ethyl (2S)-3-(2-oxo-3H-benzimidazol-1-yl)-2-(prop-2-enoxycarbonylamino)propanoate | 488118-69-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (2S)-3-(2-oxo-3H-benzimidazol-1-yl)-2-(prop-2-enoxycarbonylamino)propanoate
• CAS: 488118-69-0
• 化学式: C₁₆H₁₉N₃O₅
• 分子量: 333.344
• InChiKey: HYWABRNECZDEBN-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (2S)-3-(2-oxo-3H-benzimidazol-1-yl)-2-(prop-2-enoxycarbonylamino)propanoate 在 sodium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以93%的产率得到(2S)-3-(2-oxo-3H-benzimidazol-1-yl)-2-(prop-2-enoxycarbonylamino)propanoic acid
  参考文献：
  名称：

  (1-Benzimidazolonyl)alanine (Bia): preliminary investigations into a potential tryptophan mimetic

  摘要：

  The new amino acid (1-benzimidazolonyl)alanine (Bia) was synthesized as a potential biomimetic replacement of tryptophan. The replacement of tryptophan with this amino acid in a truncated analog of p53 showed nearly identical binding to HDM2 as the same length of the natural peptide. Similar peptides containing 1- and 2-naphthylalanine in lieu of Trp showed weaker binding than either of the other peptides. The synthesis of Bia and the binding of the p53 analogs to HDM2 are reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01501-0
• 作为产物：
  描述：

  乙基(2S)-3-氨基-2-{[(苄氧基)羰基]氨基}丙酸酯 在 palladium on activated charcoal 吡啶 、 N-羟基丁二酰亚胺 、 TEA 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 56.0h， 生成 ethyl (2S)-3-(2-oxo-3H-benzimidazol-1-yl)-2-(prop-2-enoxycarbonylamino)propanoate
  参考文献：
  名称：

  (1-Benzimidazolonyl)alanine (Bia): preliminary investigations into a potential tryptophan mimetic

  摘要：

  The new amino acid (1-benzimidazolonyl)alanine (Bia) was synthesized as a potential biomimetic replacement of tryptophan. The replacement of tryptophan with this amino acid in a truncated analog of p53 showed nearly identical binding to HDM2 as the same length of the natural peptide. Similar peptides containing 1- and 2-naphthylalanine in lieu of Trp showed weaker binding than either of the other peptides. The synthesis of Bia and the binding of the p53 analogs to HDM2 are reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01501-0

文献信息

• (1-Benzimidazolonyl)alanine (Bia): preliminary investigations into a potential tryptophan mimetic
  作者：Vincent J Huber、Thomas W Arroll、Christopher Lum、Burton A Goodman、Hiroshi Nakanishi

  DOI：10.1016/s0040-4039(02)01501-0

  日期：2002.9

  The new amino acid (1-benzimidazolonyl)alanine (Bia) was synthesized as a potential biomimetic replacement of tryptophan. The replacement of tryptophan with this amino acid in a truncated analog of p53 showed nearly identical binding to HDM2 as the same length of the natural peptide. Similar peptides containing 1- and 2-naphthylalanine in lieu of Trp showed weaker binding than either of the other peptides. The synthesis of Bia and the binding of the p53 analogs to HDM2 are reported. (C) 2002 Elsevier Science Ltd. All rights reserved.