sodium O-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl carbonodithioate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: sodium O-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl carbonodithioate
• 英文别名: metronidazole xanthate sodium salt；Metronidazole xanthate；sodium;2-(2-methyl-5-nitroimidazol-1-yl)ethoxymethanedithioate
• 化学式: C₇H₈N₃O₃S₂*Na
• 分子量: 269.281
• InChiKey: CZMQLUJXVRAEOU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.05
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二硫化碳 、 甲硝唑 在 sodium hydroxide 作用下， 以 乙二醇二甲醚 为溶剂， 以30%的产率得到sodium O-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl carbonodithioate
  参考文献：
  名称：

  A novel [99mTcN]2+ complex of metronidazole xanthate as a potential agent for targeting hypoxia

  摘要：

  A xanthate derivative (L) at the pendant hydroxy group of metronidazole, a nitroimidazole known to possess affinity for hypoxic tumors, has been used as the carrier molecule for targeted delivery of the gamma-emitting radioisotope Tc-99m to tumors. The xanthate residues (S-2(-)) from two molecules of this ligand (L) were used for chelation with the [(TcN)-Tc-99m](2+) intermediate to form a square pyramidal and neutral [(TcN)-Tc-99m/L-2] complex in > 95% yield using a low ligand concentration of 1 mg/mL (similar to 3 x 10(-3) M). Biodistribution studies carried out in Swiss mice bearing fibrosarcoma tumor showed selective accumulation of the injected activity in the tumor (1.44 +/- 0.26% per gram 1 h pi) with major clearance through hepatobiliary route. The complex showed high tumor/muscle ratio (2.15 and 3.35 at 1 and 3 h post-injection, respectively) and tumor/blood ratio, which were comparable to hypoxia targeting agents Tc-99m-BMS181321 and Tc-99m-BRU59-21 reported earlier. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.030

文献信息

• Imidazole derivatives as possible microbicides with dual protection
  作者：Lalit Kumar、Amit Sarswat、Nand Lal、Vishnu L. Sharma、Ashish Jain、Rajeev Kumar、Vikas Verma、Jagdamba P. Maikhuri、Awanit Kumar、Praveen K. Shukla、Gopal Gupta

  DOI：10.1016/j.ejmech.2009.10.021

  日期：2010.2

  Twenty seven derivatives (2-28) of 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol were synthesized and evaluated for anti-trichomonas, spermicidal and antifungal activities. Twenty six compounds were active against Trichomonas vaginalis at MIC ranging from 1-42 mu M and seven compounds (9,18,19,22,24,26,28) immobilized 100% human spermatozoa at 1% concentration (w/v). Twenty three compounds (2,3,5,8-26,28) exhibited antifungal activity at 25-50 mu g/mL concentration. Seven compounds (9,18,19,22,24,26,28) showed significant anti-trichomonas and spermicidal activities and also exhibited mild antifungal activity. All the compounds were highly safe towards human cervical cell line (HeLa) as shown by the cell-viability assay of HeLa cells at 200 mu g/mL concentration, whereas nonoxynol-9 (N-9, the marketed spermicidal microbicide) was highly cytotoxic. Therefore, it may be concluded that introduction of the pharmacophore responsible for spermicidal activity into a proven anti-trichomonas structure may lead to a potent dual function microbicide better and safer than N-9. (C) 2009 Elsevier Masson SAS. All rights reserved.