[Imino-((S)-3-{[(3S,6S,9aS)-6-(naphthalene-1-sulfonylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carbonyl]-amino}-2-oxo-piperidin-1-yl)-methyl]-carbamic acid benzyl ester | 188127-07-3

• 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: [Imino-((S)-3-{[(3S,6S,9aS)-6-(naphthalene-1-sulfonylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carbonyl]-amino}-2-oxo-piperidin-1-yl)-methyl]-carbamic acid benzyl ester
• CAS: 188127-07-3
• 化学式: C₃₄H₃₈N₆O₇S
• 分子量: 674.778
• InChiKey: QCWGESXJTBWYCU-VNNZRSTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  48.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  178.07
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [Imino-((S)-3-{[(3S,6S,9aS)-6-(naphthalene-1-sulfonylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carbonyl]-amino}-2-oxo-piperidin-1-yl)-methyl]-carbamic acid benzyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以61%的产率得到[((S)-2-Hydroxy-3-{[(3S,6S,9aS)-6-(naphthalene-1-sulfonylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carbonyl]-amino}-piperidin-1-yl)-imino-methyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Design and synthesis of conformationally constrained arginal thrombin inhibitors

  摘要：

  A series of conformationally constrained arginal thrombin inhibitors was prepared starting from 5,6 or 5,7 bicyclic lactamic structures, that an indirect approach of X-ray structure-based drug design indicated as D-Phe-Pro dipeptide mimetics. The tetrahydroquinolyl sulfonamido derivative Ig (LR-D/009) displayed the best inhibitory potency (IC50=0.018 mu m), with good selectivity over plasmin and trypsin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00403-4
• 作为产物：
  描述：

  (3S,6S,9aS)-6-(Naphthalene-1-sulfonylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid tert-butyl ester 在 N-甲基吗啉 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [Imino-((S)-3-{[(3S,6S,9aS)-6-(naphthalene-1-sulfonylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carbonyl]-amino}-2-oxo-piperidin-1-yl)-methyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Design and synthesis of conformationally constrained arginal thrombin inhibitors

  摘要：

  A series of conformationally constrained arginal thrombin inhibitors was prepared starting from 5,6 or 5,7 bicyclic lactamic structures, that an indirect approach of X-ray structure-based drug design indicated as D-Phe-Pro dipeptide mimetics. The tetrahydroquinolyl sulfonamido derivative Ig (LR-D/009) displayed the best inhibitory potency (IC50=0.018 mu m), with good selectivity over plasmin and trypsin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00403-4