ethyl 3-[6-[3-(phenylmethoxycarbonylamino)propylcarbamoyl]-4,4a,5,6,7,8-hexahydro-3H-oxazireno[3,2-i]indol-4-yl]propanoate | 371974-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 3-[6-[3-(phenylmethoxycarbonylamino)propylcarbamoyl]-4,4a,5,6,7,8-hexahydro-3H-oxazireno[3,2-i]indol-4-yl]propanoate
• CAS: 371974-61-7
• 化学式: C₂₅H₃₅N₃O₆
• 分子量: 473.569
• InChiKey: QTVLHSUTXQTIEP-UHFFFAOYSA-N

物化性质

• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 3-[6-[3-(phenylmethoxycarbonylamino)propylcarbamoyl]-4,4a,5,6,7,8-hexahydro-3H-oxazireno[3,2-i]indol-4-yl]propanoate 在 palladium dihydroxide 氢气 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 14.0h， 生成 Ethyl 3-[5-(3-aminopropylcarbamoyl)-2-oxo-1-azabicyclo[5.2.0]nonan-8-yl]propanoate
  参考文献：
  名称：

  Nonpeptide RGD antagonists: A novel class of mimetics, the 5,8-disubstituted 1-azabicyclo[5.2.0]nonan-2-one lactam

  摘要：

  The 1-azabicyclo[5.2.0]nonan-2-one lactam 1 adequately substituted on both cycles A and B as scaffolds mimics the conformationally constrained beta-turn of the tripeptide RGD signaling motif of fibronectin. Using an in vitro assay, we establish that trans diastereoisomer 1b dissociates a soluble fibronectin-integrin alpha(5)beta(1) complex at concentrations comparable to those of a linear RGDS peptide as a competitor. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00181-1
• 作为产物：
  描述：

  3-(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl)-1H-indole-5-carboxylic acid benzyl ester 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 N-氯代丁二酰亚胺 、 氢气 、 铜 、 间氯过氧苯甲酸 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 70.0 ℃ 、7.09 MPa 条件下， 反应 81.5h， 生成 ethyl 3-[6-[3-(phenylmethoxycarbonylamino)propylcarbamoyl]-4,4a,5,6,7,8-hexahydro-3H-oxazireno[3,2-i]indol-4-yl]propanoate
  参考文献：
  名称：

  Nonpeptide RGD antagonists: A novel class of mimetics, the 5,8-disubstituted 1-azabicyclo[5.2.0]nonan-2-one lactam

  摘要：

  The 1-azabicyclo[5.2.0]nonan-2-one lactam 1 adequately substituted on both cycles A and B as scaffolds mimics the conformationally constrained beta-turn of the tripeptide RGD signaling motif of fibronectin. Using an in vitro assay, we establish that trans diastereoisomer 1b dissociates a soluble fibronectin-integrin alpha(5)beta(1) complex at concentrations comparable to those of a linear RGDS peptide as a competitor. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00181-1

文献信息

• Photochemical Rearrangement of Oxaziridines and Nitrones in the Hexahydroindole Series: A Convenient Synthetic Route to 1-Azabicyclo[5.2.0]nonan-2-ones as Novel RGD Mimetics
  作者：Erika Bourguet、Jean-Louis Baneres、Jean-Pierre Girard、Joseph Parello、Jean-Pierre Vidal、Xavier Lusinchi、Jean-Paul Declercq

  DOI：10.1021/ol016184j

  日期：2001.10.1

  [reaction: see text] Photolysis of oxaziridines a or nitrones b provides a convenient synthetic route to fused bicyclic lactams c adequately substituted on both cycles A and B as scaffolds for mimicking conformationally constrained beta-turn peptides as in the tripeptide RGD signaling motif of fibronectin.

  [反应：参见文本]恶唑烷a或亚硝基b的光解提供了一条简便的合成路线，以合成在环A和B上均被取代的稠合双环内酰胺c，作为模仿纤连蛋白三肽RGD信号转导基序的构象受限的β-转角肽的支架。 。
• Nonpeptide RGD antagonists: A novel class of mimetics, the 5,8-disubstituted 1-azabicyclo[5.2.0]nonan-2-one lactam
  作者：Erika Bourguet、Jean-Louis Banères、Joseph Parello、Xavier Lusinchi、Jean-Pierre Girard、Jean-Pierre Vidal

  DOI：10.1016/s0960-894x(03)00181-1

  日期：2003.5

  The 1-azabicyclo[5.2.0]nonan-2-one lactam 1 adequately substituted on both cycles A and B as scaffolds mimics the conformationally constrained beta-turn of the tripeptide RGD signaling motif of fibronectin. Using an in vitro assay, we establish that trans diastereoisomer 1b dissociates a soluble fibronectin-integrin alpha(5)beta(1) complex at concentrations comparable to those of a linear RGDS peptide as a competitor. (C) 2003 Elsevier Science Ltd. All rights reserved.