3343-38-2Relevant articles and documents
Molluscicidal activity of synthetic lapachol amino and hydrogenated derivatives
Silva, Tania M.S.,Camara, Celso A.,Barbosa, Ticiano P.,Soares, André Z.,Da Cunha, Luciana C.,Pinto, Angelo C.,Vargas, Maria D.
, p. 193 - 196 (2005)
A series of new amino derivatives and a new partially hydrogenated derivative of the natural naphthoquinone lapachol were found to exhibit molluscicidal activity against Biomphalaria glabrata. A series of new amino derivatives and a new partially hydrogenated derivative of the natural naphthoquinone lapachol were assayed for molluscicidal activity against Biomphalaria glabrata. These derivatives showed low to medium LC50 values, and a 3.1 μg/mL value for the most potent derivative of the series. The toxicity is in agreement with the decrease of polar character of the tested compounds.
Dudley,Chiang
, p. 120,125 (1969)
Gas-phase reactivity of 2-hydroxy-1,4-naphthoquinones: A computational and mass spectrometry study of lapachol congeners
Vessecchi, Ricardo,Emery, Flávio S.,Galembeck, Sérgio E.,Lopes, Norberto P.
, p. 1648 - 1659 (2012)
In order to understand the influence of alkyl side chains on the gas-phase reactivity of 1,4-naphthoquinone derivatives, some 2-hydroxy-1,4-naphthoquinone derivatives have been prepared and studied by electrospray ionization tandem mass spectrometry in combination with computational quantum chemistry calculations. Protonation and deprotonation sites were suggested on the basis of gas-phase basicity, proton affinity, gas-phase acidity (?G acid), atomic charges and frontier orbital analyses. The nature of the intramolecular interaction as well as of the hydrogen bond in the systems was investigated by the atoms-in-molecules theory and the natural bond orbital analysis. The results were compared with data published for lapachol (2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone). For the protonated molecules, water elimination was verified to occur at lower proportion when compared with side chain elimination, as evidenced in earlier studies on lapachol. The side chain at position C(3) was found to play important roles in the fragmentation mechanisms of these compounds.
Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase
Calil, Felipe A.,David, Juliana S.,Chiappetta, Estela R.C.,Fumagalli, Fernando,Mello, Rodrigo B.,Leite, Franco H.A.,Castilho, Marcelo S.,Emery, Flavio S.,Nonato, M.Cristina
, p. 357 - 366 (2019/02/19)
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 and evaluation of quinonoid compounds against tumor cell lines
Da Silva Jr., Eufranio N.,Cavalcanti, Bruno C.,Guimar?es, Tiago T.,Pinto, Maria Do Carmo F.R.,Cabral, Igor O.,Pessoa, Cláudia,Costa-Lotufo, Letícia V.,De Moraes, Manoel O.,De Andrade, Carlos K.Z.,Dos Santos, Marcelo R.,De Simone, Carlos A.,Goulart, Marilia O.F.,Pinto, Antonio V.
scheme or table, p. 399 - 410 (2011/02/27)
Thirty two compounds were synthesized in moderate to high yields and showed activity against cancer cells HL-60 (leukemia), MDA-MB435 (melanoma), HCT-8 (colon) and SF295 (central nervous system), with IC50 below 2 μM for some compounds. The β-lapachone-based 1,2,3-triazoles showed the best cytoxicity profile and emerge as promising anticancer prototypes. Insights about the reactive oxygen species (ROS) mechanism of anticancer action for some compounds were obtained by addition of 1-bromoheptane that deplete reduced glutathione (GSH) content and by using N-acetylcysteine that protects cells against apoptotic cellular death, as well by analysis of thiobarbituric acid reactive substances (TBARS) formation, and oxidative DNA damage after treatment detected by the comet assay with the bacterial enzymes formamidopyrimidine DNA-glycosylase (FPG) and endonuclease III (ENDOIII).
