Combination of Aryl Diselenides/Hydrogen Peroxide and Carbon-Nanotube/Rhodium Nanohybrids for Naphthol Oxidation: An Efficient Route towards Trypanocidal Quinones

被引：25
作者：
de Carvalho, Renato L. [1 ]
Jardim, Guilherme A. M. [1 ]
Santos, Augusto C. C. [1 ]
Araujo, Maria H. [1 ]
Oliveira, Willian X. C. [1 ]
Bombaca, Ana Cristina S. [2 ]
Menna-Barreto, Rubem F. S. [2 ]
Gopi, Elumalai [3 ]
Gravel, Edmond [3 ]
Doris, Eric [3 ]
da Silva Junior, Eufranio N. [1 ]
机构：
[1] Univ Fed Minas Gerais, Dept Chem, Inst Exact Sci, BR-31270901 Belo Horizonte, MG, Brazil
[2] Fiocruz MS, Inst Oswaldo Cruz, BR-21045900 Rio De Janeiro, RJ, Brazil
[3] Univ Paris Saclay, CEA, SCBM, F-91191 Gif Sur Yvette, France
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 57期
关键词：
carbon nanotubes; Chagas disease; oxidation; quinones; rhodium nanohybrid; selenium; HYDROGEN-PEROXIDE; BENZENESELENINIC ACID; CATALYTIC-OXIDATION; BETA-LAPACHONE; CANCER-CELLS; PHENOLS; HYDROQUINONE; DERIVATIVES; CYCLOADDITION; ANHYDRIDE;
D O I：
10.1002/chem.201802773
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
This work reports a combination of aryl diselenides/hydrogen peroxide and carbon-nanotube (CNT)/rhodium nanohybrids (RhCNT) for naphthol oxidation towards the synthesis of 1,4-naphthoquinones and evaluation of their relevant trypanocidal activity. Under a combination of (PhSe)(2)/H2O2 in the presence of O-2 in iPrOH/hexane, several benzenoid (A-ring)-substituted quinones were prepared in moderate to high yields. We also studied the contribution of RhCNT as co-catalyst in this process and, in some cases, yields were improved. This method provides an efficient and versatile alternative for preparing A-ring-modified naphthoquinonoid compounds with relevant biological profile.
引用
收藏
页码：15227 / 15235
页数：9
相关论文
共 74 条
  • [1] [Anonymous], 2004, PERS VIS RAYTR
  • [2] [Anonymous], 2015, CrysAlisPro software system
  • [3] Molecular hybridization as a powerful tool towards multitarget quinoidal systems: synthesis, trypanocidal and antitumor activities of naphthoquinone-based 5-iodo-1,4-disubstituted-, 1,4-and 1,5-disubstituted-1,2,3-triazoles
    Bahia, Samara Ben B. B.
    Reis, Wallace J.
    Jardim, Guilherme A. M.
    Souto, Francielly T.
    de Simone, Carlos A.
    Gatto, Claudia C.
    Menna-Barreto, Rubem F. S.
    de Castro, Solange L.
    Cavalcanti, Bruno C.
    Pessoa, Claudia
    Araujo, Maria H.
    da Silva Junior, Eufranio N.
    [J]. MEDCHEMCOMM, 2016, 7 (08) : 1555 - 1563
  • [4] OXIDATION OF PHENOLS TO QUINONES BY BIS(TRIFLUOROACETOXY)IODOBENZENE
    BARRET, R
    DAUDON, M
    [J]. TETRAHEDRON LETTERS, 1990, 31 (34) : 4871 - 4872
  • [5] EXPERIMENTS ON SYNTHESIS OF TETRACYCLINE .15. OXIDATION OF PHENOLS AND RING-A MODEL PHENOLS TO O-HYDROXY-DIENONES WITH BENZENE-SELENINIC ANHYDRIDE
    BARTON, DHR
    LEY, SV
    MAGNUS, PD
    ROSENFELD, MN
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (05): : 567 - 572
  • [6] COMPARATIVE OXIDATION OF PHENOLS WITH BENZENESELENINIC ANHYDRIDE AND WITH BENZENESELENINIC ACID
    BARTON, DHR
    FINET, JP
    THOMAS, M
    [J]. TETRAHEDRON, 1988, 44 (20) : 6397 - 6406
  • [7] An NQO1-and PARP-1-mediated cell death pathway induced in non-small-cell lung cancer cells by β-lapachone
    Bey, Erik A.
    Bentle, Melissa S.
    Reinicke, Kathryn E.
    Dong, Ying
    Yang, Chin-Rang
    Girard, Luc
    Minna, John D.
    Bornmann, William G.
    Gao, Jinming
    Boothman, David A.
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (28) : 11832 - 11837
  • [8] Mornings with art, lessons learned: Feedback regulation, restriction threshold biology, and redundancy govern molecular stress responses
    Bey, Erik A.
    Wuerzberger-Davis, Shelly M.
    Pink, John J.
    Yang, Chin-Rang
    Araki, Shinako
    Reinicke, Kathryn E.
    Bentle, Melissa S.
    Doing, Ying
    Cataldo, Eva
    Criswell, Tracy L.
    Wagner, Mark W.
    Li, Longshan
    Gao, Jinming
    Boothman, David A.
    [J]. JOURNAL OF CELLULAR PHYSIOLOGY, 2006, 209 (03) : 604 - 610
  • [9] Pyranonaphthoquinone antibiotics - isolation, structure and biological activity
    Brimble, MA
    Duncalf, LJ
    Nairn, MR
    [J]. NATURAL PRODUCT REPORTS, 1999, 16 (03) : 267 - 281
  • [10] COMPOUNDS FROM DANSHEN .4. STRUCTURE ACTIVITY RELATIONSHIP OF MILTIRONE, AN ACTIVE CENTRAL BENZODIAZEPINE RECEPTOR LIGAND ISOLATED FROM SALVIA-MILTIORRHIZA BUNGE (DANSHEN)
    CHANG, HM
    CHUI, KY
    TAN, FWL
    YANG, Y
    ZHONG, ZP
    LEE, CM
    SHAM, HL
    WONG, HNC
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (05) : 1675 - 1692
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