9H-fluoren-9-ylmethyl 5-[(4R)-4-[(tert-butoxycarbonyl)amino]-3-oxo-3,4,5,10-tetrahydroazepino[3,4-b]indol-2(1H)-yl]pentylcarbamate | 945534-34-9

• 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: 9H-fluoren-9-ylmethyl 5-[(4R)-4-[(tert-butoxycarbonyl)amino]-3-oxo-3,4,5,10-tetrahydroazepino[3,4-b]indol-2(1H)-yl]pentylcarbamate
• 英文别名: tert-butyl N-[(4R)-2-[5-(9H-fluoren-9-ylmethoxycarbonylamino)pentyl]-3-oxo-1,4,5,10-tetrahydroazepino[3,4-b]indol-4-yl]carbamate
• CAS: 945534-34-9
• 化学式: C₃₇H₄₂N₄O₅
• 分子量: 622.764
• InChiKey: ZMPOLMYMBCGCSV-JGCGQSQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9H-fluoren-9-ylmethyl 5-[(4R)-4-[(tert-butoxycarbonyl)amino]-3-oxo-3,4,5,10-tetrahydroazepino[3,4-b]indol-2(1H)-yl]pentylcarbamate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 生成 9H-fluoren-9-ylmethyl 5-[(4R)-4-[(3,3-diphenylpropanoyl)amino]-3-oxo-3,4,5,10-tetrahydroazepino[3,4-b]indol-2(1H)-yl]pentylcarbamate
  参考文献：
  名称：

  New sst_4/5-Selective Somatostatin Peptidomimetics Based on a Constrained Tryptophan Scaffold

  摘要：

  The synthesis and biological evaluation of four peptidomimetic analogs of somatostatin based on a constrained Trp residue, 3-amino-indolo[2,3-c]azepin-2-one (Aia), are reported. It is shown that dipeptidomimetics with a d-Aia-Lys sequence, functionalized with N- and C-terminal aromatic substituents, display a good selectivity for both sst(4) and sst(5.) This study allowed us to identify a new highly potent sst(5) agonist with good selectivity over the other receptors, except versus sst(4).

  DOI：

  10.1021/jm070246f
• 作为产物：
  描述：

  (2R)-3-[2-[[5-(9H-fluoren-9-ylmethoxycarbonylamino)pentylamino]methyl]-1H-indol-3-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid 在 吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 水 、 乙腈 为溶剂， 生成 9H-fluoren-9-ylmethyl 5-[(4R)-4-[(tert-butoxycarbonyl)amino]-3-oxo-3,4,5,10-tetrahydroazepino[3,4-b]indol-2(1H)-yl]pentylcarbamate
  参考文献：
  名称：

  New sst_4/5-Selective Somatostatin Peptidomimetics Based on a Constrained Tryptophan Scaffold

  摘要：

  The synthesis and biological evaluation of four peptidomimetic analogs of somatostatin based on a constrained Trp residue, 3-amino-indolo[2,3-c]azepin-2-one (Aia), are reported. It is shown that dipeptidomimetics with a d-Aia-Lys sequence, functionalized with N- and C-terminal aromatic substituents, display a good selectivity for both sst(4) and sst(5.) This study allowed us to identify a new highly potent sst(5) agonist with good selectivity over the other receptors, except versus sst(4).

  DOI：

  10.1021/jm070246f