3-(4-tert-butoxycarbonylamino-imidazol-1-yl)-propionic acid methyl ester | 624720-25-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-tert-butoxycarbonylamino-imidazol-1-yl)-propionic acid methyl ester
• 英文别名: Methyl 3-[4-[(2-methylpropan-2-yl)oxycarbonylamino]imidazol-1-yl]propanoate
• CAS: 624720-25-8
• 化学式: C₁₂H₁₉N₃O₄
• 分子量: 269.301
• InChiKey: APHVBXJDCIXQDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-tert-butoxycarbonylamino-imidazol-1-yl)-propionic acid methyl ester 在 盐酸 、 羟胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-(4-Amino-imidazol-1-yl)-N-hydroxy-propionamide; hydrochloride
  参考文献：
  名称：

  Design and Synthesis of Heterocyclic Hydroxamic Acid Derivatives as Inhibitors ofHelicobacterpyloriUrease

  摘要：

  Helicobacter pylori produces ammonia to help counter the acidic environment in the human stomach. The production of ammonia, essential for the microorganism's survival and virulence, is the product of enzymatic conversion of urea by the H. pylori's urease. Inhibition of urease activity by dipeptide hydroxamic acids has previously been demonstrated using a variety of fluorides, thiols and hydroxamic acids. Studies employing computer-aided drug design techniques have been utilized to suggest a novel series of heterocyclic hydroxamic acid derivatives as potential as urease inhibitors. The heterocyclic compounds 7a,b, 10b, 12b, 16b, and 19b have been designed, synthesized, and preliminarily tested as dipeptide mimics which offer a structure that is more biologically stable than that of the reported dipeptide inhibitors.

  DOI：

  10.1081/scc-120021024
• 作为产物：
  描述：

  3-(4-nitro-imidazol-1-yl)-propionic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 2.0h， 生成 3-(4-tert-butoxycarbonylamino-imidazol-1-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Design and Synthesis of Heterocyclic Hydroxamic Acid Derivatives as Inhibitors ofHelicobacterpyloriUrease

  摘要：

  Helicobacter pylori produces ammonia to help counter the acidic environment in the human stomach. The production of ammonia, essential for the microorganism's survival and virulence, is the product of enzymatic conversion of urea by the H. pylori's urease. Inhibition of urease activity by dipeptide hydroxamic acids has previously been demonstrated using a variety of fluorides, thiols and hydroxamic acids. Studies employing computer-aided drug design techniques have been utilized to suggest a novel series of heterocyclic hydroxamic acid derivatives as potential as urease inhibitors. The heterocyclic compounds 7a,b, 10b, 12b, 16b, and 19b have been designed, synthesized, and preliminarily tested as dipeptide mimics which offer a structure that is more biologically stable than that of the reported dipeptide inhibitors.

  DOI：

  10.1081/scc-120021024