14554-09-7

Basic information

• Product Name: 5,8-Dihydroxy-2-methyl-1,4-naphthoquinone
• Synonyms: 2-Methyl-5,8-dihydroxy-1,4-naphthoquinone;2-Methylnaphthazarin;5,8-Dihydroxy-2-methyl-1,4-naphthoquinone
• CAS NO: 14554-09-7
• Molecular Formula: C11H8 O4
• Molecular Weight: 204.1788
• Mol File: 14554-09-7.mol
• Article Data: 8

Chemical Properties

• Melting Point: 173 °C
• Boiling Point: 484.3°Cat760mmHg
• Flash Point: 260.8°C
• Appearance: /
• Density: 1.486g/cm³
• Vapor Pressure: 5.28E-10mmHg at 25°C
• Refractive Index: 1.67
• PKA: 7.39±0.20(Predicted)
• CAS DataBase Reference: 5,8-Dihydroxy-2-methyl-1,4-naphthoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 5,8-Dihydroxy-2-methyl-1,4-naphthoquinone(14554-09-7)
• EPA Substance Registry System: 5,8-Dihydroxy-2-methyl-1,4-naphthoquinone(14554-09-7)

Safety Data

• Hazardous Substances Data: 14554-09-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H8O4/c1-5-4-8(14)9-6(12)2-3-7(13)10(9)11(5)15/h2-4,12-13H,1H3

Upstream product

• 616-02-4 citraconic acid anhydride 
• 150-78-7 1,4-dimethoxybezene 
• 124484-51-1 6-Formyl-5-hydroxy-1,4-dimethoxynaphthalin 
• 124470-58-2 5-Hydroxy-1,4-dimethoxy-6-methylnaphthalin 
• 91963-30-3 5,8-dimethoxynaphthalen-1-ol 
• 481-42-5 5-hydroxy-2-methyl-1,4-naphthoquinone 
• 86432-50-0 5,8-dimethoxy-3-methyl-1,4-naphthaquinone 
• 125247-56-5 2-methyl-1,5-dinitro-naphthalene 
• 14597-09-2 diacetato de 2-metilnaftazarina 
• 123-31-9 hydroquinone 
• 108-31-6 maleic anhydride 
• 95-71-6 2-methylbenzene-1,4-diol 
• 5196-28-1 juglone acetate 

Relevant articles and documents

Identification of quinones as novel PIM1 kinase inhibitors

PIM1 is a proto-oncogene encoding the serine/threonine PIM1 kinase. PIM1 kinase plays important roles in regulating aspects of cell cycle progression, apoptosis resistance, and has been implicated in the development of such malignancies as prostate cancer and acute myeloid leukemia among others. Knockout of PIM1 kinase in mice has been shown to be non-lethal without any obvious phenotypic changes, making it an attractive therapeutic target. Our investigation of anthraquinones as kinase inhibitors revealed a series of quinone analogs showing high selectivity for inhibition of the PIM kinases. Molecular modeling studies were used to identify key interactions and binding poses of these compounds within the PIM1 binding pocket. Compounds 1, 4, 7 and 9 inhibited the growth of DU-145 prostate cancer cell lines with a potency of 8.21 μM, 4.06 μM, 3.21 μM and 2.02 μM.

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PROTEIN KINASE INHIBITORS

The present disclosure relates to compounds that act as protein kinase inhibitors, and the synthesis of the same. Further, the present disclosure teaches the utilization of such compounds in a treatment for proliferative diseases, including cancer, particularly breast cancer, and especially ER+ and/or HER2+ breast cancer.

Preparation of naphthoquinone derivatives from plumbagin and their ichthyotoxicity

Various naphthoquinone derivatives were prepared from a natural product, 5-hydroxy-2-methyl-1,4-naphthoquinone (plumbagin); these were mostly substituted at C-3 through carbon-carbon bond formation mediated by a metal- based oxidant such as lead tetraacetate in the presence of various carboxylic acids. The halogenated compounds showed stronger ichthyotoxicity than plumbagin, but other derivatives were less active.