One-Step Synthesis of 1H-1,2,3-Triazol-1-Ylmethyl-2,3-Dihydronaphtho[1,2-b]furan-4,5-Diones

被引：5
作者：
Chipoline, Ingrid C. [1 ]
Ferreira, Vitor F. [1 ]
da Silva, Fernando de C. [1 ]
机构：
[1] Univ Fed Fluminense, Inst Quim, Dept Quim Organ, BR-24020150 Niteroi, RJ, Brazil
来源：
CURRENT ORGANIC SYNTHESIS | 2015年 / 12卷 / 05期
关键词：
Quinones; nor-Lapachones; 1,2,3-triazoles; one-pot reactions; TRYPANOSOMA-CRUZI ACTIVITY; BETA-LAPACHONE; 1,2,3-TRIAZOLE DERIVATIVES; INHIBITORY-ACTIVITY; ANTITUMOR-ACTIVITY; NAPHTHOQUINONES; ANTIBACTERIAL; CYTOTOXICITY; ANTIPLATELET; ANTIFUNGAL;
D O I：
10.2174/157017941205150821125159
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report herein a straightforward and efficient route to prepare 1H-1,2,3-triazoles-linked to 2,3-dihydronaphtho[1,2-b]furan-4,5-dione in C-2 in a one-step reaction from readily available starting materials. We performed a one-step procedure from iodocyclization of 3-allyl-lawsone followed by a nucleophilic substitution reaction of the iodized product, and finally the Huisgen 1,3-dipolar cycloaddition reaction catalyzed by Cu(I) provide 1H-1,2,3-triazol-1-ylmethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-diones.
引用
收藏
页码：565 / 569
页数：5
相关论文
共 54 条
  • [1] MUTAGENICITY AND CARCINOGENICITY OF TOPOISOMERASE-INTERACTIVE AGENTS
    ANDERSON, RD
    BERGER, NA
    [J]. MUTATION RESEARCH-FUNDAMENTAL AND MOLECULAR MECHANISMS OF MUTAGENESIS, 1994, 309 (01) : 109 - 142
  • [2] 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
  • [3] BIAGI G, 1990, FARMACO, V45, P1181
  • [4] Novel 1,2,3-Triazole Derivatives for Use against Mycobacterium tuberculosis H37Rv (ATCC 27294) Strain
    Boechat, Nubia
    Ferreira, Vitor F.
    Ferreira, Sabrina B.
    Ferreira, Maria de Lourdes G.
    da Silva, Fernando de C.
    Bastos, Monica M.
    Costa, Marilia dos S.
    Lourenco, Maria Cristina S.
    Pinto, Angelo C.
    Krettli, Antoniana U.
    Aguiar, Anna Caroline
    Teixeira, Brunno M.
    da Silva, Nathalia V.
    Martins, Priscila R. C.
    Bezerra, Flavio Augusto F. M.
    Camilo, Ane Louise S.
    da Silva, Gerson P.
    Costa, Carolina C. P.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (17) : 5988 - 5999
  • [5] BOOTHMAN DA, 1989, CANCER RES, V49, P605
  • [6] Trypanosoma cruzi: in vitro activity of Epoxy-α-Lap, a derivative of α-lapachone, on trypomastigote and amastigote forms
    Bourguignon, S. C.
    Castro, H. C.
    Santos, D. O.
    Alves, C. R.
    Ferreira, V. F.
    Gama, I. L.
    Silva, F. C.
    Seguins, W. S.
    Pinho, R. T.
    [J]. EXPERIMENTAL PARASITOLOGY, 2009, 122 (02) : 91 - 96
  • [7] Trypanosoma cruzi: Insights into naphthoquinone effects on growth and proteinase activity
    Bourguignon, Saulo C.
    Cavalcanti, Danielle F. B.
    de Souza, Alessandra M. T.
    Castro, Helena C.
    Rodrigues, Carlos R.
    Albuquerque, Magaly G.
    Santos, Dilvani O.
    da Silva, Gabriel Gomes
    da Silva, Fernando C.
    Ferreira, Vitor F.
    de Pinho, Rosa T.
    Alves, Carlos R.
    [J]. EXPERIMENTAL PARASITOLOGY, 2011, 127 (01) : 160 - 166
  • [8] A New Approach for the Synthesis of 3-Substituted Cytotoxic Nor-β-Lapachones
    Cardoso, Mariana F. C.
    da Silva, Illana M. C. B.
    dos Santos Junior, Helvecio M.
    Rocha, David R.
    Araujo, Ana Jersia
    Pessoa, Claudia
    de Moraes, Manoel O.
    Lotufo, Leticia V. C.
    da Silva, Fernando de C.
    Santos, Wilson C.
    Ferreira, Vitor F.
    [J]. JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2013, 24 (01) : 12 - U321
  • [9] Potent Antileukemic Action of Naphthoquinoidal Compounds: Evidence for an Intrinsic Death Mechanism based on Oxidative Stress and Inhibition of DNA Repair
    Cavalcanti, Bruno C.
    Cabral, Igor O.
    Rodrigues, Felipe A. R.
    Barros, Francisco W. A.
    Rocha, Danilo D.
    Magalhaes, Hemerson I. F.
    Moura, Dinara J.
    Saffi, Jenifer
    Henriques, Joao A. P.
    Carvalho, Tatiane S. C.
    Moraes, Manoel O.
    Pessoa, Claudia
    de Melo, Isadora M. M.
    da Silva Junior, Eufranio N.
    [J]. JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2013, 24 (01) : 145 - U275
  • [10] Preclinical Genotoxicology of Nor-β-lapachone in Human Cultured Lymphocytes and Chinese Hamster Lung Fibroblasts
    Cavalcanti, Bruno C.
    Barros, Francisco W. A.
    Cabral, Igor O.
    Ferreira, Jose R.
    Magalhaes, Hemerson I. F.
    Junior, Helio V. N.
    da Silva Junior, Eufranio N.
    de Abreu, Fabiane C.
    Costa, Cicero O.
    Goulart, Marilia O. F.
    Moraes, Manoel O.
    Pessoa, Claudia
    [J]. CHEMICAL RESEARCH IN TOXICOLOGY, 2011, 24 (09) : 1560 - 1574
123456