ethyl (3R,4S,5S)-3-hydroxy-5-methyl-4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]heptanoate | 1400436-19-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (3R,4S,5S)-3-hydroxy-5-methyl-4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]heptanoate
• CAS: 1400436-19-2
• 化学式: C₁₆H₃₁NO₅
• 分子量: 317.426
• InChiKey: XLCABHPOEHHOKY-SCRDCRAPSA-N

物化性质

• 沸点：
  408.5±38.0 °C(Predicted)
• 密度：
  1.038±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (3R,4S,5S)-3-hydroxy-5-methyl-4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]heptanoate 在 lithium hydroxide monohydrate 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 26.17h， 生成 tert-butyl N-[(2S)-1-[[(3R,4S,5S)-1-[[(2R,3R,4S,5S)-5-(benzylcarbamoyl)-3,4-dimethoxyoxolan-2-yl]methylamino]-3-hydroxy-5-methyl-1-oxoheptan-4-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]carbamate
  参考文献：
  名称：

  A Synthetic Dolastatin 10 Analogue Suppresses Microtubule Dynamics, Inhibits Cell Proliferation, and Induces Apoptotic Cell Death

  摘要：

  We have synthesized eight analogues (D1-D8) of dolastatin 10 containing several unique amino acid subunits. Of these agents, D5 was found to be most effective in inhibiting both He La cell proliferation and microtubule assembly in vitro. At low nanomolar concentrations, 135 inhibited the proliferation of several types of cancer cells in culture. D5 bound to tubulin with a dissociation constant of 29.4 +/- 6 mu M. D5 depolymerized microtubules in cultured cells and produced mulitpolar spindles. At its half-maximal inhibitory concentration (15 nM), DS strongly suppressed the dynamics of individual microtubules in live MCF-7 cells. DS increased the accumulation of checkpoint proteins BubR1 and Mad2 at the kinetochoric region and caused G2/M block in these cells. The blocked cells underwent apoptosis with the activation of Jun N-terminal kinase. The results suggested that DS exerts its antiproliferative action by dampening microtubule dynamics.

  DOI：

  10.1021/jm3009629
• 作为产物：
  描述：

  (1S,2S)-(1-hydroxymethyl-2-methyl-butyl)-methyl-carbamic acid tert-butyl ester 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 ethyl (3R,4S,5S)-3-hydroxy-5-methyl-4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]heptanoate
  参考文献：
  名称：

  A Synthetic Dolastatin 10 Analogue Suppresses Microtubule Dynamics, Inhibits Cell Proliferation, and Induces Apoptotic Cell Death

  摘要：

  We have synthesized eight analogues (D1-D8) of dolastatin 10 containing several unique amino acid subunits. Of these agents, D5 was found to be most effective in inhibiting both He La cell proliferation and microtubule assembly in vitro. At low nanomolar concentrations, 135 inhibited the proliferation of several types of cancer cells in culture. D5 bound to tubulin with a dissociation constant of 29.4 +/- 6 mu M. D5 depolymerized microtubules in cultured cells and produced mulitpolar spindles. At its half-maximal inhibitory concentration (15 nM), DS strongly suppressed the dynamics of individual microtubules in live MCF-7 cells. DS increased the accumulation of checkpoint proteins BubR1 and Mad2 at the kinetochoric region and caused G2/M block in these cells. The blocked cells underwent apoptosis with the activation of Jun N-terminal kinase. The results suggested that DS exerts its antiproliferative action by dampening microtubule dynamics.

  DOI：

  10.1021/jm3009629

文献信息

• Oligopeptides and process for preparation thereof
  申请人：Chakraborty Tushar Kanti

  公开号：US09200034B2

  公开（公告）日：2015-12-01

  This invention relates to oligopeptides having general formula (I). The invention also relates to the process of preparation thereof, wherein the said compounds are selective anti-cancer agents over a panel of human cancer cell lines. Further, this invention relates that said anti-cancer peptides are prepared by a novel method.

  本发明涉及具有一般式(I)的寡肽。该发明还涉及其制备过程，其中所述化合物是对一系列人类癌细胞系具有选择性抗癌活性的抗癌剂。此外，本发明涉及所述抗癌肽是通过一种新颖的方法制备的。
• OLIGOPEPTIDES AND PROCESS FOR PREPARATION THEREOF
  申请人：Council of Scientific & Industrial Research

  公开号：EP2686337B1

  公开（公告）日：2016-11-02
• US9200034B2
  申请人：——

  公开号：US9200034B2

  公开（公告）日：2015-12-01