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282219

Sigma-Aldrich

Benz[g]isoquinoline-5,10-dione

99%

Synonym(s):

2-Aza-9,10-anthraquinone

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About This Item

Empirical Formula (Hill Notation):
C13H7NO2
CAS Number:
46492-08-4
Molecular Weight:
209.20
MDL number:
MFCD00010399
UNSPSC Code:
12352100
PubChem Substance ID:
24857029
NACRES:
NA.22

Assay

99%

mp

178-180 °C (lit.)

functional group

ketone

SMILES string

O=C1c2ccccc2C(=O)c3cnccc13

InChI

1S/C13H7NO2/c15-12-8-3-1-2-4-9(8)13(16)11-7-14-6-5-10(11)12/h1-7H

InChI key

ZLLVUAAESHIVAZ-UHFFFAOYSA-N

General description

Benz[g]isoquinoline-5,10-dione has been isolated as an active component from the ethanolic extract of the aerial parts of Mitracarpus scaber. It exhibits significant in vitro inhibitory activity against the AIDS-related pathogens. The in vitro antibacterial and anti-fungal activity of benz[g]isoquinoline-5,10-dione has been investigated using the agar well-diffusion assay.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
01328DW

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A M Clark et al.
Pharmaceutical research, 1(6), 269-271 (1984-11-01)
The in vitro antibacterial and anti-fungal activity of benz[g]isoquinoline-5,10-dione (1), benzo[g]quinoline-5, 10-dione (2), benzo[g]quinoline-5,6-dione (3), and anthraquinone (4) was determined using the agar well-diffusion assay. The minimum inhibitory concentrations (MIC's) of each of the active compounds (1-3) was determined using
A L Okunade et al.
Planta medica, 65(5), 447-448 (1999-07-27)
An ethanolic extract of the aerial parts of Mitracarpus scaber demonstrated good antimicrobial activity. Bioassay directed fractionation of this extract led to the isolation of benz[g]isoquinoline-5,10-dione (1) as an active component. Compound 1 showed significant in vitro inhibitory activity against
Ekaterina Shinkevich et al.
Organic & biomolecular chemistry, 9(2), 538-548 (2010-10-27)
1,2-Disubstituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones are prepared for the first time through an activated Pictet-Spengler reaction of the corresponding imines of 2-(1,4-dimethoxynaphth-2-yl)ethylamine in the presence of an acyl chloride and AlCl(3) followed by an oxidation with silver(II) oxide in nitric acid. Depending on
B T Walton et al.
Science (New York, N.Y.), 222(4622), 422-423 (1983-10-28)
Morphological abnormalities including extra compound eyes, extra heads, and distally duplicated legs were generated in cricket embryos by treating eggs with single doses of either benz[g]isoquinoline-5,10-dione or benzo[h]quinoline-5,6-dione. Slight structural modifications of the molecules resulted in a loss of teratogenic
Andrew Jonathan Nok
Cell biochemistry and function, 20(3), 205-212 (2002-07-19)
An ethanolic extract of Mitracarpus scaber was found to possess in vitro and in vivo trypanocidal activity against Trypanosoma congolense. At a dosage of 50 mg kg(-1) day(-1) in normal saline for 5 days, the extract cured Balbc mice infected

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