(2S,3S)-2-((2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentylamino)-3-methyl-pentanoic acid | 158861-48-4

• 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: (2S,3S)-2-((2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentylamino)-3-methyl-pentanoic acid
• CAS: 158861-48-4
• 化学式: C₁₇H₃₄N₂O₄
• 分子量: 330.468
• InChiKey: NKQQXWFRDJQYTM-FQUUOJAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  23.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  87.66
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-((2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentylamino)-3-methyl-pentanoic acid 在 盐酸 、 三乙基硅烷 、 sodium hydroxide 、 3 A molecular sieve 、 potassium acetate 、 sodium cyanoborohydride 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-{(2S,3S)-2-[(2S,3S)-2-((R)-2-Amino-3-mercapto-propylamino)-3-methyl-pentylamino]-3-methyl-pentanoylamino}-4-methylsulfanyl-butyric acid
  参考文献：
  名称：

  N-Arylalkyl Pseudopeptide Inhibitors of Farnesyltransferase

  摘要：

  Inhibitors of Ras protein farnesyltransferase are described which are reduced pseudopeptides related to the C-terminal tetrapeptide of the Ras protein that signals farnesylation. Reduction of the carbonyl groups linking the first three residues of the tetrapeptide leads to active inhibitors which are chemically unstable. Stability can he restored by alkylating the central amine of the tetrapeptide. Studies of the SAR of these alkylated pseudopeptides with concomitant modification of the side chain of the third residue led to 2(S)-(2(S)-{[2(S)-(2(R)-amino-3-mercaptopropylamino)-3-(S)-methylpentyl]naphthalen-1-ylmethylamino}acetylamino)-4-methylsulfanylbutyric acid (11), a subnanomolar inhibitor. The methyl ester (10) of this compound exhibited submicromolar activity in the processing assay and selectively inhibited anchorage-independent growth of Rat1 cells transformed by v-ras at 2.5-5 mu M.

  DOI：

  10.1021/jm9800907
• 作为产物：
  描述：

  2-甲基-2-丙基[(2S,3S)-3-甲基-1-氧代-2-戊烷基]氨基甲酸酯 在 sodium hydroxide 、 3 A molecular sieve 、 三乙酰氧基硼氢化钠 、 三乙胺 作用下， 以 甲醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,3S)-2-((2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentylamino)-3-methyl-pentanoic acid
  参考文献：
  名称：

  N-Arylalkyl Pseudopeptide Inhibitors of Farnesyltransferase

  摘要：

  Inhibitors of Ras protein farnesyltransferase are described which are reduced pseudopeptides related to the C-terminal tetrapeptide of the Ras protein that signals farnesylation. Reduction of the carbonyl groups linking the first three residues of the tetrapeptide leads to active inhibitors which are chemically unstable. Stability can he restored by alkylating the central amine of the tetrapeptide. Studies of the SAR of these alkylated pseudopeptides with concomitant modification of the side chain of the third residue led to 2(S)-(2(S)-{[2(S)-(2(R)-amino-3-mercaptopropylamino)-3-(S)-methylpentyl]naphthalen-1-ylmethylamino}acetylamino)-4-methylsulfanylbutyric acid (11), a subnanomolar inhibitor. The methyl ester (10) of this compound exhibited submicromolar activity in the processing assay and selectively inhibited anchorage-independent growth of Rat1 cells transformed by v-ras at 2.5-5 mu M.

  DOI：

  10.1021/jm9800907