171522-36-4

Usage

InChI:InChI=1/C15H14O3/c1-15(2)7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-8-15/h3-6H,7-8H2,1-2H3

Upstream product

• 138779-68-7 2-(3-hydroxy-2,2-dimethylpropyl)-1,4-naphthoquinone 
• 35896-55-0 2-Methyl-1,3,4-trimethoxynaphthalene 
• 777075-01-1 3-bromomethyl-1,2,4-trimethoxynaphthalene 
• 777075-05-5 ethyl 2,2-dimethyl-3-(1,3,4-trimethoxynaphthalen-2-yl)propionate 
• 777075-25-9 2,2-dimethyl-3-(1,3,4-trimethoxynaphthalen-2-yl)propan-1-ol 
• 60683-53-6 1,2,4-trimethoxynaphthalene 
• 138779-67-6 1-hydroxy-β,β-dimethyl-2-naphthalenepropanol 

Relevant academic research and scientific papers

Studies on the oxidative cyclization of 3-hydroxyalkyl-1,2,4- trialkoxynaphthalenes and synthetic application for the biologically active natural compound rhinacanthone

The oxidative intramolecular cyclization of 3-hydroxyalkyl-1,2,4- trimethoxynaphthalenes was investigated. A series of 1,2-naphthoquinone fused cyclic ethers were synthesized directly from 3-hydroxyalkyl-1,2,4- trimethoxynaphthalenes by exposure to diammonium cerium (IV) nitrate. To understand the reaction mechanism, the intramolecular cyclization of 3-hydroxyalkyl-naphthoquinones that were formed as reaction intermediates was also examined. The results suggested that the reaction proceeds by a stepwise oxidation-cyclization mechanism. Using this methodology, five-step synthesis of rhinacanthone was achieved with high yield.

Transforming rhinacanthin analogues from potent anticancer agents into potent antimalarial agents

Twenty-six novel naphthoquinone aliphatic esters were synthesized by esterification of 1,4-naphthoquinone alcohols with various aliphatic acids. The 1,4-naphthoquinone alcohols were prepared from 1-hydroxy-2-naphthoic acid in nine steps with excellent yields. Twenty-four of the novel synthetic naphthoquinone esters showed significant antimalarial activity with IC 50 values in the range of 0.03-16.63 μM. The length of the aliphatic chain and the presence of C-2′ substituents on the propyl chain affected the activity. Interestingly, compounds 31 and 37 showed very good antimalarial activity and were not toxic to normal Vero cells, and the PTI values of 31 (> 1990.38) and 37 (1825.94) are excellent. Both 31 and 37 showed potent inhibition against P. falciparum 3D7 cyt bc1 and no inhibition on rat cyt bc1. They showed IC50 values in the nanomolar range, providing full inhibition of cyt bc1 with one molecule inhibitor bound per cyt bc1 monomer at the Qo site.

Potent antitumor activity of synthetic 1,2-naphthoquinones and 1,4-naphthoquinones

Rhinacanthone (1) and two 1,2-pyranonaphthoquinones (2,3) were synthesized and found to show very potent cytotoxicity against three cancer cell lines (KB, HeLa and HepG2) with IC50 values of 0.92-9.63 μM, whereas the corresponding hydroxylated derivative 4 had reduced cytotoxicity (IC50 values of 7.61-24.13 μM). Three 1,2-furanonaphthoquinone derivatives (5-7) were also synthesized with similar cytotoxicity as 1,2-pyranonaphthoquinones. In comparison to 1,2-naphthoquinones, six 1,4-naphthoquinones derivatives fused with pyran ring (8-10) and furan ring (11-13) were synthesized and they showed less cytotoxicity or inactive to the cancer cell lines. Moreover, compound 13 had significant cytotoxicity against HeLa cell line (IC50 value of 9.25 μM) while it showed no toxic to vero cell.