14554-09-7

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

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

Relevant academic research and scientific papers

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.

NMR Studies of Intramolecular Proton Exchange in Alkylated Naphthazarins

Three groups of alkyl-substituted naphthazarins were studied by 1H and 13C NMR in chloroform-d at ambient temperature.Preliminary 1H NMR studies were carried out on selected members of each group at low temperatures (down to-120 deg C) in dichloromethane-d2 solutions.Monoalkylnaphthazarins were found to exist predominatly as the 2-alkyl tautomers (I) and the dimethylalkyl species as the 2,3-dimethyl-6-alkyl tautomers (I).However, both symmetrically and unsymmetrically substituted 2,6- and 2,7-dialkylnaphthazarins exhibited averaged chemical shifts and coupling constants indicating rapid proton exhange between the two minimum energy 1,4-dione tautomers (I and II). 13C NMR shifts were utilized to calculate tautomer populations of the unsymmetrical 2,6- and 2,7-(methyl, alkyl)naphthazarins.KEY WORDS 1H NMR 13C NMR Intramolecular proton exhange Alkylated naphthazarins

1,4-Naphthoquinones, XIX: 2-, 3- and 6-Methyljuglone from Formylnaphthol Derivatives

The methylnaphthol derivatives 9 and 10 are suitable compounds for the synthesis of plumbagin, 6-methyljuglone (14) and 3-methylnaphthazarine (12). 9 and 10 are derived from 5 and 6 which are synthesized by formylation of the naphthols 2 and 3.As it was not possible to get the formylnaphthol 8 in the same way, isoplumbagin (18) was prepared by bromine-lithium exchange in the key compound 16 followed by methylation and oxidation.

PROTEIN KINASE INHIBITORS AND USE THEREOF FOR TREATMENT OF NEIMODEGENERATIVE DISEASES

The present disclosure relates to compounds that act as protein kinase inhibitors, especially CK1δ and/or CK1ε inhibitors, which can be used to treat a serine/threonine kinase-dependent disease and condition, such as neurodegenerative diseases like Alzheimer's Disease, and the synthesis of the same. Further, the present disclosure teaches the utilization of such compounds in a treatment for neurodegenerative diseases, including Alzheimer's disease.

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.

Synthesis of naphthazarin derivatives and identification of novel thioredoxin reductase inhibitor as potential anticancer agent

Mammalian thioredoxin reductase (TrxR) enzymes play a crucial role in regulating multiple redox-based signaling pathways and have attracted increasing attention as promising anticancer drug targets. We report here the synthesis of a panel of naphthazarin derivatives and discovery of 2-methyl-5,8-dihydroxy-1,4-naphthoquinone (3, 2-methylnaphthazarin) as a potent cytotoxic agent with a submicromolar half maximal inhibitory concentration to the human promyelocytic leukemia HL-60 cells. Mechanism studies reveal that the compound selectively inhibits TrxR to induce oxidative stress-mediated apoptosis of HL-60 cells. Knockdown of TrxR sensitizes the cells to 3 insults, while overexpression of the functional enzyme confers resistance to the compound treatment, underpinning the physiological significance of targeting TrxR by 3. Clarification of the interaction of compound 3 with TrxR unveils a mechanism underlying the cellular action of the compound, and sheds light in considering development of the compound as a potential cancer chemotherapeutic agent.

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.