticidal and anticancer activities. β-Lactones are a privileged structural motif found in both therapeutic agents and chemical probes. Herein, we report the synthesis, unexpected light-driven di-epimerization, and activity-based protein profiling of a novel rocaglate-derived β-lactone. In addition to in vitro inhibition of the serine hydrolases ABHD10 and ACOT1/2, the most potent β-lactone enantiomer was also found to inhibit these enzymes, as well as the serine peptidases CTSA and SCPEP1, in PC3 cells.

ASYMMETRIC SYNTHESIS OF ROCAGLAMIDES VIA ENANTIOSELECTIVE PHOTOCYCLOADDITION MEDIATED BY CHIRAL BRONSTED ACIDS

The present invention provides a new strategies for the synthesis of compounds of the rocaglamide family and related natural products. The synthetic approach generally involves photochemical generation of an oxidopyrylium species from a 3-hydroxychromone derivative followed by an enantioselective 1,3-dipolar cycloaddition of the oxidopyrylium species to a dipolarophile in the presence of a TADDOL derivative. This approach can be used for the formation of adducts containing an aglain core structure. Methods of the conversion of aglain core structures to aglain, rocaglamide and forbaglin ring systems are also provided. The present invention also relates to the use of rocaglamide/aglain/forbaglin derivatives for the manufacture of medicaments for use in the treatment of cancer or cancerous conditions, disorders associated with cellular hyperproliferation, or NF-κB-dependent conditions.