[(S)-1-(2-Hydroxy-ethylthiocarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester | 142342-81-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(S)-1-(2-Hydroxy-ethylthiocarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester
• CAS: 142342-81-2
• 化学式: C₁₆H₂₄N₂O₃S
• 分子量: 324.444
• InChiKey: RZYABEYHQMCWCM-ZDUSSCGKSA-N

物化性质

• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.59
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(S)-1-(2-Hydroxy-ethylthiocarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 (1S)-1-(4,5-dihydro-1,3-thiazol-2-yl)-2-phenylethanamine;2,2,2-trifluoroacetic acid
  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：

  在 劳森试剂 、 四丁基氟化铵 作用下， 以 苯 为溶剂， 反应 2.5h， 生成 [(S)-1-(2-Hydroxy-ethylthiocarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester
  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

• Formation of oxazolines and thiazolines in peptides by the mitsunobu reaction
  作者：Nathalie Galéotti、Corine Montagne、Joël Poncet、Patrick Jouin

  DOI：10.1016/s0040-4039(00)78864-2

  日期：1992.5

  The Mitsunobu reaction was efficiently used to introduce oxazolines and thiazolines in the peptide backbone. The reaction proceeded from beta-hydroxy alpha-amino acid-containing peptides at room temperature in 58-72% isolated yields.