1201786-14-2Relevant academic research and scientific papers
A new approach for the synthesis of 3-substituted cytotoxic nor-β-lapachones
Cardoso, Mariana F. C.,Da Silva, Illana M. C. B.,Dos Santos Jr., Helve?cio M.,Rocha, David R.,Arau?jo, Ana Je?rsia,Pessoa, Claudia,De Moraes, Manoel O.,Lotufo, Leti?cia V. C.,De C. Da Silva, Fernando,Santos, Wilson C.,Ferreira, Vitor F.
, p. 12 - 16 (2013/05/08)
Several studies have demonstrated the cytotoxic potential of nor-β-lapachone derivative against cancer cells. Considering nor-β-lapachone as an important prototype, a set of new 3-substituted nor-β-lapachones was synthesized by a new synthetic route that involves the use of synthetic intermediate generated for coupling with several nucleophiles containing the carbohydrate and 2H-pyrazole substituent moieties. All the compounds were screened against four tumor cell lines. Two of the compounds showed moderate cytotoxicity, while the other compounds strongly inhibit all tested cancer cell lines.
Potent antileukemic action of naphthoquinoidal compounds: Evidence for an intrinsic death mechanism based on oxidative stress and inhibition of DNA repair
Cavalcanti, Bruno C.,Cabral, Igor O.,Rodrigues, Felipe A. R.,Barros, Francisco W. A.,Rocha, Danilo D.,Magalha?es, Hemerson I. F.,Moura, Dinara J.,Saffi, Jenifer,Henriques, Joa?o A. P.,Carvalho, Tatiane S. C.,Moraes, Manoel O.,Pessoa, Cla?udia,De Melo, Isadora M. M.,Da Silva Jr., Eufra?nio N.
, p. 145 - 163 (2013/05/08)
The current study describes that nor-β-lapachone and its arylamino derivatives, iodinated and methylated naphthoquinones and nor-β-lapachone- based 1,2,3-triazoles exhibited pronounced cytotoxic effects against four human leukemia cell lines (HL-60, K562, Molt-4 and Jurkat). Nor-β-lapachones arylamino substituted with potent activity were identified, revealing themselves as potential prototypes against tumor cell lines. Moreover, cells treated with these compounds showed DNA damage according to the standard comet assay, a finding that was, at least in part, due to increased intracellular levels of ROS. HL-60 cells were chosen to study the underlying molecular mechanisms of cytotoxicity. Drug-induced apoptosis in HL-60 cells was observed by flow cytometry analyses. Strains of Saccharomyces cerevisiae were used for a preliminary investigation into the mechanism of drug action on DNA topoisomerases. These results suggested that the cytotoxicity of these compounds apparently does not involve topoisomerase inhibition, but that treatment impairs DNA repair activity, thus triggering cell death. Considering their pro-oxidant properties, we investigated the ability of these compounds to induce apoptosis and chromosomal aberrations as micronuclei in Chinese hamster lung fibroblasts (V79 cells). Morphological apoptotic nuclei and micronuclei induction following drug treatment were observed, suggesting a correlation between DNA damage and apoptosis.
3-Arylamino and 3-alkoxy-nor-β-lapachone derivatives: Synthesis and cytotoxicity against cancer cell lines
Da Silva Jr., Eufranio N.,De Deus, Clara F.,Cavalcanti, Bruno C.,Pessoa, Cláudia,Costa-Lotufo, Letícia V.,Montenegro, Raquel C.,De Moraes, Manoel O.,Pinto, Maria Do Carmo F. R.,De Simone, Carlos A.,Ferreira, Vitor F.,Goulart, Marilia O. F.,Andrade, Carlos Kleber Z.,Pinto, Ant?nio V.
experimental part, p. 504 - 508 (2010/05/02)
Several 3-arylamino and 3-alkoxy-nor-β-lapachone derivatives were synthesized in moderate to high yields and found to be highly potent against cancer cells SF295 (central nervous system),HCT8 (colon), MDA-MB435 (melanoma), and HL60 (leukemia), with ICsub
The evaluation of quinonoid compounds against Trypanosoma cruzi: Synthesis of imidazolic anthraquinones, nor-β-lapachone derivatives and β-lapachone-based 1,2,3-triazoles
da Silva Júnior, Eufranio N.,Guimar?es, Tiago T.,Menna-Barreto, Rubem F.S.,Pinto, Maria do Carmo F.R.,de Simone, Carlos A.,Pessoa, Claudia,Cavalcanti, Bruno C.,Sabino, José R.,Andrade, Carlos Kleber Z.,Goulart, Marilia O.F.,de Castro, Solange L.,Pinto, Ant?nio V.
scheme or table, p. 3224 - 3230 (2010/07/08)
In continuing our screening program of naphthoquinone activity against Trypanosoma cruzi, the aetiological agent of Chagas' disease, new β-lapachone-based 1,2,3-triazoles, 3-arylamino-nor-β-lapachones, 3-alkoxy-nor-β-lapachones and imidazole anthraquinones were synthesised and evaluated against bloodstream trypomastigote forms of the parasite. Compounds 2,2-dimethyl-3-(2,4-dibromophenylamino)-2,3-dihydro-naphtho[1,2-b]furan-4,5-dione, IC50/24 h 24.9 ± 7.4 and 4-azido-3-bromo-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione with 23.4 ± 3.8 μM showed a trypanosomicidal activity higher than benznidazole. These results demonstrate the potential of naphthoquinone derivatives as novel structures for the development of alternative drugs for Chagas' disease.
