1165-94-2

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 8-iodo-5,7-dimethoxy-2-(4-methoxyphenyl)-
• CAS NO: 1165-94-2
• Molecular Formula: C18H15IO5
• Molecular Weight: 438.219
• Mol File: 1165-94-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 8-iodo-5,7-dimethoxy-2-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 8-iodo-5,7-dimethoxy-2-(4-methoxyphenyl)-(1165-94-2)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 8-iodo-5,7-dimethoxy-2-(4-methoxyphenyl)-(1165-94-2)

Safety Data

• Hazardous Substances Data: 1165-94-2(Hazardous Substances Data)

Upstream product

• 5631-70-9 4',5,7-trimethoxyflavone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 3420-72-2 2'-hydroxy-4,4',6'-trimethoxychalcone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 1734-84-5 (E)-1-(2-hydroxy-3-iodo-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 

Downstream Products

• 5631-70-9 4',5,7-trimethoxyflavone 
• 107225-53-6 8-[5-(5,7-dimethoxy-4-hydroxyimino-4H-chromen-2-yl)-2-methoxy-phenyl]-5,7-dimethoxy-2-(4-methoxy-phenyl)-chromen-4-one oxime 
• 13738-92-6 cupressuflavone 4',4',7,7-tetramethyl ether 
• 674367-91-0 5,7-Dimethoxy-2-(4-methoxy-phenyl)-8-((E)-3-methyl-buta-1,3-dienyl)-chromen-4-one 
• 2222-38-0 I-4',II-4',I-5,II-5,I-7,II-7-hexa-O-methylcupressuflavone 
• 61110-43-8 6-C-methylhexa-O-methylamentoflavone 
• 3778-26-5 Amentoflavon 

Relevant articles and documents

Discovery of Novel Apigenin-Piperazine Hybrids as Potent and Selective Poly (ADP-Ribose) Polymerase-1 (PARP-1) Inhibitors for the Treatment of Cancer

Poly (ADP-ribose) polymerase-1 (PARP-1) is a potential target for the discovery of chemosensitizers and anticancer drugs. Amentoflavone (AMF) is reported to be a selective PARP-1 inhibitor. Here, structural modifications and trimming of AMF have led to a series of AMF derivatives (9a-h) and apigenin-piperazine/piperidine hybrids (14a-p, 15a-p, 17a-h, and 19a-f), respectively. Among these compounds, 15l exhibited a potent PARP-1 inhibitory effect (IC50 = 14.7 nM) and possessed high selectivity to PARP-1 over PARP-2 (61.2-fold). Molecular dynamics simulation and the cellular thermal shift assay revealed that 15l directly bound to the PARP-1 structure. In in vitro and in vivo studies, 15l showed a potent chemotherapy sensitizing effect against A549 cells and a selective cytotoxic effect toward SK-OV-3 cells through PARP-1 inhibition. 15l·2HCl also displayed good ADME characteristics, pharmacokinetic parameters, and a desirable safety margin. These findings demonstrated that 15l·2HCl may serve as a lead compound for chemosensitizers and the (BRCA-1)-deficient cancer therapy.

Synthesis, resolution, and absolute configuration of optically pure 5,5''-dihydroxy-4',4''',7,7''-tetramethoxy-8,8''-biflavone and its derivatives

Optically pure 5,5-dihydroxy-4,4''',7,7''-tetramethoxy-8,8''-biflavone (1) and its dimethyl derivative 5 were synthesized for the first time. Resolution of the racemic (±)-1, prepared by a modified literature procedure, was performed via the formation and recrystallization of its (+)- and (-)-camphorsulfonate 6. Hydrolysis of the (+)- or (-)-camphorsulfonate 6 afforded optically pure (+) or (-)-1, which was then methylated to give (+)- or (-)-5. The absolute configurations of (+)-1 and (-)-1, assigned as (aR) and (aS), respectively, were confirmed in an unambiguous manner by X-ray single crystal analysis and from their CD spectra.