68707-65-3Relevant academic research and scientific papers
Photoinduced benzylation of 1,4-dimethoxynaphthalene by benzyl halides
Albini, Angelo,Siviero, Enrico,Mella, Mariella,Long, Conor,Pratt, Albert
, p. 1895 - 1900 (1995)
Irradiation of 1,4-dimethoxynaphthalene (DMNH) in the presence of 4-substituted benzyl chlorides (X-C6H4CH2Cl, X=H, Cl, CN or NO2) in the either acetonitrile or benzene solution results in benzylation of DNNH, predominantly at position 2 and to a lesser extent on the unsubstituted ring.Steady-state and flash photolysis studies show that charge transfer between singlet excited DMNH and the chlorides is involved.The reaction occurs predominantly in-cage via concerted electron transfer and carbon-chlorine bond cleavage with X=H or Cl, while with X=NO2 fragmentation of the benzyl chloride radical anion occurs out-of-cage, but the process in this case is much less efficient due to competing back electron transfer.
Cytotoxicity of lapachol, β-lapachone and related synthetic 1,4-naphthoquinones against oesophageal cancer cells
Sunassee, Suthananda N.,Veale, Clinton G.L.,Shunmoogam-Gounden, Nelusha,Osoniyi, Omalaja,Hendricks, Denver T.,Caira, Mino R.,De La Mare, Jo-Anne,Edkins, Adrienne L.,Pinto, Antonio V.,Da Silva Junior, Eufranio N.,Davies-Coleman, Michael T.
, p. 98 - 110 (2013/05/09)
Naphthoquinones have been found to have a wide range of biological activities, including cytotoxicity to cancer cells. The secondary metabolites lapachol, α- and β-lapachone and a series of 25 related synthetic 1,4-naphthoquinones were screened against the oesophageal cancer cell line (WHCO1). Most of the compounds exhibited enhanced cytotoxicity (IC50 1.6-11.7 μM) compared to the current drug of choice cisplatin (IC 50 = 16.5 μM). This study also established that the two new synthetic halogenated compounds 12a and 16a (IC50 = 3.0 and 7.3 μM) and the previously reported compound 11a (IC50 = 3.9 μM), were non-toxic to NIH3T3 normal fibroblast cells. Cell death of oesophageal cancer cells by processes involving PARP cleavage caused by 11a was shown to be associated with elevated c-Jun levels, suggesting a role for this pathway in the mechanism of action of this cohort of naphthoquinone compounds.
The synthesis of radermachol
Joshi,Jiang,Rho,Pelletier
, p. 8220 - 8232 (2007/10/02)
Five different approaches to the preparation of 6,7-benzo-3,4-(1,4-dimethoxy-2,3-naphtho)-1,5-dioxosuberane (3), an intermediate needed for the synthesis of radermachol (1), the red pigment from the roots of Radermachera xylocarpa, are described. The synthesis of radermachol (1) has been accomplished from 1,4-naphthoquinone in 14 steps.
The Total Synthesis of Radermachol
Jiang, Qingping,Joshi, Balawant S.,Pelletier, William S.
, p. 5283 - 5286 (2007/10/02)
The red pigment, radermachol (1), has been synthesized from 1,4-dimethoxynaphthalene in thirteen steps.
