15448-58-5

Basic information

• Product Name: 1A,7A-DIHYDRONAPHTHO[2,3-B]OXIRENE-2,7-DIONE
• Synonyms: 2,3-EPOXY-2,3-DIHYDRO-1,4-NAPHTHOQUINONE;1A,7A-DIHYDRONAPHTHO[2,3-B]OXIRENE-2,7-DIONE;AKOS MSC-0135;Naphth[2,3-b]oxirene-2,7-dione, 1a,7a-dihydro- (9CI);11-Oxatricyclo[8.1.0.03,8]undecane-3(8),4,6-triene-2,9-dione;1a,2,7,7a-Tetrahydronaphtho[2,3-b]oxirene-2,7-dione;1a,7a-Dihydronaphth[2,3-b]oxirene-2,7-dione;2,3-Epoxytetralin-1,4-dione
• CAS NO: 15448-58-5
• Molecular Formula: C₁₀H₆O₃
• Molecular Weight: 174.15
• EINECS: 239-465-1
• Product Categories: EPOXYDE
• Mol File: 15448-58-5.mol
• Article Data: 31

Chemical Properties

• Melting Point: 133-134 °C
• Boiling Point: 377.8°Cat760mmHg
• Flash Point: 173.9°C
• Appearance: /
• Density: 1.462g/cm³
• Vapor Pressure: 6.57E-06mmHg at 25°C
• Refractive Index: 1.641
• CAS DataBase Reference: 1A,7A-DIHYDRONAPHTHO[2,3-B]OXIRENE-2,7-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1A,7A-DIHYDRONAPHTHO[2,3-B]OXIRENE-2,7-DIONE(15448-58-5)
• EPA Substance Registry System: 1A,7A-DIHYDRONAPHTHO[2,3-B]OXIRENE-2,7-DIONE(15448-58-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 15448-58-5(Hazardous Substances Data)

Usage

General Description

1A,7A-Dihydronaphtho[2,3-b]oxirene-2,7-dione is a chemical compound that is a derivative of naphthalene. It is a cyclic compound with two oxygen atoms in its structure, and it is used as a starting material in the synthesis of various organic compounds. It has potential applications in the field of organic chemistry and pharmaceutical research. 1A,7A-DIHYDRONAPHTHO[2,3-B]OXIRENE-2,7-DIONE has structural properties that make it suitable for use as a building block in the development of new drugs and materials. Its chemical structure and reactivity make it an important target for chemical synthesis and research efforts.

InChI:InChI=1/C10H6O3/c11-7-5-3-1-2-4-6(5)8(12)10-9(7)13-10/h1-4,9-10H

Upstream product

• 130-15-4 [1,4]naphthoquinone 
• 91-20-3 naphthalene 
• 1077-72-1 4-Diazobenzo-2,5-cyclohexadienone 
• 571-60-8 1,4-Dihydroxynaphthalene 

Downstream Products

• 21720-68-3 2-(phenylamino)-4-(phenylimino)-1(4H)-naphthalenone 
• 54941-03-6 2-hydroxy-3-(phenylamino)naphthalene-1,4-dione 
• 122822-61-1 4-(phenylazo)-1,2-naphthalenediol 
• 16432-90-9 4-(3,4-dihydroxy-phenyl-trans-azo)-benzenesulfonic acid 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 131762-85-1 4-(4-nitro-phenylazo)-naphthalene-1,2-diol 
• 135330-11-9 2-hydroxy-3-p-toluidino-[1,4]naphthoquinone 
• 27828-56-4 4-(phenylamino)naphthalene-1,2-dione 
• 1526-73-4 3-chloro-2-hydroxy-naphthalene-1,4-dione 
• 1236-39-1 2-oxy-3-(isoquinolinium-2'-yl)-1,4-naphthoquinone 
• 485-47-2 indan-1,2,3-trione hydrate 
• 605-37-8 isonaphthazarine 
• 528-46-1 phthalonic acid 
• 130-15-4 [1,4]naphthoquinone 

Relevant articles and documents

Reactions of peroxynitrite with N,N-dimethyl-p-toluidine and 1,4-naphthoquinone. Evidence for heterolytic cleavage of a nitrogen-oxygen bond in peroxynitrous acid

Peroxynitrite (ONOO-) has been found to react with the title amine 1 and quinone 5 to form N-nitrosoamine 2 and 2,3-epoxide 6, respectively, in accord with the in situ generation of the nitrosonium and hydroperoxide ions as the respective reactive species.

Bioactivity profiles of cytoprotective short-chain quinones

Short-chain quinones (SCQs) have been investigated as potential therapeutic candidates against mitochondrial dysfunction, which was largely thought to be associated with the reversible redox characteristics of their active quinone core. We recently reported a library of SCQs, some of which showed potent cytoprotective activity against the mitochondrial complex I inhibitor rotenone in the human hepatocarcinoma cell line HepG2. To better characterize the cytoprotection of SCQs at a molecular level, a bioactivity profile for 103 SCQs with different compound chemistries was generated that included metabolism related markers, redox activity, expression of cytoprotective proteins and oxidative damage. Of all the tested endpoints, a positive correlation with cytoprotection by SCQs in the presence of rotenone was only observed for the NAD(P)H:quinone oxidoreductase 1 (NQO1)-dependent reduction of SCQs, which also correlated with an acute rescue of ATP levels. The results of this study suggest an unexpected mode of action for SCQs that appears to involve a modification of NQO1-dependent signaling rather than a protective effect by the reduced quinone itself. This finding presents a new selection strategy to identify and develop the most promising compounds towards their clinical use.

Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase

Schistosomiasis ranks second only to malaria as the most common parasitic disease worldwide. 700 million people are at risk and 240 million are already infected. Praziquantel is the anthelmintic of choice but decreasing efficacy has already been documented. In this work, we exploited the inhibition of Schistosoma mansoni dihydroorotate dehydrogenase (SmDHODH) as a strategy to develop new therapeutics to fight schistosomiasis. A series of quinones (atovaquone derivatives and precursors) was evaluated regarding potency and selectivity against both SmDHODH and human DHODH. The best compound identified is 17 (2-hydroxy-3-isopentylnaphthalene-1,4-dione) with IC50 = 23 ± 4 nM and selectivity index of 30.83. Some of the new compounds are useful pharmacological tools and represent new lead structures for further optimization.

Synthesis, anti-proliferative activity evaluation and 3D-QSAR study of naphthoquinone derivatives as potential anti-colorectal cancer agents

Colorectal cancer (CRC) is a disease with high incidence and mortality, constituting the fourth most common cause of death from cancer worldwide. Naphthoquinones are attractive compounds due to their biological and structural properties. In this work, 36 naphthoquinone derivatives were synthesized and their activity evaluated against HT-29 cells. Overall, high to moderate anti-proliferative activity was observed in most members of the series, with 15 compounds classified as active (1.73 50 2 = 0.99 and q2 = 0.625). This model allowed proposing five new compounds with two-fold higher theoretical anti-proliferative activity, which would be worthwhile to synthesize and evaluate. Further investigations will be needed to determine the mechanism involved in the effect of most active compounds which are potential candidates for new anticancer agents.