Copper-catalyzed three-component synthesis of aminonaphthoquinone-sulfonylamidine conjugates and in vitro evaluation of their antiproliferative activity

被引：45
作者：
Suja, Thachapully D. [1 ]
Divya, K. V. L. [1 ]
Naik, Lakshma V. [1 ]
Kumar, A. Ravi [1 ,2 ]
Kamal, Ahmed [1 ,2 ]
机构：
[1] Indian Inst Chem Technol, CSIR, Med Chem & Pharmacol Div, Hyderabad 500007, Andhra Pradesh, India
[2] Natl Inst Pharmaceut Educ & Res, Dept Med Chem, Hyderabad 500037, Andhra Pradesh, India
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2016年 / 26卷 / 08期
关键词：
Aminonaphthoquinone; Sulfonylamidine; Topoisomerase inhibitor; Copper; Multicomponent reactions; MULTICOMPONENT REACTIONS; ANTICANCER ACTIVITY; ANTITUMOR-ACTIVITY; DERIVATIVES; CHEMISTRY; QUINONES; DESIGN; CANCER; 1,4-NAPHTHOQUINONES; CONSTRUCTION;
D O I：
10.1016/j.bmcl.2016.02.071
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A series of aminonaphthoquinone-sulfonylamidine conjugates were synthesized via a copper-catalyzed three-component reaction of N-propargyl aminonaphthoquinone, sulfonyl azides and various amines. Majority of the compounds exhibited promising antiproliferative potential when evaluated against a panel of four cancer cell lines. Docking experiments of representative compounds indicated that the conjugates can occupy the ATP-binding pocket of topoisomerase-II enzyme. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2072 / 2076
页数：5
相关论文
共 36 条
  • [1] Antitumor effects of two novel naturally occurring terpene quinones isolated from the Mediterranean ascidian Aplidium conicum
    Aiello, A
    Fattorusso, E
    Luciano, P
    Macho, A
    Menna, M
    Muñoz, E
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (09) : 3410 - 3416
  • [2] [Anonymous], 2011, OPEN GLYCOSCIENCE, DOI DOI 10.2174/1875398101104010001
  • [3] Antitumour quinones
    Asche, C
    [J]. MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2005, 5 (05) : 449 - 467
  • [4] Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine
    Bae, I
    Han, H
    Chang, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) : 2038 - 2039
  • [5] Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents
    Benites, Julio
    Valderrama, Jaime A.
    Bettega, Karina
    Pedrosa, Rozangela Curi
    Buc Calderon, Pedro
    Verrax, Julien
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (12) : 6052 - 6057
  • [6] Parallel synthesis and cytotoxicity evaluation of a polyamine-quinone conjugates library
    Bolognesi, Maria Laura
    Calonghi, Natalia
    Mangano, Chiara
    Masotti, Lanfranco
    Melchiorre, Carlo
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (17) : 5463 - 5467
  • [7] Sulfonamides and Sulfonylated Derivatives as Anticancer Agents
    Casini, Angela
    Scozzafava, Andrea
    Mastrolorenzo, Antonio
    Supuran, Claudiu T.
    [J]. CURRENT CANCER DRUG TARGETS, 2002, 2 (01) : 55 - 75
  • [8] Beyond Topoisomerase Inhibition: Antitumor 1,4-Naphthoquinones as Potential Inhibitors of Human Monoamine Oxidase
    Coelho-Cerqueira, Eduardo
    Netz, Paulo A.
    do Canto, Vanessa P.
    Pinto, Angelo C.
    Follmer, Cristian
    [J]. CHEMICAL BIOLOGY & DRUG DESIGN, 2014, 83 (04) : 401 - 410
  • [9] 1,2,3-Triazole-, arylamino- and thio-substituted 1,4-naphthoquinones: Potent antitumor activity, electrochemical aspects, and bioisosteric replacement of C-ring-modified lapachones
    da Cruz, Eduardo H. G.
    Hussene, Caio M. B.
    Dias, Gleiston G.
    Diogo, Emilay B. T.
    de Melo, Isadora M. M.
    Rodrigues, Bernardo L.
    da Silva, Mauro G.
    Valenca, Wagner O.
    Camara, Celso A.
    de Oliveira, Ronaldo N.
    de Paiva, Yen G.
    Goulart, Marilia O. F.
    Cavalcanti, Bruno C.
    Pessoa, Claudia
    da Silva Junior, Eufranio N.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (05) : 1608 - 1619
  • [10] Chemistry and Biology Of Multicomponent Reactions
    Domling, Alexander
    Wang, Wei
    Wang, Kan
    [J]. CHEMICAL REVIEWS, 2012, 112 (06) : 3083 - 3135
1234