ethyl 3-[5-[3-(phenylmethoxycarbonylamino)propylcarbamoyl]-3,3a,4,5,6,7-hexahydro-2H-indol-3-yl]propanoate | 586363-99-7

• 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-[5-[3-(phenylmethoxycarbonylamino)propylcarbamoyl]-3,3a,4,5,6,7-hexahydro-2H-indol-3-yl]propanoate
• CAS: 586363-99-7
• 化学式: C₂₅H₃₅N₃O₅
• 分子量: 457.57
• InChiKey: BKSFNRATYSNHBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3-[5-[3-(phenylmethoxycarbonylamino)propylcarbamoyl]-3,3a,4,5,6,7-hexahydro-2H-indol-3-yl]propanoate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 8.5h， 生成 Ethyl 3-[2-oxo-5-[3-(phenylmethoxycarbonylamino)propylcarbamoyl]-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 、 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， 20.0~70.0 ℃ 、7.09 MPa 条件下， 反应 81.0h， 生成 ethyl 3-[5-[3-(phenylmethoxycarbonylamino)propylcarbamoyl]-3,3a,4,5,6,7-hexahydro-2H-indol-3-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

• 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.