Synthesis and antimicrobial activity of new 1,2,4-triazole-3-thiol metronidazole derivatives

被引:39
作者
Saadeh, Haythem A. [1 ]
Mosleh, Ibrahim M. [2 ]
Al-Bakri, Amal G. [3 ]
Mubarak, Mohammad S. [1 ]
机构
[1] Univ Jordan, Fac Sci, Dept Chem, Amman 11942, Jordan
[2] Univ Jordan, Fac Sci, Dept Biol Sci, Amman 11942, Jordan
[3] Univ Jordan, Fac Pharm, Dept Pharmaceut & Pharmaceut Technol, Amman 11942, Jordan
来源
MONATSHEFTE FUR CHEMIE | 2010年 / 141卷 / 04期
关键词
Triazoles; Metronidazole; Antiparasitic activity; Antimicrobial activity; ANTIBACTERIAL;
D O I
10.1007/s00706-010-0281-9
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
New 1,2,4-triazole-3-thiol metronidazole derivatives have been synthesized by treating 1,2,4-triazole-3-thiols with metronidazole tosylate (toluene-4-sulfonic acid 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester) in DMF and in the presence of potassium carbonate as a base. S-alkylated and N-alkylated products were obtained, with the S-alkylated being the major products. All of the newly synthesized compounds were characterized by IR, H-1 NMR, C-13 NMR, and high-resolution mass spectrometry. The antiparasitic activity of the compounds against Entamoeba histolytica and Giardia intestinalis was investigated. The antibacterial and antifungal activity of the compounds, assessed as minimal inhibitory concentration, was also investigated.
引用
收藏
页码:471 / 478
页数:8
相关论文
共 36 条
  • [1] Abu-Shaireh EAM, 2009, Eur Pat Appl EP, Patent No. [2985394 A2, 2985394]
  • [2] Al-Zghoul KH, 2005, HETEROCYCLES, V65, P2937
  • [3] Almajan GL, 2008, J ENZYM INHIB MED CH, V23, P101, DOI [10.1080/14756360701342417, 10.1080/14756360701342417 ]
  • [4] [Anonymous], CHEM ABSTR
  • [5] Synthesis and antibacterial activity evaluation of metronidazole-triazole conjugates
    Beena
    Kumar, Nitin
    Rohilla, Rajesh K.
    Roy, N.
    Rawat, Diwan S.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (05) : 1396 - 1398
  • [6] Synthesis and anti-Helicobacter pylori properties of NO-donor/metronidazole hybrids and related compounds
    Bertinaria, M
    Galli, U
    Sorba, G
    Fruttero, R
    Gasco, A
    Brenciaglia, MI
    Scaltrito, MM
    Dubini, F
    [J]. DRUG DEVELOPMENT RESEARCH, 2003, 60 (03) : 225 - 239
  • [7] Brucato A, 1978, Boll Soc Ital Biol Sper, V54, P1051
  • [8] Synthesis of some new 4,5-substituted-4H-1,2,4-triazole-3-thiol derivatives
    Cansiz, A
    Koparir, M
    Demirdag, A
    [J]. MOLECULES, 2004, 9 (04) : 204 - 212
  • [9] N-vinyl-nitroimidazole cycloadditions:: Potential routes to nucleoside analogues
    Clayton, R
    Ramsden, CA
    [J]. SYNTHESIS-STUTTGART, 2005, (16): : 2695 - 2700
  • [10] Coffen D. L., 1974, US Pat, Patent No. [3 849 434, 3849434]