(R)-4-Methyl-2-{methyl-[(S)-1-(2-oxo-propionyl)-pyrrolidin-2-ylmethyl]-amino}-pentanoic acid benzyl ester | 333363-53-4

• 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: (R)-4-Methyl-2-{methyl-[(S)-1-(2-oxo-propionyl)-pyrrolidin-2-ylmethyl]-amino}-pentanoic acid benzyl ester
• 英文别名: benzyl (2R)-4-methyl-2-[methyl-[[(2S)-1-(2-oxopropanoyl)pyrrolidin-2-yl]methyl]amino]pentanoate
• CAS: 333363-53-4
• 化学式: C₂₂H₃₂N₂O₄
• 分子量: 388.507
• InChiKey: SOVPADHKRZXIIM-VQTJNVASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-4-Methyl-2-{methyl-[(S)-1-(2-oxo-propionyl)-pyrrolidin-2-ylmethyl]-amino}-pentanoic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以99%的产率得到(R)-4-Methyl-2-{methyl-[(S)-1-(2-oxo-propionyl)-pyrrolidin-2-ylmethyl]-amino}-pentanoic acid
  参考文献：
  名称：

  Structure–activity relationships of side-chain modified didemnins

  摘要：

  The synthesis and antitumor activity of a novel didemnin B analogue containing a Psi [CH2NH] amide bond surrogate between N-Me-D-Leu(7) and pro(8) are reported. The analogue shows activity (GI(50) = 4 nM) comparable to that of didemnin B (GI(50) = 13 nM) in the NCI-60 tumor cell screen. This result, along with new data from previously reported synthetic didemnin analogues, is discussed within the context of the side-chain SAR for didemnins. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00638-7
• 作为产物：
  描述：

  Boc-L-脯氨酸甲酯 在 N-甲基吗啉 、 盐酸 、 sodium tetrahydroborate 、 pyridine-SO3 complex 、 乙醇 、 三乙酰氧基硼氢化钠 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 (R)-4-Methyl-2-{methyl-[(S)-1-(2-oxo-propionyl)-pyrrolidin-2-ylmethyl]-amino}-pentanoic acid benzyl ester
  参考文献：
  名称：

  Structure–activity relationships of side-chain modified didemnins

  摘要：

  The synthesis and antitumor activity of a novel didemnin B analogue containing a Psi [CH2NH] amide bond surrogate between N-Me-D-Leu(7) and pro(8) are reported. The analogue shows activity (GI(50) = 4 nM) comparable to that of didemnin B (GI(50) = 13 nM) in the NCI-60 tumor cell screen. This result, along with new data from previously reported synthetic didemnin analogues, is discussed within the context of the side-chain SAR for didemnins. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00638-7