3-[[3-[(4-Cyanophenyl)methyl]imidazol-4-yl]methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoic acid | 905858-58-4

• 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-[[3-[(4-Cyanophenyl)methyl]imidazol-4-yl]methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoic acid
• CAS: 905858-58-4
• 化学式: C₂₀H₂₄N₄O₄
• 分子量: 384.435
• InChiKey: YOJKTDHPLWGSHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[[3-[(4-Cyanophenyl)methyl]imidazol-4-yl]methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoic acid 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-(3-{[3-(4-cyano-benzyl)-3H-imidazol-4-ylmethyl]-amino}-propionylamino)-3-phenyl-propionamide; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Solid-phase synthesis and pharmacological evaluation of a library of peptidomimetics as potential farnesyltransferase inhibitors: an approach to new lead compounds

  摘要：

  Oncogenic Ras proteins whose activation is farnesylation by farnesyltransferase have been seen as important targets for novel anticancer drugs. Inhibitors of this enzyme have already been developed as potential anti-cancer drugs, particularly by rational design based on the structure of the CA(1)A(2)X carboxyl terminus of Ras. Synthesis of a peptidomimetics library via solid-phase synthesis using the Multipin (TM) method is described here. The most active hits on cellular assays were resynthesized and enzymatic activity was measured. Compounds A1, A5 and A7 present significant activity on the isolated enzyme (IC50 = 117, 57.3 and 28.5 nM) and their molecular docking in the active site of the enzyme provides details on key interactions with the protein. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.03.017
• 作为产物：
  描述：

  4-(5-甲酰基-1-咪唑甲基)苯甲腈 在 sodium hydroxide 、 3 A molecular sieve 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 37.0h， 生成 3-[[3-[(4-Cyanophenyl)methyl]imidazol-4-yl]methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoic acid
  参考文献：
  名称：

  Solid-phase synthesis and pharmacological evaluation of a library of peptidomimetics as potential farnesyltransferase inhibitors: an approach to new lead compounds

  摘要：

  Oncogenic Ras proteins whose activation is farnesylation by farnesyltransferase have been seen as important targets for novel anticancer drugs. Inhibitors of this enzyme have already been developed as potential anti-cancer drugs, particularly by rational design based on the structure of the CA(1)A(2)X carboxyl terminus of Ras. Synthesis of a peptidomimetics library via solid-phase synthesis using the Multipin (TM) method is described here. The most active hits on cellular assays were resynthesized and enzymatic activity was measured. Compounds A1, A5 and A7 present significant activity on the isolated enzyme (IC50 = 117, 57.3 and 28.5 nM) and their molecular docking in the active site of the enzyme provides details on key interactions with the protein. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.03.017