Fluorinated 1,2,4-Triazolo[1,5-a]pyrimidine-6-carboxylic Acid Derivatives as Antimycobacterial Agents

被引：32
|
作者：
Abdel-Rahman, Hamdy M. [1 ]
El-Koussi, Nawal A. [1 ]
Hassan, Hoda Y. [1 ]
机构：
[1] Assiut Univ, Fac Pharm, Dept Med Chem, Assiut 71526, Egypt
来源：
ARCHIV DER PHARMAZIE | 2009年 / 342卷 / 02期
关键词：
Antimycobacterial activity; Fluoroquinolone analogues; Mycobacterium tuberculosis; 1,2,4-Triazolo[1,5-a]pyrimidines; POTENTIAL ANTIMICROBIAL AGENTS; ANTIBACTERIAL ACTIVITY; MYCOBACTERIUM-TUBERCULOSIS; QUINOLONE ANTIBACTERIALS; ANALOGS;
D O I：
10.1002/ardp.200800113
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A series of fluorinated 1,2,4-triazolo[1,5-a]pyrimidine-6-carboxylic acid derivatives was designed and synthesized as fluoroquinolone analogues. The synthesized compounds were screened against Mycobacterium tuberculosis H(37)R(v) strain at 6.25 mu g/mL concentration. Compound 4, the 7-oxo-2-(trifluoromethyl)-4,7-dihydro-1,2,4-triazolo[5,1-a]pyrimidine-6-carboxylic acid was found to be a very potent inhibitor, being able to inhibit 92% growth of M. tuberculosis H(37)R(v) at 6.25 mu g/mL concentration. At the same time, it proofed to be nontoxic to mammalian cells (IC(50) > 62.5 mu g/mL in VERO cells).
引用
收藏
页码：94 / 99
页数：6
相关论文
共 50 条
  • [41] Synthesis and Biological Activity of Diheterocyclic 5,7-Dimethyl-1,2,4-triazolo[1,5-a]pyrimidine Derivatives
    Ma, Zhong-Hua
    Liu, Zu-Ming
    Chen, Qiong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (11) : 1965 - 1970
  • [42] Synthesis and evaluation of ursolic acid-based 1,2,4-triazolo[1,5-a]pyrimidines derivatives as anti-inflammatory agents
    Tian-Yi Zhang
    Chun-Shi Li
    Ping Li
    Xue-Qian Bai
    Shu-Ying Guo
    Ying Jin
    Sheng-Jun Piao
    Molecular Diversity, 2022, 26 : 27 - 38
  • [43] Corrosion Inhibition of Mild Steel in Acidic Solutions Using 1,2,4-Triazolo[1,5-a]pyrimidine
    I. R. Saad
    A. M. Abdel-Gaber
    G. O. Younes
    B. Nsouli
    Russian Journal of Applied Chemistry, 2018, 91 : 245 - 252
  • [44] Corrosion Inhibition of Mild Steel in Acidic Solutions Using 1,2,4-Triazolo[1,5-a]pyrimidine
    Saad, I. R.
    Abdel-Gaber, A. M.
    Younes, G. O.
    Nsouli, B.
    RUSSIAN JOURNAL OF APPLIED CHEMISTRY, 2018, 91 (02) : 245 - 252
  • [45] Synthesis and evaluation of ursolic acid-based 1,2,4-triazolo[1,5-a]pyrimidines derivatives as anti-inflammatory agents
    Zhang, Tian-Yi
    Li, Chun-Shi
    Li, Ping
    Bai, Xue-Qian
    Guo, Shu-Ying
    Jin, Ying
    Piao, Sheng-Jun
    MOLECULAR DIVERSITY, 2022, 26 (01) : 27 - 38
  • [46] The crystal and molecular structures of dichlorobis(5,7-diphenyl-1,2,4-triazolo[1,5-a ] pyrimidine)zinc(II) (1) and dichlorobis(5,7-diphenyl-1,2,4-triazolo[1,5-a ] pyrimidine)cobalt(II) (2)
    Inorganica Chimica Acta, 260 (02):
  • [47] USE OF FORMAMIDE IN SYNTHESIS OF 1,2,4-TRIAZOLO[1,5-A]BENZIMIDAZOLES
    KUZMENKO, VV
    KUZMENKO, TA
    SIMONOV, AM
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1987, (02): : 278 - 278
  • [48] 6-nitro-derivatives and 6-bromo-derivatives of 7-hydroxo-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine
    Kofman, TP
    Uvarova, TA
    Kartseva, GY
    Uspenskaya, TL
    ZHURNAL ORGANICHESKOI KHIMII, 1997, 33 (12): : 1867 - 1876
  • [49] Synthesis and Antitumor Activity of 1,2,4-Triazolo[1,5-a]quinazolines
    Al-Salahi, R.
    Marzouk, M.
    Ashour, A. E.
    Alswaidan, I.
    ASIAN JOURNAL OF CHEMISTRY, 2014, 26 (07) : 2173 - 2176
  • [50] Synthesis, X-ray, spectroscopic characterization, DFT and antioxidant activity of 1,2,4-triazolo[1,5-a]pyrimidine derivatives
    Lahmidi, Sanae
    Anouar, El Hassane
    El Hafi, Mohamed
    Boulhaoua, Mohammed
    Ejjoummany, Abdelaziz
    El Jemli, Meryem
    Essassi, El Mokhtar
    Mague, Joel T.
    JOURNAL OF MOLECULAR STRUCTURE, 2019, 1177 : 131 - 142
12345