methyl N-[6-(4-fluorobenzoyl)-1-(phosphonooxymethyl)benzimidazol-2-yl]carbamate | 923672-32-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl N-[6-(4-fluorobenzoyl)-1-(phosphonooxymethyl)benzimidazol-2-yl]carbamate
• CAS: 923672-32-6
• 化学式: C₁₇H₁₅FN₃O₇P
• 分子量: 423.294
• InChiKey: LJRLXRLDYLJXOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  氟苯咪唑 、 二叔丁基氯甲基磷酸酯 在 sodium hydride 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 methyl N-[5-(4-fluorobenzoyl)-1-(phosphonooxymethyl)benzimidazol-2-yl]carbamate 、 methyl N-[6-(4-fluorobenzoyl)-1-(phosphonooxymethyl)benzimidazol-2-yl]carbamate
  参考文献：
  名称：

  Highly Water-Soluble Prodrugs of Anthelmintic Benzimidazole Carbamates: Synthesis, Pharmacodynamics, and Pharmacokinetics

  摘要：

  Highly water-soluble prodrugs 1a - g of anthelmintic benzimidazole carbamates 2a - g were synthesized. These prodrugs combine high aqueous solubility and stability with high lability in the presence of alkaline phosphatases. The veterinary utility of 1a was shown by a pharmacodynamic and pharmacokinetic study performed. in swine. Comparable anthelmintic efficacy was observed with prodrug la or the parent fenbendazole 2a. The pharmacokinetic results showed that 2a is better absorbed when derived from 1a than when applied as such.

  DOI：

  10.1021/jm701456r

文献信息

• Highly Water-Soluble Prodrugs of Anthelmintic Benzimidazole Carbamates: Synthesis, Pharmacodynamics, and Pharmacokinetics
  作者：C. Chassaing、M. Berger、A. Heckeroth、T. Ilg、M. Jaeger、C. Kern、K. Schmid、M. Uphoff

  DOI：10.1021/jm701456r

  日期：2008.3.13

  Highly water-soluble prodrugs 1a - g of anthelmintic benzimidazole carbamates 2a - g were synthesized. These prodrugs combine high aqueous solubility and stability with high lability in the presence of alkaline phosphatases. The veterinary utility of 1a was shown by a pharmacodynamic and pharmacokinetic study performed. in swine. Comparable anthelmintic efficacy was observed with prodrug la or the parent fenbendazole 2a. The pharmacokinetic results showed that 2a is better absorbed when derived from 1a than when applied as such.