1,8-Dihydroxy-4,5-dinitroanthraquinone

Names

[ CAS No. ]:
81-55-0

[ Name ]:
1,8-Dihydroxy-4,5-dinitroanthraquinone

[Synonym ]:
4,5-Dinitrochrysazin
1,8 DIHYDROXY 4,5 DINITRO AQ
4,5-Dinitrodanthron
1,8-dihydroxy-4,5-dinitroanthra-9,10-quinone
1,8-dihydroxy-4,5-dinitro-anthraquinon
Dihydroxy-4,5-dinitroanthraquinone
MFCD00019149
1,8-Dihydroxy-4,5-dinitroanthracene-9,10-dione
1,8-Dihydroxy-4,5-dinitro-anthrachinon
1,8-dihydroxy-4,5-dinitro-anthraquinone
1,8-dihydroxy-4,5-dinitro-9,10-anthracenedione
EINECS 201-360-3
1,8-Dihydroxy-4,5-dinitro-9,10-anthraquinone
1,8-Dihydroxy-4,5-di
9,10-Anthracenedione, 1,8-dihydroxy-4,5-dinitro-
4,5 DINITROCHRYSAZINE
4,5-dinitro-1,8-dihydroxyanthraquinone

Biological Activity

[Description]:

1,8-Dihydroxy-4,5-dinitroanthraquinone (ARDP0006; DHDNE) is a potent inhibitor of serine proteinase NS2B/3, the dengue viral protein. 1,8-Dihydroxy-4,5-dinitroanthraquinone has intermolecular proteinase activity and viral inhibition ability with IC50s of 432 μM and 4.2 μM, respectively. Meanwhile 1,8-Dihydroxy-4,5-dinitroanthraquinone inhibits NS2B/3 cleavage in BHK-21 cells at a dose ranging from 4.2 μM to 432 μM[1].

[Related Catalog]:

Research Areas >> Infection

[In Vitro]

1,8-Dihydroxy-4,5-dinitroanthraquinone (50 μM-2 mM；90 分钟) 抑制 NS2B/3 裂解，并在 100 μM 时显着且显着地作用于 BHK-21 细胞[1]。

[References]

[1]. Constant DA, et al. Targeting intramolecular proteinase NS2B/3 cleavages for trans-dominant inhibition of dengue virus. Proc Natl Acad Sci U S A. 2018 Oct 2;115(40):10136-10141.

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
669.4±55.0 °C at 760 mmHg

[ Melting Point ]:
225 °C (dec.)(lit.)

[ Molecular Formula ]:
C₁₄H₆N₂O₈

[ Molecular Weight ]:
330.206

[ Flash Point ]:
280.8±20.0 °C

[ Exact Mass ]:
330.012421

[ PSA ]:
166.24000

[ LogP ]:
4.94

[ Vapour Pressure ]:
0.0±2.1 mmHg at 25°C

[ Index of Refraction ]:
1.782

[ Stability ]:
Stable. Incompatible with strong oxidizing agents.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CB6700000

CHEMICAL NAME :: Anthraquinone, 1,8-dihydroxy-4,5-dinitro-

CAS REGISTRY NUMBER :: 81-55-0

BEILSTEIN REFERENCE NO. :: 2182054

LAST UPDATED :: 199710

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C14-H6-N2-O8

MOLECULAR WEIGHT :: 330.22

WISWESSER LINE NOTATION :: L C666 BVIVJ DQ GNW KNW NQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 180 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 10 ug/plate

REFERENCE :: ENMUDM Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For publisher information, see EMMUEG. Volume(issue)/page/year: 9(Suppl 9),1,1987

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
CB6700000

[ HS Code ]:
2914700090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914700090

[ Summary ]:
HS: 2914700090 halogenated, sulphonated, nitrated or nitrosated derivatives of ketones and quinones, whether or not with other oxygen function Tax rebate rate:9.0% Supervision conditions:none VAT:17.0% MFN tariff:5.5% General tariff:30.0%

Articles

Catalysed hydrogenation of hydroxynitroanthraquinones in strong acid. Morley JO and Hutcheson R.

J. Chem. Technol. Biotechnol. 30(1) , 409-414, (1980)

Measurement and Correlation of Derivatized Anthraquinone Solubility in Supercritical Carbon Dioxide. Alwi RS and Tamura K.

J. Chem. Eng. Data 60(10) , 3046-3052, (2015)