425646-73-7

Basic information

• Product Name: 5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-2-phenyl-1,3-dioxane-4,6-dione
• Synonyms: 5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-2-phenyl-1,3-dioxane-4,6-dione
• CAS NO: 425646-73-7
• Molecular Formula: C18H13BrO6
• Molecular Weight: 405.19622
• Mol File: 425646-73-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-2-phenyl-1,3-dioxane-4,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-2-phenyl-1,3-dioxane-4,6-dione(425646-73-7)
• EPA Substance Registry System: 5-(3-bromo-4-hydroxy-5-methoxybenzylidene)-2-phenyl-1,3-dioxane-4,6-dione(425646-73-7)

Safety Data

• Hazardous Substances Data: 425646-73-7(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 3709-16-8 2-phenyl-1,3-dioxane-4,6-dione 
• 2973-76-4 5-bromo-4-hydroxy-3-methoxybenzaldehyde 

Relevant articles and documents

Discovery of 5-Benzylidene-2-phenyl-1,3-dioxane-4,6-diones as Highly Potent and Selective SIRT1 Inhibitors

SIRT1, a member of the sirtuin family, catalyzes the deacetylation of proteins with the transformation of NAD+ into nicotinamide and 2′-O-acetyl-ADP-ribose. Selective SIRT1/2 inhibitors have potential application in the chemotherapy of colorectal carcinoma, prostate cancer, and myelogenous leukemia. Here we identified novel SIRT1 inhibitors with the scaffold of 5-benzylidene-2-phenyl-1,3-dioxane-4,6-dione. The most potent inhibitor 12n displayed an IC50 of 460 nM and a selectivity for SIRT1 over SIRT2, SIRT3, and SIRT5 of 113.5-, 254.3-, and 10.83-fold, respectively. It did not affect the activity of SIRT6. To elucidate the inhibitory mechanism, we determined the inhibition type of the inhibitor by enzyme kinetic analysis, showing that the inhibitor was competitive to the acetyl peptide and noncompetitive to NAD+. Further, the interaction of the inhibitor in SIRT1 was studied by using molecular docking, which was validated by the structure-activity relationship analysis of the inhibitors and the site-directed mutagenesis of SIRT1. Consistent with the in vitro assays, the inhibitors increased the acetylation level of p53 in a concentration-dependent manner in cells.

1,3-dioxane-4,6-dione compound, preparation method, medicine composition and application thereof

The invention discloses a 1,3-dioxane-4,6-dione compound, a preparation method, a medicine composition and application thereof. The structure of the compound is as shown in a formula I, and the definition of each substituent is as shown in the description