Synthesis and antimycobacterial activity of new quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives

被引：102
|
作者：
Zarranz, B [1 ]
Jaso, A [1 ]
Aldana, I [1 ]
Monge, A [1 ]
机构：
[1] Univ Navarra, Unidad Invest & Desarrollo Medicamentos, Ctr Invest Farmacobiol Aplicada, E-31080 Pamplona, Spain
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2003年 / 11卷 / 10期
关键词：
D O I：
10.1016/S0968-0896(03)00119-6
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
As a continuation of our research and with the aim of obtaining new antituberculosis agents which can improve the current chemotherapeutic antituberculosis treatments, new series of quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives were synthesized and evaluated for in vitro antituberculosis activity against Mycobacterium tuberculosis strain H(37)Rv, using the radiometric BACTEC 460-TB methodology. Active compounds were also screened by serial dilution to assess toxicity to a VERO cell line. The results indicate that some compounds exhibited a good antituberculosis activity and the arylearboxamide analogues 3, 8, and 9 were the most active compounds (EC90/MICI). Also, the cytotoxic effects indicate that these compounds have a good Selectivity Index (SI). (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2149 / 2156
页数：8
相关论文
共 50 条
  • [41] Selective toxicity of a quinoxaline 1,4-di-N-oxide derivative in human tumour cell lines
    Azqueta, A
    Pachón, G
    Cascante, M
    Creppy, EE
    Monge, A
    de Cerain, AL
    ARZNEIMITTELFORSCHUNG-DRUG RESEARCH, 2005, 55 (03): : 177 - 182
  • [42] Synthesis and structure-activity relationship of 3-phenylquinoxaline 1,4-di-N-oxide derivatives as antimalarial agents
    Vicente, Esther
    Lima, Lidia M.
    Bongard, Emily
    Charnaud, Sarah
    Villar, Raquel
    Solano, Beatriz
    Burguete, Asuncion
    Perez-Silanes, Silvia
    Aldana, Ignacio
    Vivas, Livia
    Monge, Antonio
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (09) : 1903 - 1910
  • [43] 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
  • [44] Synthesis and in vitro evaluation of new ethyl and methyl quinoxaline-7-carboxylate 1,4-di-N-oxide against Entamoeba histolytica
    Estela Duque-Montano, Blanca
    Citlalli Gomez-Caro, Lilia
    Sanchez-Sanchez, Mario
    Monge, Antonio
    Hernandez-Baltazar, Efren
    Rivera, Gildardo
    Torres-Angeles, Oscar
    BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (15) : 4550 - 4558
  • [45] A Comparative Study of Conventional and Microwave-Assisted Synthesis of Quinoxaline 1,4-di-N-oxide N-acylhydrazones Derivatives Designed as Antitubercular Drug Candidates
    dos Santos Fernandes, Guilherme Felipe
    Moreno-Viguri, Elsa
    Santivanez-Veliz, Mery
    Paucar, Rocio
    Chin, Chung Man
    Perez-Silanes, Silvia
    dos Santos, Jean Leandro
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (04) : 2380 - 2388
  • [46] Improved Computational Prediction of the Electrochemical Reduction Potential of Twenty 3-Aryl-Quinoxaline-2-Carbonitrile 1,4-Di-N-Oxide Derivatives
    Bhattarai, Shambhu
    Mareta, Pradeep
    Crawford, Philip W.
    Kessler, Jonathan M.
    Ragain, Christina M.
    COMPUTATION, 2023, 11 (01)
  • [47] Voltammetric Study of Some 3-Aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide Derivatives with Anti-Tumor Activities
    Miller, Eric M.
    Xia, Qing
    Cella, Mariah E.
    Nenninger, Austin W.
    Mruzik, Monica N.
    Brillos-Monia, Krystina A.
    Hu, Yong Zhou
    Sheng, Rong
    Ragain, Christina M.
    Crawford, Philip W.
    MOLECULES, 2017, 22 (09)
  • [48] Photochemical and photobiological studies of tirapazamine (SR 4233) and related quinoxaline 1,4-di-N-oxide analogues
    Inbaraj, JJ
    Motten, AG
    Chignell, CF
    CHEMICAL RESEARCH IN TOXICOLOGY, 2003, 16 (02) : 164 - 170
  • [49] 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
  • [50] Antiplasmodial structure-activity relationship of 3-trifluoromethyl-2-arylcarbonylquinoxaline 1,4-di-N-oxide derivatives
    Marin, Adoracion
    Lima, Lidia Moreira
    Solano, Beatriz
    Vicente, Esther
    Silanes, Silvia Perez
    Maurel, Severine
    Sauvain, Michel
    Aldana, Ignacio
    Monge, Antonio
    Deharo, Eric
    EXPERIMENTAL PARASITOLOGY, 2008, 118 (01) : 25 - 31
12345