71601-13-3

Upstream product

• 74-88-4 methyl iodide 
• 711-79-5 1-hydroxy-2-acetonaphthone 
• 591-31-1 3-methoxy-benzaldehyde 
• 586-38-9 3-Methoxybenzoic acid 
• 71601-11-1 2-acetylnaphthalen-1-yl 3-methoxybenzoate 
• 71601-12-2 1-(1-Hydroxy-2-naphthalinyl)-3-(3-methoxyphenyl)-1,3-propandion 
• 57822-43-2 C₂₀H₁₆O₃ 

Relevant academic research and scientific papers

Synthesis and structure-activity relationship studies of α-naphthoflavone derivatives as CYP1B1 inhibitors

Cytochrome P450 1B1(CYP1B1) has been recognized as an important target for cancer prevention and drug resistance reversal. In order to obtain potent and selective CYP1B1 inhibitors, a series of forty-one α-naphthoflavone (ANF) derivatives were synthesized, characterized, and evaluated for CYP1B1, CYP1A1 and CYP1A2 inhibitory activities. A closure look into the structure-activity relationship for the inhibitory effects on CYP1B1 indicated that modification of the C ring of ANF would decrease the CYP1B1 inhibitory potency, while incorporation of substituent(s) into the different positions of the B ring yielded analogues with varying CYP1B1 inhibitory capacity. Among these derivatives, compounds 9e and 9j were identified as the most potent two selective CYP1B1 inhibitors with IC50 values of 0.49 and 0.52 nM, respectively, which were 10-fold more potent than the lead compound ANF. In addition, molecular docking and a reasonable 3D-QSAR (three-dimensional quantitative structure-activity relationship) study were performed to provide a better understanding of the key structural features influencing the CYP1B1 inhibitory activity. The results achieved in this study would lay a foundation for future development of selective, potent, low-toxic and water-soluble CYP1B1 inhibitors.

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.

Fungal metabolism of naphthoflavones

Naphthoflavones (benzoflavones) are synthetic flavonoids commonly used in drug metabolism studies as selective activators or inhibitors of cytochrome P-450 enzymes. Nowadays they are also used as a component of food supplements for body builders. There is

Synthesis of methoxybenzoflavones and assignments of their NMR data

A phytotoxic root exudate from Acroptilon repens was identified as 7,8-benzoflavone, an inhibitor of cytochrome P450 1A2 and activator of cytochrome P450 3A4. The synthetic 5,6-benzoflavone also is a potent phytotoxin. Six 7,8-benzoflavones and eight 5,6-benzoflavones were synthesized in this study. The NMR data for a few of these compounds have been previously reported; however, the NMR data for most of them have not been reported. For reference purposes, the complete NMR data for the 14 benzoflavones are described.