N-Boc-Pro-ψ(NHCH2)-N-methyl-leucine benzyl ester | 333363-48-7

• 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-Boc-Pro-ψ(NHCH2)-N-methyl-leucine benzyl ester
• 英文别名: tert-butyl (2S)-2-[[methyl-[(2R)-4-methyl-1-oxo-1-phenylmethoxypentan-2-yl]amino]methyl]pyrrolidine-1-carboxylate
• CAS: 333363-48-7
• 化学式: C₂₄H₃₈N₂O₄
• 分子量: 418.577
• InChiKey: FJVJCBYPMHEHKU-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-Boc-Pro-ψ(NHCH2)-N-methyl-leucine benzyl ester 在 N-甲基吗啉 、 盐酸 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 L-lactyl-Pro-ψ(NHCH2)-N-methyl-D-leucine 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
• 作为产物：
  描述：

  Boc-L-脯氨酸甲酯 在 sodium tetrahydroborate 、 pyridine-SO3 complex 、 乙醇 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-Boc-Pro-ψ(NHCH2)-N-methyl-leucine 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

文献信息

• Synthetic Studies of Tamandarin B Side Chain Analogues
  作者：Kenneth M. Lassen、Jisun Lee、Madeleine M. Joullié

  DOI：10.1021/jo100457w

  日期：2010.5.7

  The syntheses of three tamandarin B analogues are described. The goal of these studies was to prepare material to determine their relative therapeutic index and to gain an oversight as to their potential for clinical applications.