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4,5-Dimethoxycanthin-6-one

Names

[ CAS No. ]:
18110-87-7

[ Name ]:
4,5-Dimethoxycanthin-6-one

[Synonym ]:
Nigakinon-methylether
Methyl nigakinone
4,5-Dimethoxy-canthin-6-on
4,5-Dimethoxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one
6H-Indolo(3,2,1-de)(1,5)naphthyridin-6-one, 4,5-dimethoxy-
6H-Indolo[3,2,1-de][1,5]naphthyridin-6-one, 4,5-dimethoxy-
4,5-dimethoxy-6H-indolo[3,2,1-de]-1,5-naphthyridin-6-one
4,5-Dimethoxy-6-oxo-6H-indolo<3.2.1-de><1.5>naphthyridin

Biological Activity

[Description]:

4,5-Dimethoxycanthin-6-one is a potent and uncompetitive inhibitor of CYP1A2-mediated phenacetin O-deethylation with an IC50 value of 1.7μM and a Ki value of 2.6 μM. 4,5-Dimethoxycanthin-6-one, as an alkaloid, is isolated from the wood of Picrasma quassioides BENNET (Simaroubaceae)[1][2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450
Research Areas >> Metabolic Disease

[Target]

CYP1A2:1.7 μM (IC50)

CYP1A2:2.6 μM (Ki)


[In Vitro]

4,5-Dimethoxycanthin-6-one is a potent and uncompetitive inhibitor of CYP1A2-mediated phenacetin O-deethylation with an IC50 value of 1.7μM and a Ki value of 2.6 μM[2].

[References]

[1]. Taichi O, et al. Studies on the Constituents of Picrasma quassioides BENNET. III. The Alkaloidal Constituents

[2]. Miao X,et al. In vitro metabolism of 4, 5-dimethoxycanthin-6-one by human liver microsomes and its inhibition on human CYP1A2. Life Sci. 2017;190:46-51.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
455.1±45.0 °C at 760 mmHg

[ Melting Point ]:
145-146 °C

[ Molecular Formula ]:
C16H12N2O3

[ Molecular Weight ]:
280.278

[ Flash Point ]:
229.0±28.7 °C

[ Exact Mass ]:
280.084778

[ PSA ]:
52.83000

[ LogP ]:
2.16

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.688

Safety Information

[ Hazard Codes ]:
Xi

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds