62452-63-5Relevant academic research and scientific papers
Transition-Metal-Free One-Pot Synthesis of Naphthoquinonefuran Derivatives through Sequential Nucleophilic Substitution-Nucleophilic Addition Reaction
Li, Xiang,Sun, Peng,Xie, Kaijun,Zhou, Dun,Peng, Jinsong,Fan, Aihong,Zhang, Jing,Chen, Chunxia
, p. 9313 - 9320 (2020)
A transition-metal-free route for tandem one-pot synthesis of naphthoquinonefuran derivatives from 2-hydroxynaphthoquinones has been developed. The sequentially accomplished process comprises an intermolecular alkynylation of sp2-carbon at the 3 position of 2-hydroxynaphthoquinones with arylethynyl bromides, followed by a base-promoted intramolecular nucleophilic annulation reaction. A broad range of functional groups is compatible with this reaction, and diverse naphtho[2,3-b]furan-4,9-diones can be obtained with good yields and excellent regioselectivity.
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, anti-proliferative activity evaluation and 3D-QSAR study of naphthoquinone derivatives as potential anti-colorectal cancer agents
Acu?a, Julio,Piermattey, Jhoan,Caro, Daneiva,Bannwitz, Sven,Barrios, Luis,López, Jairo,Ocampo, Yanet,Vivas-Reyes, Ricardo,Aristizábal, Fabio,Gaitán, Ricardo,Müller, Klaus,Franco, Luis
, (2018/02/06)
Colorectal cancer (CRC) is a disease with high incidence and mortality, constituting the fourth most common cause of death from cancer worldwide. Naphthoquinones are attractive compounds due to their biological and structural properties. In this work, 36 naphthoquinone derivatives were synthesized and their activity evaluated against HT-29 cells. Overall, high to moderate anti-proliferative activity was observed in most members of the series, with 15 compounds classified as active (1.73 50 2 = 0.99 and q2 = 0.625). This model allowed proposing five new compounds with two-fold higher theoretical anti-proliferative activity, which would be worthwhile to synthesize and evaluate. Further investigations will be needed to determine the mechanism involved in the effect of most active compounds which are potential candidates for new anticancer agents.
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 (2017/09/26)
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.
Synthesis of Stilbene-Quinone Hybrids through Heck Reactions in PEG-400
Demidoff, Felipe C.,De Souza, Fabrícia P.,Netto, Chaquip D.
supporting information, 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.
Method for synthesizing coumarone naphthoquinone derivative
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Paragraph 0070; 0080; 0081; 0082, (2016/10/08)
The invention discloses a method for synthesizing a coumarone naphthoquinone derivative. The method comprises the following steps that 2-hydroxyl-3-substituted ethylene-1,4-naphthoquinone is used as raw materials, and the angular coumarone naphthoquinone derivative is synthesized in an organic solvent under the effect of iodine; or the 2-hydroxyl-3-substituted ethylene-1,4-naphthoquinone is used as raw materials, the angular coumarone naphthoquinone derivative is firstly synthesized in an organic solvent under the effect of the iodine, and then, the angular coumarone naphthoquinone derivative is used for synthesizing the straight coumarone naphthoquinone derivative under the acid condition. The method has the advantages that the experiment steps are few; the operation is simple; the selectivity is high; the yield is high; a higher application value is realized.
Base-Mediated Cyclization Reaction of 2-(5-Hydroxy-1-pentynyl)benzonitriles to 4-Amino-2,3-dihydronaphtho[2,3-b]furanes and Synthesis of Furanonaphthoquinones
Tsai, Chih-Jyun,Chen, Chin-Chau,Tsai, Chih-Wei,Wu, Ming-Jung
, p. 3882 - 3889 (2016/05/24)
An efficient transformation of 2-(5-hydroxy-1-pentynyl)benzonitriles 5 to furanonaphthoquinones 11 is presented. Treatment of 5 with 1.5 equiv of NaOMe in DMSO at 140 °C for 0.5 h gave 6 in good yields. Conversion of 6 to 11 was carried out by oxidation of 6 with Fremy's salt and KH2PO4 in acetone and water, followed by dehydrogenation using palladium on charcoal in diphenylether at reflux temperature.
The iodine-mediated highly regioselective synthesis of angular and linear naphthofuroquinones
Liu, Suyou,Long, Lijun,Xie, Duoduo,Liu, Lijun,Ma, Dayou
supporting information, p. 6730 - 6733 (2018/05/14)
Naphthofuroquinones are of great value in medicinal chemistry. In this letter, a facile method for highly regioselective synthesis of both linear and angular naphthofuroquinones has been developed via iodine mediated cyclization of 2-hydroxy-3-substituted
One-Step Synthesis of Naphthofurandione, Benzofurandione, and Phenalenofuranone Derivatives by the CAN-Mediated Cycloaddition
Kobayashi, Kazuhiro,Uneda, Tomokazu,Tanaka, Koujirou,Mori, Masako,Tanaka, Hideo,Morikawa, Osamu,Konishi, Hisatoshi
, p. 1691 - 1697 (2007/10/03)
The 3+2-type cycloaddition reaction of 2-hydroxy-1,4-naphthoquinones with various alkenes or phenylacetylene was mediated by ammonium cerium(IV) nitrate (CAN) to give the corresponding naphtho[2,3-b]furan-4,9-dione and naphtho[1,2-[furan-4,5-dione derivatives. The reaction of 2-hydroxy-1,4-benzoquinones with alkenes in the presence of CAN similarly proceeded to give benzofuran-4,7-dione and benzofuran-4,5-dione derivatives. 3-Hydroxy-1H-phenalen-1-one also underwent the CAN-mediated cycloaddition with alkenes or phenylacetylene to give the corresponding 7H-phenaleno[1,2-b]furan-7-one derivatives.
One-pot synthesis of naphtho[2,3-b]furan-4,9-diones by sequential coupling/ring closure reactions
Kobayashi, Kazuhiro,Uneda, Tomokazu,Kawakita, Masataka,Morikawa, Osamu,Konishi, Hisatoshi
, p. 837 - 840 (2007/10/03)
Treatment of 3-phenyliodonio-1,2,3,4-tetrahydronaphthalenides with terminal acetylenes in the presence of a bis(triphynylphosphine)palladium chloride-cuprous iodide catalyst or cuprous oxide in N-methylpiperidine or pyridine, respectively, furnished the corresponding 2-substituted naphtho[2,3-b]furan-4,9-diones in moderate to good yields. The utility of this method was demonstrated in the synthesis of a cytotoxic natural product, 2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione.
