1,4-Naphthalenedione,2,3-dichloro-5,8-dihydroxy-
Product Information
Molecular Formula
C10H4 Cl2 O4
Molecular Weight
259.04
Description
1,4-Naphthalenedione,2,3-dichloro-5,8-dihydroxy- is a potent biomedical agent recognized for its anti-cancer properties. Primarily, it is used in the formulation of drugs for treating patients with prostate cancer.
Synonyms
2,3-DICHLORO-5,8-DIHYDROXY-1,4-NAPHTHOQUINONE; 2,3-DICHLORO-5,8-DIHYDROXY-1,4-NAPHTOQUINONE; NA; RARECHEM AR PA 0036; 2,3-DICHLORO-5,8-DIHYDROXY-1,4-NAPHTOQUINONE 95+%; 2,3-DICHLORO-5,8-DIHYDROXY-1,4-NAPTHOQUINONE
IUPAC Name
6,7-dichloro-5,8-dihydroxynaphthalene-1,4-dione
SMILES
C1=CC(=O)C2=C(C1=O)C(=C(C(=C2O)Cl)Cl)O
InChI
InChI=1S/C10H4Cl2O4/c11-7-8(12)10(16)6-4(14)2-1-3(13)5(6)9(7)15/h1-2,15-16H
InChI Key
KFAVXUQFBGHURZ-UHFFFAOYSA-N
Boiling Point
540.4°C at 760mmHg
Melting Point
197-199°C(lit.)
Flash Point
Not applicable
Purity
95%
Density
1.807g/cm3
Appearance
dark purple powder
Safety Information
Hazards
H302 + H312 + H332 - H315 - H319 - H335
Precautionary Statement
P280 - P301 + P312 + P330 - P302 + P352 + P312 - P304 + P340 + P312 - P305 + P351 + P338
Computed Properties
XLogP3
3.1
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
0
Exact Mass
257.9486640 g/mol
Monoisotopic Mass
257.9486640 g/mol
Topological Polar Surface Area
74.6Ų
Heavy Atom Count
16
Formal Charge
0
Complexity
334
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| CN-113652716-A | Process for electrolyzing high-nickel copper anode by adopting periodic reverse current | 2021-09-13 |
| CN-112961163-A | High-capacity metal ion battery organic electrode material and preparation method and application thereof | 2021-01-29 |
| CN-112057440-A | Medical application of 1, 4-naphthoquinone derivative | 2020-09-25 |
| JP-2022016389-A | Soil conditioner and its use | 2020-07-08 |
| WO-2022009955-A1 | Soil conditioner and use thereof | 2020-07-08 |
| US-2021144998-A1 | Compositions and methods for treating huanglongbing disease in citrus | 2019-11-15 |
| WO-2021097410-A1 | Compositions and methods for treating huanglongbing disease in citrus | 2019-11-15 |
| JP-2019183074-A | Radical curable composition | 2018-04-16 |
| US-2021020943-A1 | Redox Flow Battery Electrolytes | 2018-02-13 |
| KR-20190063669-A | Thermoplastic polyester resin composition having good color and heat resistance | 2017-11-30 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 30996770 | 2019-04-11 | Discovery of 1,4-Naphthoquinones as a New Class of Antiproliferative Agents Targeting GPR55 | ACS medicinal chemistry letters |
| 23037165 | 2012-01-01 | Leishmanicidal activity of two naphthoquinones against Leishmania donovani | Biological & pharmaceutical bulletin |
| 19046417 | 2008-12-01 | Caspase-3-mediated cleavage of p65/RelA results in a carboxy-terminal fragment that inhibits IkappaBalpha and enhances HIV-1 replication in human T lymphocytes | Retrovirology |
| 18924186 | 2008-01-01 | Valence-state analysis through spectroelectrochemistry in a series of quinonoid-bridged diruthenium complexes [(acac)(2)Ru(mu-L)Ru(acac)(2)](n) (n=+2, +1, 0, -1, -2) | Chemistry (Weinheim an der Bergstrasse, Germany) |
| 14644418 | 2003-12-04 | Involvement of Akt in mitochondria-dependent apoptosis induced by a cdc25 phosphatase inhibitor naphthoquinone analog | FEBS letters |
| 12785737 | 2003-05-01 | Effects of a naphthoquinone analog on tumor growth and apoptosis induction | Archives of pharmacal research |
| 12095638 | 2002-07-03 | Induction of p73beta by a naphthoquinone analog is mediated by E2F-1 and triggers apoptosis in HeLa cells | FEBS letters |
| 11320092 | 2001-07-06 | Caspase-3-mediated cleavage of the NF-kappa B subunit p65 at the NH2 terminus potentiates naphthoquinone analog-induced apoptosis | The Journal of biological chemistry |
