(R)-4-Methyl-2-{methyl-[(S)-1-(2-oxo-propionyl)-pyrrolidin-2-ylmethyl]-amino}-pentanoic acid | 333363-55-6

• 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
• CAS: 333363-55-6
• 化学式: C₁₅H₂₆N₂O₄
• 分子量: 298.382
• InChiKey: HDPTVDSOCUTJIJ-QWHCGFSZSA-N

物化性质

• 沸点：
  432.6±51.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  77.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,6S,8S,12S,13R,16S,17R,20S,23S)-16-amino-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosane-2,5,7,10,15,19,22-heptone 、 (R)-4-Methyl-2-{methyl-[(S)-1-(2-oxo-propionyl)-pyrrolidin-2-ylmethyl]-amino}-pentanoic acid 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到(2R)-N-[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-12-hydroxy-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]-4-methyl-2-[methyl-[[(2S)-1-(2-oxopropanoyl)pyrrolidin-2-yl]methyl]amino]pentanamide
  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：

  N-Boc-Pro-ψ(NHCH2)-N-methyl-leucine benzyl ester 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 氢气 、 (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 (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