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• 604-59-1 α-naphtoflavone 

Relevant academic research and scientific papers

Hg2+-selective fluorogenic chemodosimeter based on naphthoflavone

A new Hg2+-selective chemodosimeter based on α-naphthoflavone was investigated. The chemodosimetric behavior is based on the Hg2+-triggered desulfurization of flavothione into its oxygen analogue flavone. The signaling was effective in aqueous environment and the selective signaling was not affected in the presence of common physiologically and environmentally important metal ions.

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.

ORGANOPHOSPHORUS COMPOUNDS ACTION OF 2,4-BIS-(4-METHOXYPHENYL)-1,3,2,4-DITHIADIPHOSPHETANE-2,4-DISULFIDE (LAWESSON REAGENT) AND 2,4-BIS-(PHENYLTHIO)-1,3-DITHIA-2,4-DIPHOSPHETANE-2,4-DISULFIDE (JAPANESE REAGENT) ON FLAVONE, α-NAPHTHOFLAVONE AND β-NAPHTHOFLAVONE

Japanese reagent JR, 1b converts 2-phenyl-(5,6-benz)-γ-pyrone (flavone, 2a) into 2-phenyl-5,6-benzpyrane-4-thione 2b.Lawesson reagent LR, 1a converts 2-phenyl-7,8-benzo-1,4-chromone (α-naphthoflavone, 3a) and 2-phenyl-5,6-benzo-1,4-chromone (β-naphthoflavone 4a) into their corresponding thioketones 3b and 4b respectively.Thiation of 3a and 4a with Lawesson reagent, 1a can be induced photochemically to give 3b and 4b.Thiation of α-naphthoflavone 3a and β-naphthoflavone 4a with Japanese reagent JR, 1b is accompanied with ring opening at the heterocyclic oxygen atom of the γ-pyrone ring, to yield products 5 and 6 respectively.The given structures were based upon analytical, chemical and spectroscopic results. Key words: Lawesson reagent; Japanese reagent; thiation; γ-pyrones.