Boc-(D)-(NⁱBoc)-Trp-(D)-(NⁱBoc)-gTrp-H | 381231-56-7

• 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: Boc-(D)-(NⁱBoc)-Trp-(D)-(NⁱBoc)-gTrp-H
• 英文别名: tert-butyl 3-[(2R)-3-[[(1R)-1-amino-2-[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-3-yl]ethyl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]indole-1-carboxylate
• CAS: 381231-56-7
• 化学式: C₃₆H₄₇N₅O₇
• 分子量: 661.798
• InChiKey: WEVXYQJFFIOFJJ-GGXMVOPNSA-N

物化性质

• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  156
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Boc-(D)-(NⁱBoc)-Trp-(D)-(NⁱBoc)-gTrp-H 在 N-甲基吗啉 、 茴香硫醚 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 苯甲醚 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (2R)-2-(benzenesulfonamido)-N-[(1R)-1-formamido-2-(1H-indol-3-yl)ethyl]-3-(1H-indol-3-yl)propanamide
  参考文献：
  名称：

  New Active Series of Growth Hormone Secretagogues

  摘要：

  New growth hormone secretagogue (GHS) analogues were synthesized and evaluated for growth hormone releasing activity. This series derived from EP-51389 is based on a gem-diamino structure. Compounds that exhibited higher in vivo GH-releasing potency than hexarelin in rat (subcutaneous administration) were then tested per os in beagle dogs and for their binding affinity to human pituitary GHS receptors and to hGHS-R 1a. Compound 7 (JMV 1843, H-Aib-(D)-Trp-(D)-gTrp-formyl) showed high potency in these tests and was selected for clinical studies.(1)

  DOI：

  10.1021/jm020985q
• 作为产物：
  描述：

  Boc-(D)-Trp-(D)-Trp-NH2 在 吡啶 、 4-二甲氨基吡啶 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.0h， 生成 Boc-(D)-(NⁱBoc)-Trp-(D)-(NⁱBoc)-gTrp-H
  参考文献：
  名称：

  New Active Series of Growth Hormone Secretagogues

  摘要：

  New growth hormone secretagogue (GHS) analogues were synthesized and evaluated for growth hormone releasing activity. This series derived from EP-51389 is based on a gem-diamino structure. Compounds that exhibited higher in vivo GH-releasing potency than hexarelin in rat (subcutaneous administration) were then tested per os in beagle dogs and for their binding affinity to human pituitary GHS receptors and to hGHS-R 1a. Compound 7 (JMV 1843, H-Aib-(D)-Trp-(D)-gTrp-formyl) showed high potency in these tests and was selected for clinical studies.(1)

  DOI：

  10.1021/jm020985q

文献信息

• [EN] GROWTH HORMONE SECRETAGOGUES<br/>[FR] SECRETAGOGUES DES HORMONES DE CROISSANCE
  申请人：ZENTARIS AG

  公开号：WO2001096300A1

  公开（公告）日：2001-12-20

  The invention relates to compounds of formula (I) which are useful for elevating the plasma level of growth hormone in a mammal as well as for the treatment of growth hormone secretion deficiency, growth retardation in child and metabolic disorders associated with growth hormone secretion deficiency.

  该发明涉及公式(I)的化合物，该化合物对于提高哺乳动物的血浆生长激素水平以及治疗生长激素分泌缺乏、儿童生长迟缓和与生长激素分泌缺乏相关的代谢紊乱具有用处。
• J. Med. Chem. 2003, 46, 1191-1203
  作者：

  DOI：——

  日期：——
• New Active Series of Growth Hormone Secretagogues
  作者：Vincent Guerlavais、Damien Boeglin、Delphine Mousseaux、Catherine Oiry、Annie Heitz、Romano Deghenghi、Vittorio Locatelli、Antonio Torsello、Corrado Ghé、Filomena Catapano、Giampiero Muccioli、Jean-Claude Galleyrand、Jean-Alain Fehrentz、Jean Martinez

  DOI：10.1021/jm020985q

  日期：2003.3.1

  New growth hormone secretagogue (GHS) analogues were synthesized and evaluated for growth hormone releasing activity. This series derived from EP-51389 is based on a gem-diamino structure. Compounds that exhibited higher in vivo GH-releasing potency than hexarelin in rat (subcutaneous administration) were then tested per os in beagle dogs and for their binding affinity to human pituitary GHS receptors and to hGHS-R 1a. Compound 7 (JMV 1843, H-Aib-(D)-Trp-(D)-gTrp-formyl) showed high potency in these tests and was selected for clinical studies.(1)