- Synthesis and antiproliferative activity of quinolone nucleosides against the human myelogenous leukemia K-562 cell line
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A set of 6-substituted quinolone nucleosides linked to aniline or phenol via N or O heteroatom-bridges presenting new compounds were synthesized by palladium-catalyzed Buchwald-Hartwig cross-coupling reactions. 6-Bromoquinolone nucleoside precursors, bein
- Wicke, Lena,Engels, Joachim W.,Gambari, Roberto,Saab, Antoine M.
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- Synthesis of new porphyrin/4-quinolone conjugates and evaluation of their efficiency in the photoinactivation of Staphylococcus aureus
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Simple methodologies giving access to a new series of pophyrin/4-quinolone conjugates 6 and to the corresponding intra-cyclized derivatives 8 are described. The key steps to obtain 6 involved palladium-catalyzed amination reactions of 6-bromo-4-quinolones containing N-ethyl, N-pentyl and N-ribofuransyl substituents with (2-amino-5,10,15,20-tetraphenylporphyrinato)nickel(ii) followed by demetallation. Compounds 8 were obtained from compounds 4, the nickel(ii) complexes of 6, by an oxidative intracylization approach. The new conjugates were fully characterized and the evaluation of singlet oxygen production showed that these compounds possess good to high capability to generate singlet oxygen. The efficacy of these derivatives to photoinactivate Staphylococcus aureus, a Gram-positive bacteria, was evaluated and the best results were obtained with the N-ethyl derivatives 8a and 6a.
- Batalha, Pedro N.,Gomes, Ana T. P. C.,Forezi, Luana S. M.,Costa, Liliana,De Souza, Maria Cecília B. V.,Boechat, Fernanda Da C. S.,Ferreira, Vitor F.,Almeida, Adelaide,Faustino, Maria A. F.,Neves, Maria G. P. M. S.,Cavaleiro, José A. S.
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p. 71228 - 71239
(2015/09/08)
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- Molecular design, synthesis and biological evaluation of 1,4-dihydro-4-oxoquinoline ribonucleosides as TcGAPDH inhibitors with trypanocidal activity
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The 1,4-dihydro-4-oxoquinoline ribonucleoside, Neq135, is the first low micromolar trypanosomatidae inhibitor to show good ligand efficiency (0.28 kcal mol-1 atom-1) and good ligand lipophilicity efficiency (0.37 kcal mol-1/sup
- Soares, Fabyana A.,Sesti-Costa, Renata,Da Silva, Jo?o Santana,De Souza, Maria Cecília B.V.,Ferreira, Vitor F.,Da C. Santos, Fernanda,Monteiro, Patricia A.U.,Leit?o, Andrei,Montanari, Carlos A.
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supporting information
p. 4597 - 4601
(2013/08/15)
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- Synthesis and characterization of new porphyrin/4-quinolone conjugates
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New porphyrin/4-quinolone conjugates were synthesized from the Suzuki-Miyaura coupling reaction of a β-borylated porphyrin with bromo-4-quinolones containing N-ethyl and N-d-ribofuranosyl substituents. The use of electrospray ionization tandem mass spectrometry showed important information about the fragmentation pathways of the new compounds. It was possible to distinguish between those compounds with the porphyrin moiety linked at the 6-position of the quinolone unit from their 7-substituted isomers. The new compounds showed to be good singlet oxygen generators.
- Gomes, Ana T.P.C.,Cunha, Anna C.,Domingues, Maria Do Rosário M.,Neves, Maria G.P.M.S.,Tomé, Augusto C.,Silva, Artur M.S.,Santos, Fernanda Da C.,Souza, Maria C.B.V.,Ferreira, Vitor F.,Cavaleiro, José A.S.
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scheme or table
p. 7336 - 7342
(2011/10/09)
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