62502-14-1

Basic information

• Product Name: 3-(1,3-benzodioxol-5-yl)-8,8-dimethyl-4H,8H-pyrano[2,3-f]chromen-4-one
• Synonyms: 3-(1,3-Benzodioxol-5-yl)-8,8-dimethyl-4H,8H-pyrano[2,3-f]chromen-4-one
• CAS NO: 62502-14-1
• Molecular Formula: C₂₁H₁₆O₅
• Molecular Weight: 348.3487
• Mol File: 62502-14-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 531.8°C at 760 mmHg
• Flash Point: 235.5°C
• Density: 1.339g/cm³
• Vapor Pressure: 2.17E-11mmHg at 25°C
• Refractive Index: 1.634
• CAS DataBase Reference: 3-(1,3-benzodioxol-5-yl)-8,8-dimethyl-4H,8H-pyrano[2,3-f]chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1,3-benzodioxol-5-yl)-8,8-dimethyl-4H,8H-pyrano[2,3-f]chromen-4-one(62502-14-1)
• EPA Substance Registry System: 3-(1,3-benzodioxol-5-yl)-8,8-dimethyl-4H,8H-pyrano[2,3-f]chromen-4-one(62502-14-1)

Safety Data

• Hazardous Substances Data: 62502-14-1(Hazardous Substances Data)

Upstream product

• 2861-28-1 1,3-benzodioxole-5-acetic acid 
• 6845-81-4 3,4-methylenedioxyphenylacetyl chloride 
• 1740-74-5 1,1-diethoxy-3-methyl-2-butene 
• 90-29-9 7-hydroxy-3',4'-methylenedioxyisoflavone 
• 108-46-3 recorcinol 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 935659-63-5 3-iodo-7-((tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one 
• 1124174-55-5 C₁₆H₂₁NO₄ 
• 111841-07-7 2-hydroxy-4-(tetrahydropyran-2-yloxy)acetophenone 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 1422513-84-5 3-iodo-8,8-dimethylpyrano[2,3-f]chromen-4(8H)-one 
• 94839-07-3 3,4-(methylenedioxy)-benzeneboronic acid 
• 1013634-99-5 7-hydroxy-3-iodo-4H-chromen-4-one 
• 35453-09-9 2-(3,4-methylenedioxyphenyl)-1-(methylsulfinyl)-1-(methylthio)ethylene 

Relevant articles and documents

Highly selective carbamate-based butyrylcholinesterase inhibitors derived from a naturally occurring pyranoisoflavone

This current study described the design and synthesis of a series of derivatives based on a natural pyranoisaflavone, which was obtained from the seeds of Millettia pachycarpa and displayed attractive BChE inhibition and high selectivity in our previous study. The inhibitory potential of all derivatives against two cholinesterases was evaluated. Only a few compounds demonstrated AChE inhibitory activity at the tested concentrations, while 26 compounds showed significant inhibition on BChE (the IC50 values varied from 9.34 μM to 0.093 μM), most of them presented promising selectivity to ward BChE. Prediction of ADME properties for 7 most active compounds was performed. Among them, 9g (IC50 = 222 nM) and 9h (IC50 = 93 nM) were found to be the most potent BChE inhibitors with excellent selectivity over AChE (SI ratio = 1339 and 836, respectively). The kinetic analysis demonstrated both of them acted as mixed-type BChE inhibitors, while the molecular docking results indicated that they interacted with both residues in the catalytic active site. A cytotoxicity test on PC12 cells showed that both 9g and 9h had a therapeutic safety range similar to tacrine. Overall, the results indicate that 9h could be a good candidate of BChE inhibitors.

Synthesis, structure-activity relationships and biological evaluation of barbigerone analogues as anti-proliferative and anti-angiogenesis agents

A series of barbigerone analogues (7a-7w, 13a-13x) were designed, synthesized and biologically evaluated for their anti-proliferative and anti-angiogenic activities. Among these compounds, compound 13a exhibited the most potent inhibitory effect on the proliferation of HUVECs, HepG2, A375, U251, B16, and HCT116 cells (IC50 = 3.80, 0.28, 1.58, 3.50, 1.09 and 0.68 μM, respectively). Compound 13a inhibited the angiogenesis in zebrafish embryo assay in a concentration-dependent manner. Furthermore, 13a also effectively inhibited the migration and capillary like tube formation of human umbilical vein endothelial cell in vitro. These results support the further investigation of this class of compounds as potential anti-proliferative and anti-angiogenesis agents.