N-t-butoxycarbonyl-L-isoleucine-phenethylamide | 157325-01-4

• 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: N-t-butoxycarbonyl-L-isoleucine-phenethylamide
• 英文别名: tert-butyl N-[(2S,3S)-3-methyl-1-oxo-1-(2-phenylethylamino)pentan-2-yl]carbamate
• CAS: 157325-01-4
• 化学式: C₁₉H₃₀N₂O₃
• 分子量: 334.459
• InChiKey: SBGWWWVNDWLAPI-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-t-butoxycarbonyl-L-isoleucine-phenethylamide 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 tert-butyl N-[(2S)-1-[[(2S,3S)-3-methyl-1-oxo-1-(2-phenylethylamino)pentan-2-yl]amino]propan-2-yl]carbamate
  参考文献：
  名称：

  Pseudodipeptide Inhibitors of Protein Farnesyltransferase

  摘要：

  A series of pseudodipeptide amides are described that inhibit Ras protein farnesyltransferase (PFTase). These inhibitors are truncated versions of the C-terminal tetrapeptide (CAAX motif) of Ras that serves as the signal sequence for PFTase-catalyzed protein farnesylation. In contrast to CAAX peptidomimetics previously reported, these inhibitors do not have a C-terminal carboxyl moiety, yet they inhibit farnesylation in vitro at <100 nM. Despite the absence of the X residue in the CAAX motif, which normally directs prenylation specificity, these pseudodipeptides are greater than 100-fold selective for PFTase over type 1 protein geranylgeranyltransferase.

  DOI：

  10.1021/jm00020a010
• 作为产物：
  描述：

  BOC-L-异亮氨酸 、 2-苯乙胺 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-t-butoxycarbonyl-L-isoleucine-phenethylamide
  参考文献：
  名称：

  Pseudodipeptide Inhibitors of Protein Farnesyltransferase

  摘要：

  A series of pseudodipeptide amides are described that inhibit Ras protein farnesyltransferase (PFTase). These inhibitors are truncated versions of the C-terminal tetrapeptide (CAAX motif) of Ras that serves as the signal sequence for PFTase-catalyzed protein farnesylation. In contrast to CAAX peptidomimetics previously reported, these inhibitors do not have a C-terminal carboxyl moiety, yet they inhibit farnesylation in vitro at <100 nM. Despite the absence of the X residue in the CAAX motif, which normally directs prenylation specificity, these pseudodipeptides are greater than 100-fold selective for PFTase over type 1 protein geranylgeranyltransferase.

  DOI：

  10.1021/jm00020a010

文献信息

• Inhibitors of farnesyl protein transferase
  申请人：Merck & Co., Inc.

  公开号：US05352705A1

  公开（公告）日：1994-10-04

  The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.

  本发明涉及抑制法尼醇-蛋白质转移酶（FTase）和致癌基因蛋白Ras的法尼酰化的化合物。本发明还涉及包含本发明化合物的化疗组合物以及抑制法尼醇-蛋白质转移酶和致癌基因蛋白Ras的法尼酰化的方法。
• INHIBITORS OF FARNESYL PROTEIN TRANSFERASE
  申请人：Merck & Co., Inc. (a New Jersey corp.)

  公开号：EP0664789A1

  公开（公告）日：1995-08-02
• EP0664789A4
  申请人：——

  公开号：EP0664789A4

  公开（公告）日：1995-09-06
• US5352705A
  申请人：——

  公开号：US5352705A

  公开（公告）日：1994-10-04
• US5504115A
  申请人：——

  公开号：US5504115A

  公开（公告）日：1996-04-02