105438-12-8Relevant articles and documents
New strategies for the synthesis of naphthoquinones employing Cu(II) complexes: Crystal structures and cytotoxicity
Azeredo, Nathália F.B.,Souza, Fabrícia P.,Demidoff, Felipe C.,Netto, Chaquip D.,Resende, Jackson A.L.C.,Franco, Roberto W.A.,Colepicolo, Pio,Ferreira, Ana M.C.,Fernandes, Christiane
, p. 11 - 20 (2018)
The syntheses, physico-chemical characterization and cytotoxicity toward three human cell lines (standard and resistant sarcoma cells, and fibroblast) of a new copper(II) complex [Cu(HBPA)(L1)Cl]·3H2O 2 are reported. Complex 2 was obtained through the reaction between the ligand stilbene-quinone (HL1) and Cu[HBPA]Cl2 1, where HBPA = 2-hydroxybenzyl-2pyridylmethylamine. The synthesis of HL1 was performed in high yield through Heck reaction on PEG-400. X-ray diffraction and solution studies (UV–Vis, EPR, ESI(+)?MS and ESI(+)?MS/MS) were performed for complex 2, in which the copper(II) center is coordinated to the quinone in its deprotonated form, to the ligand HBPA and to a chloro ligand. Similar reaction employing CuCl2·2H2O, instead of Cu[HBPA]Cl2 1 and HL1, has resulted in the obtainment of a furano-o-naphtoquinone (L2) with 99% selectivity, suggesting a new methodology to cyclize the ligand HL1. In order to obtain the analogous para-isomer (L3), and to evaluate the isomerism influence on cytotoxicity activity, a cyclization reaction of HL1 with NBS (N-bromosuccinimide) was also performed, which resulted in the obtainment of L2 (8%) and L3 (13%). X-ray diffraction studies were performed for L2 and complex 2, and the description of their structure elucidated. Results from MTT assay revealed that complex 2 is more active against sarcoma cell lines (MES-SA/Dx5 and MES-SA) than both the free ligand HL1 and complex 1, reducing cell viability to less than 50 μmol L?1. L2 was the most active in the series, presenting cytotoxicity against resistant MES-SA/Dx5 and its standard MES-SA cell line, respectively, three and ten times higher than the current drug doxorubicin.
Growth inhibitory activity for cancer cell lines of lapachol and its natural and semi-synthetic derivatives
Fiorito, Serena,Epifano, Francesco,Bruyere, Celine,Mathieu, Veronique,Kiss, Robert,Genovese, Salvatore
, p. 454 - 457 (2014)
A series of 17 selected natural and semisynthetic 1,4-naphthoquinones were synthesized, and their growth inhibitory activity was evaluated in vitro. The compounds were tested on six human cancer cell lines using the MTT colorimetric assay. The data revealed that of the chemicals under study only lapachol, its acetate and 3-geranyllawsone displayed the highest activity, recording mean IC50 values ranging from 15 to 22 μM.
Synthesis and cytotoxicity evaluation of a series of 3-alkenyl-2-hydroxy-1,4-naphthoquinones obtained by an efficient knoevenagel condensation
David, Cibelle C.,Lins, Antonio C.S.,Silva, Tania M.S.,Campos, Júlia F.,Silva, Teresinha G.,Milit?o, Gardenia C.G.,Camara, Celso A.
, p. 8 - 18 (2019)
A modified and efficient Knoevenagel condensation procedure was developed to synthesize the title compounds using β-alanine and acetic acid as catalysts, showing good to excellent yields. We used lawsone with suitable aliphatic aldehydes including isobuty
A Complete and Unambiguous 1H and 13C NMR Signals Assignment of para?Naphthoquinones, ortho- And para-Furanonaphthoquinones
Borgati, Tatiane F.,de Souza Filho, José D.,de Oliveira, Alaíde B.
, p. 1138 - 1149 (2019/08/26)
A complete and unambiguous assignment of 1H and 13C nuclear magnetic resonance (NMR) signals of 29 naphthoquinones is reported on the basis of one- and two-dimensional NMR techniques (1H, 13C, 1H-sup
Synthesis of Stilbene-Quinone Hybrids through Heck Reactions in PEG-400
Demidoff, Felipe C.,De Souza, Fabrícia P.,Netto, Chaquip D.
, p. 5217 - 5223 (2017/11/28)
Styrenes were coupled with 3-iodolawsone in PEG-400 at 90 °C, leading stereoselectively to (E)-stilbene-quinone hybrids through Heck reactions. The best reaction conditions were found to be the use of NaOH (3 equiv) and 10 mol% of palladium acetate at 90 °C for 15 minutes. The chemical yields of the Heck reactions using styrenes with electron-withdrawing groups (65-98%) were greater than styrenes bearing electron-donating groups (7-32%) on the aromatic ring. In particular, the chemical yields of Heck reactions involving nitrostyrenes were the best ones observed.
Palladium(II)-catalyzed hydroxy-involved enolate-type efficient C-C functionalization of hydroxynaphthoquinones at room temperature
Wang, Nan,Wu, Xingsen,Qin, Taoyu,Zhou, Jianrui,You, Qidong,Zhang, Xiaojin
, p. 104126 - 104130 (2016/11/17)
A simple, mild, efficient (46-92%) and scalable strategy for the synthesis of hydroxynaphthoquinones was developed through a Pd-catalyzed hydroxy-involved enolate-type C-C bond formation reaction at room temperature. The functional group tolerance exhibited by this reaction, along with the possibility of scalable production, make it a method of choice for synthesizing diverse hydroxynaphthoquinones.
Styryl and functionalized aryl derivatives of lawsone through metal-free cross-coupling of its BF3-activated phenyliodonium ylide with cinnamaldehydes and arylaldehydes
Malamidou-Xenikaki, Elizabeth,Tsanakopoulou, Maria,Chatzistefanou, Maria,Hadjipavlou-Litina, Dimitra
, p. 5650 - 5661 (2015/08/03)
Phenyliodonium ylide of lawsone activated with BF3?Et2O reacts with cinnamaldehydes to afford 2-hydroxy-3-styryl-1,4-naphthoquinones in good to excellent yields and relatively high level of stereospecificity through deformylation of the aldehydes. The product yield is diminished with a methoxy substituted cinnamaldehyde and becomes zero with a dimethoxy substituted substrate giving rise to another product, 2-hydroxy-3-aryl-1,4-naphthoquinone. The reaction of the same ylide with salicylic aldehydes forms 2-hydroxy-3-(2-hydroxyaryl)-1,4-naphthoquinones and/or benzo[d]naphtha[2,1-b]furano-5,6-diones, depending on the reaction conditions applied. Plausible reaction mechanisms explaining the formation of these products are proposed. The products showed potent antioxidant activity and inhibited lipoxygenase.
Functionalized hydroxyquinones through Suzuki-type coupling of phenyliodonium ylides of hydroxyquinones with arylboronic acids
Kazantzi, Georgia,Malamidou-Xenikaki, Elizabeth,Spyroudis, Spyros
, p. 2597 - 2600 (2008/09/16)
The palladium(II) acetate catalyzed reaction of phenyliodonium ylides of 2-hydroxyquinones with arylboronic acids affords a variety of 3-substituted 2-hydroxyquinone derivatives. Best yields are obtained by using tri(tert-butyl)phosphine as a ligand. Georg Thieme Verlag Stuttgart.
