benzyl (5R)-6-(benzylamino)-5-[(4R)-4-[(tert-butoxycarbonyl)amino]-3-oxo-3,4,5,10-tetrahydroazepino[3,4-b]indol-2(1H)-yl]-6-oxohexylcarbamate | 945534-35-0

• 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: benzyl (5R)-6-(benzylamino)-5-[(4R)-4-[(tert-butoxycarbonyl)amino]-3-oxo-3,4,5,10-tetrahydroazepino[3,4-b]indol-2(1H)-yl]-6-oxohexylcarbamate
• 英文别名: benzyl N-[(5S)-6-(benzylamino)-5-[(4R)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxo-1,4,5,10-tetrahydroazepino[3,4-b]indol-2-yl]-6-oxohexyl]carbamate
• CAS: 945534-35-0
• 化学式: C₃₈H₄₅N₅O₆
• 分子量: 667.805
• InChiKey: MBWFORWGHNUFMJ-VTIYRKAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl (5R)-6-(benzylamino)-5-[(4R)-4-[(tert-butoxycarbonyl)amino]-3-oxo-3,4,5,10-tetrahydroazepino[3,4-b]indol-2(1H)-yl]-6-oxohexylcarbamate 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 benzyl (5R)-6-(benzylamino)-5-[(4R)-4-[(3,3-diphenylpropanoyl)amino]-3-oxo-3,4,5,10-tetrahydroazepino[3,4-b]indol-2(1H)-yl]-6-oxohexylcarbamate
  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：

  Boc-2'-formyl tryptophan 在 N-甲基吗啉 、 吡啶 、 sodium cyanoborohydride 、 magnesium sulfate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 benzyl (5R)-6-(benzylamino)-5-[(4R)-4-[(tert-butoxycarbonyl)amino]-3-oxo-3,4,5,10-tetrahydroazepino[3,4-b]indol-2(1H)-yl]-6-oxohexylcarbamate
  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

文献信息

• Highly Potent 4-Amino-indolo[2,3-<i>c</i>]azepin-3-one-Containing Somatostatin Mimetics with a Range of sst Receptor Selectivities
  作者：Debby Feytens、Magali De Vlaeminck、Renzo Cescato、Dirk Tourwé、Jean Claude Reubi

  DOI：10.1021/jm801205x

  日期：2009.1.8

  conformational analysis of 4-amino-indolo[2,3-c]azepin-3-one (Aia)-containing SRIF mimetics are reported. Different subtype selectivities are observed depending on the N- and C-terminal substituents of the d-Aia-Lys dipeptide mimetic. An sst5-selective analogue with subnanomolar binding affinity was obtained that is the most potent agonist reported to date. A nonselective mimetic with high potency was also

  合成，生物学评估和构象分析的4-氨基吲哚[2,3 - c ] azepin-3-one（Aia）含SRIF模拟。根据d -Aia-Lys二肽模拟物的N-和C-末端取代基，观察到不同的亚型选择性。获得了具有亚纳摩尔结合亲和力的sst 5-选择性类似物，其是迄今为止报道的最有效的激动剂。还鉴定了具有高效力的非选择性模拟物。这项研究可以更好地定义生长抑素药效团中必不可少的d- Trp侧链的生物活性构象。