N-trifluoroacetyl-(2S)-proline methyl ester | 715-58-2

• 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-trifluoroacetyl-(2S)-proline methyl ester
• 英文别名: 1-trifluoroacetyl-L-proline-methyl ester；1-Trifluoracetyl-L-prolin-methylester；N-Tfa-L-proline methyl ester；methyl (2S)-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxylate
• CAS: 715-58-2
• 化学式: C₈H₁₀F₃NO₃
• 分子量: 225.168
• InChiKey: SZHIHLKFIRSJER-YFKPBYRVSA-N

物化性质

• 沸点：
  260.6°C (rough estimate)
• 密度：
  1.364±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L-脯氨酸 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 生成 N-trifluoroacetyl-(2S)-proline methyl ester
  参考文献：
  名称：

  Cycloforskamide, a Cytotoxic Macrocyclic Peptide from the Sea Slug Pleurobranchus forskalii

  摘要：

  A macrocylic dodecapeptide, cycloforskamide, was isolated from the sea slug Pleurobranchus forskalii, collected off Ishigaki Island, Japan. Its planar structure was deduced by extensive NMR analyses and was further confirmed by MS/MS fragmentation analyses. Finally, the absolute configuration was determined by total hydrolysis and chiral-phase gas chromatographic analysis. This novel dodecapeptide contains three D-amino acids and three thiazoline heterocycles and exhibits cytotoxicity against murine leukemia P388 cells, with an IC50 of 5.8 mu M.

  DOI：

  10.1021/np400404r

文献信息

• Modulation of an n→π* interaction with α-fluoro groups
  作者：Amit Choudhary、Charles G. Fry、Ronald T. Raines

  DOI：10.3998/ark.5550190.0011.817

  日期：——

  Noncovalent interactions play an essential role in biological and chemical processes. In the main chain of common protein secondary structures, the lone pair (n) of a carbonyl oxygen is delocalized into the antibonding orbital (π*) of the subsequent carbonyl group. Herein, experimental and computational data reveal that this n→π* interaction can be attenuated by the inductive electron withdrawal of

  非共价相互作用在生物和化学过程中起着至关重要的作用。在常见蛋白质二级结构的主链中，羰基氧的孤对 (n) 离域到后续羰基的反键轨道 (π*) 中。在此，实验和计算数据表明，这种 n→π* 相互作用可以通过供体中一个或两个 α-氟基团的感应电子撤回减弱。然而，三个 α-氟基团的空间效应克服了诱导撤回。这些数据引发了一种调节肽、蛋白质和其他系统中 n→π* 相互作用的方法。
• Novel pyrazolopyrimidines as cyclin dependent kinase inhibitors
  申请人：Guzi J. Timothy

  公开号：US20070281951A1

  公开（公告）日：2007-12-06

  In its many embodiments, the present invention provides a novel class of pyrazolo[1,5-a]pyrimidine compounds as inhibitors of cyclin dependent kinases, methods of preparing such compounds, compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the CDKs using such compounds or compositions.

  在其许多实施例中，本发明提供了一种新型的嘧唑并[1,5-a]嘧啶类化合物作为细胞周期依赖性激酶抑制剂，制备这种化合物的方法，含有一种或多种此类化合物的组合物，制备包含一种或多种此类化合物的制药配方的方法，并使用这种化合物或组合物进行一种或多种与CDK相关的疾病的治疗、预防、抑制或改善的方法。
• Pyrazolopyrimidines as cyclin dependent kinase inhibitors
  申请人：Guzi J. Timothy

  公开号：US20070225270A1

  公开（公告）日：2007-09-27

  In its many embodiments, the present invention provides a novel class of pyrazolo[1,5-a]pyrimidine compounds as inhibitors of cyclin dependent kinases, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the CDKs using such compounds or pharmaceutical compositions.

  在其多种实施方式中，本发明提供了一种新型的嘧唑并[1,5-a]嘧啶化合物类作为细胞周期蛋白依赖性激酶的抑制剂，制备这种化合物的方法，含有一种或多种这种化合物的制药组合物，制备包含一种或多种这种化合物的制药制剂的方法，以及使用这种化合物或制药组合物治疗、预防、抑制或缓解与CDKs相关的一种或多种疾病的方法。
• Kinetic Resolution of Protected α-Amino Acid Derivatives by a Chiral <i>O</i>-Nucleophilic Acyl Transfer Catalyst
  作者：Gregory T. Notte、Tarek Sammakia

  DOI：10.1021/ja058010t

  日期：2006.4.5

  The kinetic resolution of alpha-trifluoroacetamido N-acyl oxazolidinethiones using 5-10% of the chiral, nonracemic O-nucleophilic acyl transfer catalyst 2 is described. A variety of substrates participate in this reaction in excellent yields, with s-factors ranging from 20 to 86.
• Psychrophilin E, a new cyclotripeptide, from co-fermentation of two marine alga-derived fungi of the genus <i>Aspergillus</i>
  作者：Sherif S. Ebada、Thomas Fischer、Alexandra Hamacher、Feng-Yu Du、Yoen Ok Roth、Matthias U. Kassack、Bin-Gui Wang、Eckhard H. Roth

  DOI：10.1080/14786419.2014.880911

  日期：2014.6.3

  Chemical investigation of the mycelial extract of a mixed culture of two marine alga-derived fungal strains of the genus Aspergillus has yielded one new cyclotripeptide, psychrophilin E (1), the recently reported oxepin-containing alkaloids, protuboxepin A (2) and oxepinamide E (3), together with three other polyketide derivatives (4-6). The chemical structure and relative and absolute configurations of psychrophilin E (1) were unambiguously established based on HRMS, 1D, 2D NMR and chiral-phase HPLC analysis of its hydrolysate. All the isolated compounds were assessed for their anti-proliferative activity against four different human cancer cell lines and some of them revealed selective activities.