New 1,4-di-N-oxide-quinoxaline-2-ylmethylene isonicotinic acid hydrazide derivatives as anti-Mycobacterium tuberculosis agents

被引:74
|
作者
Torres, Enrique [1 ]
Moreno, Elsa [1 ]
Ancizu, Saioa [1 ]
Barea, Carlos [1 ]
Galiano, Silvia [1 ]
Aldana, Ignacio [1 ]
Monge, Antonio [1 ]
Perez-Silanes, Silvia [1 ]
机构
[1] Univ Navarra, Unidad Invest & Desarrollo Medicamentos, CIFA, Pamplona 31008, Spain
关键词
Anti-tuberculosis agents; Quinoxaline 1,4-di-N-oxide derivatives; Isoniazid; Microwave assisted synthesis; Druglikeness; QUINOXALINE 1,4-DI-N-OXIDE DERIVATIVES; IN-VITRO EVALUATION; ANTIMYCOBACTERIAL ACTIVITY; DESIGN; QUINOXALINE-2-CARBONITRILE; HYDRAZONES; SAR;
D O I
10.1016/j.bmcl.2011.04.072
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The increase in the prevalence of drug-resistant tuberculosis cases demonstrates the need of discovering new and promising compounds with antimycobacterial activity. As a continuation of our research and with the aim of identifying new antitubercular drugs candidates, a new series of quinoxaline 1,4-di-N-oxide derivatives containing isoniazid was synthesized and evaluated for in vitro anti-tuberculosis activity against Mycobacterium tuberculosis H37Rv strain. Moreover, various drug-like properties of new compounds were predicted. Taking into account the biological results and the promising drug-likeness profile of these compounds, make them valid leads for further experimental research. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3699 / 3703
页数:5
相关论文
共 50 条
  • [31] Synthesis and Biological Evaluation of 3-Aryl-quinoxaline-2-carbonitrile 1,4-Di-N-oxide Derivatives as Hypoxic Selective Anti-tumor Agents
    Hu, Yunzhen
    Xia, Qing
    Shihao Shangguan
    Liu, Xiaowen
    Hu, Yongzhou
    Sheng, Rong
    MOLECULES, 2012, 17 (08): : 9683 - 9696
  • [32] New quinoxalinecarbonitrile 1,4-di-N-oxide derivatives as hypoxic-cytotoxic agents
    Ortega, MA
    Morancho, MJ
    Martínez-Crespo, FJ
    Sainz, Y
    Montoya, ME
    de Ceráin, AL
    Monge, A
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2000, 35 (01) : 21 - 30
  • [33] New quinoxaline 1,4-di-N-oxides.: Part 1:: Hypoxia-selective cytotoxins and anticancer agents derived from quinoxaline 1,4-di-N-oxides
    Amin, Kamelia M.
    Ismail, Magda M. F.
    Noaman, Eman
    Soliman, Dalia H.
    Ammar, Yousry A.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (20) : 6917 - 6923
  • [34] Synthesis and biological evaluation of 2,7-di-ester quinoxaline 1,4 di-N-oxide as antituberculosis agents
    Torres, Irma
    Sanchez-Sanchez, Mario
    Gomez-Caro, Lilia
    Bocanegra-Garcia, Virgilio
    Rivera, Gildardo
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [35] Anti-Trypanosoma cruzi and anti-leishmanial activity by quinoxaline-7-carboxylate 1,4-di-N-oxide derivatives
    Carlos Villalobos-Rocha, Juan
    Sanchez-Torres, Luvia
    Nogueda-Torres, Benjamin
    Segura-Cabrera, Aldo
    Garcia-Perez, Carlos A.
    Bocanegra-Garcia, Virgilio
    Palos, Isidro
    Monge, Antonio
    Rivera, Gildardo
    PARASITOLOGY RESEARCH, 2014, 113 (06) : 2027 - 2035
  • [36] Anti-Trypanosoma cruzi and anti-leishmanial activity by quinoxaline-7-carboxylate 1,4-di-N-oxide derivatives
    Juan Carlos Villalobos-Rocha
    Luvia Sánchez-Torres
    Benjamín Nogueda-Torres
    Aldo Segura-Cabrera
    Carlos A. García-Pérez
    Virgilio Bocanegra-García
    Isidro Palos
    Antonio Monge
    Gildardo Rivera
    Parasitology Research, 2014, 113 : 2027 - 2035
  • [37] QSAR analysis for quinoxaline-2-carboxylate 1,4-di-N-oxides as anti-mycobacterial agents
    Vicente, Esther
    Duchowicz, Pablo R.
    Castro, Eduardo A.
    Monge, Antonio
    JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2009, 28 (01): : 28 - 36
  • [38] Synthesis, 3D-QSAR analysis and biological evaluation of quinoxaline 1,4-di-N-oxide derivatives as antituberculosis agents
    Pan, Yuanhu
    Li, Panpan
    Xie, Shuyu
    Tao, Yanfei
    Chen, Dongmei
    Dai, Menghong
    Hao, Haihong
    Huang, Lingli
    Wang, Yulian
    Wang, Liye
    Liu, Zhenli
    Yuan, Zonghui
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (16) : 4146 - 4153
  • [39] Expanding the chemical space of ester of quinoxaline-7-carboxylate 1,4-di-N-oxide derivatives as potential antitubercular agents
    Gonzalez-Gonzalez, Alonzo
    Sanchez-Sanchez, Oscar
    Wan, Baojie
    Franzblau, Scott
    Palos, Isidro
    Espinoza-Hicks, Jose C.
    Moreno-Rodriguez, Adriana
    Martinez-Vazquez, Ana Veronica
    Lara-Ramirez, Edgar E.
    Ortiz-Perez, Eyra
    Paz-Gonzalez, Alma D.
    Rivera, Gildardo
    RSC MEDICINAL CHEMISTRY, 2024, 15 (08): : 2785 - 2791
  • [40] Trypanocidal Activity of Quinoxaline 1,4 Di-N-oxide Derivatives as Trypanothione Reductase Inhibitors
    Fabiola Chacon-Vargas, Karla
    Nogueda-Torres, Benjamin
    Sanchez-Torres, Luvia E.
    Suarez-Contreras, Erick
    Carlos Villalobos-Rocha, Juan
    Torres-Martinez, Yuridia
    Lara-Ramirez, Edgar E.
    Fiorani, Giulia
    Krauth-Siegel, R. Luise
    Bolognesi, Maria Laura
    Monge, Antonio
    Rivera, Gildardo
    MOLECULES, 2017, 22 (02):