tert-butyl (2S)-2-phenyl-4-{[(trifluoromethyl)sulfonyl]oxy}-2,5-dihydro-1H-pyrrole-1-carboxylate | 635724-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: tert-butyl (2S)-2-phenyl-4-{[(trifluoromethyl)sulfonyl]oxy}-2,5-dihydro-1H-pyrrole-1-carboxylate
• 英文别名: (2S)-tert-butyl 2-phenyl-4-{[(trifluoromethyl)sulfonyl]oxy}-2,5-dihydro-1H-pyrrole-1-carboxylate；tert-butyl(2S)-2-phenyl-4-{[(trifluoromethyl)sulfonyl]oxy}-2,5-dihydro-1H-pyrrole-1-carboxylate；tert-butyl (2S)-2-phenyl-4-(trifluoromethylsulfonyloxy)-2,5-dihydropyrrole-1-carboxylate
• CAS: 635724-47-9
• 化学式: C₁₆H₁₈F₃NO₅S
• 分子量: 393.384
• InChiKey: ZOOIISWGQHRVGL-ZDUSSCGKSA-N

物化性质

• 沸点：
  445.0±45.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-phenyl-4-{[(trifluoromethyl)sulfonyl]oxy}-2,5-dihydro-1H-pyrrole-1-carboxylate 在 四(三苯基膦)钯 、 sodium carbonate 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 (S)-4-(2,5-Difluoro-phenyl)-2-phenyl-2,5-dihydro-1H-pyrrole
  参考文献：
  名称：

  Kinesin spindle protein (KSP) inhibitors. Part 2: The design, synthesis, and characterization of 2,4-diaryl-2,5-dihydropyrrole inhibitors of the mitotic kinesin KSP

  摘要：

  The evolution of 2,4-diaryl-2,5-dihydropyrroles as inhibitors of KSP is described. Introduction of basic amide and urea moieties to the dihydropyrrole nucleus enhanced potency and aqueous solubility, simultaneously, and provided compounds that caused mitotic arrest of A2780 human ovarian carcinoma cells with EC(50)s < 10 nM. Ancillary hERG activity was evaluated for this series of inhibitors. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.030
• 作为产物：
  描述：

  2-[N,正双(三氟甲烷烷磺酰)氨基]-5-氯吡啶 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 tert-butyl (2S)-2-phenyl-4-{[(trifluoromethyl)sulfonyl]oxy}-2,5-dihydro-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  Mitotic kinesin inhibitors

  摘要：

  本发明涉及对治疗细胞增殖性疾病、治疗与KSP动力蛋白活性相关的疾病以及抑制KSP动力蛋白的二氢吡咯化合物。该发明还涉及包含这些化合物的组合物，以及利用它们治疗哺乳动物癌症的方法。

  公开号：

  US20050038074A1

文献信息

• [EN] MITOTIC KINESIN INHIBITORS<br/>[FR] INHIBITEUR DE KINESINES MITOTIQUES
  申请人：MERCK & CO INC

  公开号：WO2003105855A1

  公开（公告）日：2003-12-24

  The present invention relates to dihydropyrrole compounds that are useful for treating cellular proliferative diseases, for treating disorders associated with KSP kinesin activity, and for inhibiting KSP kinesin. The invention also related to compositions which comprise these compounds, and methods of using them to treat cancer in mammals.

  本发明涉及对二氢吡咯烷化合物，其用于治疗细胞增殖性疾病，治疗与KSP动力蛋白活性相关的疾病，以及抑制KSP动力蛋白。该发明还涉及包含这些化合物的组合物，以及使用它们治疗哺乳动物癌症的方法。
• Prodrugs of mitotic kinesin inhibitors
  申请人：Fraley E. Mark

  公开号：US20060135594A1

  公开（公告）日：2006-06-22

  The present invention relates to phosphate ester prodrugs of dihydropyrrole compounds that are useful for treating cellular proliferative diseases, for treating disorders associated with KSP kinesin activity, and for inhibiting KSP kinesin. The invention also related to compositions which comprise these compounds, and methods of using them to treat cancer in mammals.

  本发明涉及磷酸酯前药二氢吡咯烷化合物，用于治疗细胞增殖性疾病、治疗与KSP动力蛋白活性相关的疾病，以及抑制KSP动力蛋白。该发明还涉及包含这些化合物的组合物，以及利用它们治疗哺乳动物癌症的方法。
• [EN] MITOTIC KINESIN INHIBITORS<br/>[FR] INHIBITEURS DE KINESINE MITOTIQUE
  申请人：MERCK & CO INC

  公开号：WO2003106417A1

  公开（公告）日：2003-12-24

  The present invention relates to dihydropyrazole compounds that are useful for treating cellular proliferative diseases, for treating disorders associated with KSP kinesin activity, and for inhibiting KSP kinesin. The invention also related to compositions which comprise these compounds, and methods of using them to treat cancer in mammals.

  本发明涉及二氢吡唑化合物，用于治疗细胞增殖性疾病，治疗与KSP动力蛋白活性相关的疾病，并抑制KSP动力蛋白。该发明还涉及包含这些化合物的组合物，以及使用它们治疗哺乳动物癌症的方法。
• [EN] MITOTIC KINESIN INHIBITORS<br/>[FR] INHIBITEURS DE LA KINESINE MITOTIQUE
  申请人：MERCK & CO INC

  公开号：WO2005019206A1

  公开（公告）日：2005-03-03

  The present invention relates to dihydropyrrole compounds of Formula (I) that are useful for treating cellular proliferative diseases, for treating disorders associated with KSP kinesin activity, and for inhibiting KSP kinesin. The invention is also related to compositions which comprise these compounds, and methods of using them to treat cancer in mammals.

  本发明涉及式(I)的二氢吡咯化合物，其对治疗细胞增殖性疾病、治疗与KSP动力蛋白活性相关的疾病以及抑制KSP动力蛋白具有用途。本发明还涉及包含这些化合物的组合物以及使用它们治疗哺乳动物癌症的方法。
• Mitotic kinesin binding site
  申请人：Buser-Doepner A. Carolyn

  公开号：US20060134767A1

  公开（公告）日：2006-06-22

  The present invention is directed to the identification, characterization and three-dimensional structure of a novel ligand binding site of KSP. Binding of ligands to the novel binding site result in a conformational change in the three-dimensional structure of the protein and a modulation of the activity of KSP. This conformational change in turn results in the formation of a novel binding pocket in the KSP protein, which comprises the novel binding site of the instant invention.

  本发明涉及KSP的新型配体结合位点的鉴定、表征和三维结构。配体与新型结合位点的结合导致蛋白质的三维结构发生构象变化，并调节KSP的活性。这种构象变化进而导致在KSP蛋白质中形成一个新的结合口袋，其中包括本发明的新型结合位点。