652138-31-3

Basic information

• Product Name: 4H-Naphtho[1,2-b]pyran-4-one, 6-bromo-2-(2-fluorophenyl)-
• CAS NO: 652138-31-3
• Molecular Formula: C19H10BrFO2
• Molecular Weight: 369.19
• Mol File: 652138-31-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4H-Naphtho[1,2-b]pyran-4-one, 6-bromo-2-(2-fluorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-Naphtho[1,2-b]pyran-4-one, 6-bromo-2-(2-fluorophenyl)-(652138-31-3)
• EPA Substance Registry System: 4H-Naphtho[1,2-b]pyran-4-one, 6-bromo-2-(2-fluorophenyl)-(652138-31-3)

Safety Data

• Hazardous Substances Data: 652138-31-3(Hazardous Substances Data)

Usage

Chemical compound

4H-Naphtho[1,2-b]pyran-4-one, 6-bromo-2-(2-fluorophenyl)-

Structure

Naphthopyran structure containing a bromine atom and a fluorophenyl group

Molecular weight

341.171 g/mol
Potential pharmaceutical or industrial applications
Unique structure and properties
Specific uses and effects depend on interactions with other chemicals and biological systems
Further research needed to fully understand potential uses

Upstream product

• 52220-64-1 1-(4-bromo-1-hydroxynaphthalen-2-yl)ethanone 

Relevant articles and documents

Benzoflavone activators of the cystic fibrosis transmembrane conductance regulator: Towards a pharmacophore model for the nucleotide-binding domain

Our previous screen of flavones and related heterocycles for the ability to activate the cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel indicated that UCCF-029, a 7,8-benzoflavone, was a potent activator. In the present study, we describe the synthesis and evaluation, using cell-based assays, of a series of benzoflavone analogues to examine structure-activity relationships and to identify compounds having greater potency for activation of both wild type CFTR and a mutant CFTR (G551D-CFTR) that causes cystic fibrosis in some human subjects. Using UCCF-029 as a structural guide, a panel of 77 flavonoid analogues was prepared. Analysis of the panel in FRT cells indicated that benzannulation of the flavone A-ring at the 7,8-position greatly improved compound activity and potency for several flavonoids. Incorporation of a B-ring pyridyl nitrogen either at the 3- or 4-position also elevated CFTR activity, but the influence of this structural modification was not as uniform as the influence of benzannulation. The most potent new analogue, UCCF-339, activated wild-type CFTR with a Kd of 1.7 μM, which is more active than the previous most potent flavonoid activator of CFTR, apigenin. Several compounds in the benzoflavone panel also activated G551D-CFTR, but none were as active as apigenin. Pharmacophore modeling suggests a common binding mode for the flavones and other known CFTR activators at one of the nucleotide-binding sites, allowing for the rational development of more potent flavone analogues.