98166-67-7

Basic information

• Product Name: 4H-Naphtho[1,2-b]pyran-4-one, 2-(4-hydroxyphenyl)-
• Synonyms: 2-(4-hydroxy-phenyl)-benzo[h]chromen-4-one;HMS3044P09;4H-Naphtho[1,2-b]pyran-4-one,2-(4-hydroxyphenyl);2-(4-Hydroxy-phenyl)-benzo[h]chromen-4-on
• CAS NO: 98166-67-7
• Molecular Formula: C19H12O3
• Molecular Weight: 288.302
• Mol File: 98166-67-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4H-Naphtho[1,2-b]pyran-4-one, 2-(4-hydroxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-Naphtho[1,2-b]pyran-4-one, 2-(4-hydroxyphenyl)-(98166-67-7)
• EPA Substance Registry System: 4H-Naphtho[1,2-b]pyran-4-one, 2-(4-hydroxyphenyl)-(98166-67-7)

Safety Data

• Hazardous Substances Data: 98166-67-7(Hazardous Substances Data)

Upstream product

• 370583-68-9 1-(1-hydroxy-[2]naphthyl)-3-(4-methoxy-phenyl)-propane-1,3-dione 
• 934163-66-3 2-acetylnaphthalen-1-yl 4-methoxybenzoate 
• 100-09-4 4-methoxybenzoic acid 
• 604-59-1 α-naphtoflavone 
• 40649-75-0 2'-Hydroxy-4-methoxy-3',4'-benzochalkone 
• 123-11-5 4-methoxy-benzaldehyde 
• 711-79-5 1-hydroxy-2-acetonaphthone 
• 14756-22-0 UCCF 269 

Relevant articles and documents

Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone

Selective cytochrome P450 (CYP) 1B1 inhibition has potential as an anticancer strategy that is unrepresented in the current clinical arena. For development of a selective inhibitor, we focused on the complexity caused by sp3-hybridized carbons and synthesized a series of benzo[h]chromone derivatives linked to a non-aromatic B-ring using α-naphthoflavone (ANF) as the lead compound. Ring structure comparison suggested compound 37 as a suitable cyclohexyl-core with improved solubility. Structural evolution of 37 produced the azide-containing cis-49a, which had good properties in three important respects: (1) selectivity for CYP1B1 over CYP1A1 and CYP1A2 (120-times and 150-times, respectively), (2) greater inhibitory potency of >2 times that of ANF, and (3) improved solubility. The corresponding aromatic B-ring compound 59a showed low selectivity and poor solubility. To elucidate the binding mode, we performed X-ray crystal structure analysis, which revealed the interaction mode and explained the subtype selectivity of cis-49a.

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.