68963-21-3Relevant articles and documents
Synthesis, molecular docking, and biological activity of thioether derived from juglone in preclinical models of chronic myeloid leukemia
B. S. M. R. Gomes, Carinne,Cordeiro, Pamella S.,Daniel, Julio P.,E. A. de Moraes, Maria,Ferreira, Vitor F.,Montenegro, Raquel C.,Moreira, Caroline S.,Vasconcellos, Marne C.,da Rocha, David R.,da S. M. Forezi, Luana,de F. A. Moreira-Nunes, Caroline,de S. Portilho, Adrhyann J.,do Nascimento, Vanessa
, (2021/11/09)
In this work, 16 new thio-1,4-naphthoquinones were synthesized, and their antiproliferative effects against tumor cell lines SK-MEL-19, AGP-01, ACP-02, HL-60, K-562, K-562-Lucena-1, FEPS, and non-neoplastic human fibroblast MRC-5, were examined. The compounds were selective active against leukemia cell lines. Based on the screening results for cytotoxic activity, naphthoquinone 11a showed higher cytotoxicity on the chemoresistant leukemia (FEPS) cell line when compared to the chemosensitive (K-562) cell line. Moreover, naphthoquinone 11a presented excellent ADME/T and did not violate Lipinski's rule of five, indicating good oral absorption. Target prediction revealed DNA topoisomerase I (TOP1) as a possible target of 11a. The molecular docking prediction showed an ? 11.94 kcal/mol binding affinity interaction of 11a with TOP1, involving three hydrogen bonds to ARG364, A113, and G11 from the active site of the enzyme. In addition, naphthoquinone 11a significantly suppressed the expression of the TOP1 gene in K-562 and FEPS leukemia cell lines. The naphthoquinone 11a induced significant changes in cell morphology, demonstrating cell and nuclear shrinkage, blebbing formation as well and fragmentation of the cell into apoptotic bodies. Thus, 11a could be a drug that leads to a new set of TOP1 major inhibitors. In summary, the present study showed a cytotoxic effect of 11a against chemoresistant and chemosensitive leukemia cell lines with TOP1 as a possible target.
Synthesis of new 9-hydroxy-α- and 7-hydroxy-β-pyran naphthoquinones and cytotoxicity against cancer cell lines
Da Rocha, David R.,De Souza, Ana C. G.,Resende, Jackson A. L. C.,Santos, Wilson C.,Dos Santos, Evelyne A.,Pessoa, Claudia,De Moraes, Manoel O.,Costa-Lotufo, Leticia V.,Montenegro, Raquel C.,Ferreira, Vitor F.
experimental part, p. 4315 - 4322 (2011/07/08)
A synthetic method to obtain α- and β-pyran naphthoquinones 10 and 11 with a hydroxyl substituent on the aromatic ring was developed. Two series of α- and β-pyran naphthoquinones were obtained from the 8-hydroxy-lawsone, and their anticancer properties we
Synthesis and antifungal activity of 2/3-arylthio- and 2,3-bis(arylthio)-5- hydroxy-/5-methoxy-1,4-naphthoquinones
Ryu, Chung-Kyu,Shim, Ju-Yeon,Mi, Jin Chae,Ik, Hwa Choi,Han, Ja-Young,Jung, Ok-Jai,Jung, Yoon Lee,Seong, Hee Jeong
, p. 438 - 444 (2007/10/03)
2/3-Arylthio- and 2,3-bis(arylthio)-5-hydroxy-/5-methoxy-1,4- naphthoquinones 5-9 were synthesized and tested for in vitro antifungal activity against Candida species and Aspergillus niger. The synthesized compounds 5-9 generally showed good activities ag
