(4S,7S,10S,13S,16R,19S,22S,25S)-25-Amino-13-(4-amino-butyl)-7,19,22-tribenzyl-10-((R)-1-hydroxy-ethyl)-16-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24-heptaoxo-1,2-dithia-5,8,11,14,17,20,23-heptaaza-cyclohexacosane-4-carboxylic acid | 1025712-68-8

• 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: (4S,7S,10S,13S,16R,19S,22S,25S)-25-Amino-13-(4-amino-butyl)-7,19,22-tribenzyl-10-((R)-1-hydroxy-ethyl)-16-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24-heptaoxo-1,2-dithia-5,8,11,14,17,20,23-heptaaza-cyclohexacosane-4-carboxylic acid
• 英文别名: (4S,7S,10S,13S,16R,19S,22S,25S)-25-amino-13-(4-aminobutyl)-7,19,22-tribenzyl-10-[(1R)-1-hydroxyethyl]-16-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24-heptaoxo-1,2-dithia-5,8,11,14,17,20,23-heptazacyclohexacosane-4-carboxylic acid
• CAS: 1025712-68-8
• 化学式: C₅₄H₆₆N₁₀O₁₀S₂
• 分子量: 1079.31
• InChiKey: PJRZZHKHLDKTKL-XQLDPLCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  76
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  380
• 氢给体数：
  12
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  BOC-L-苯丙氨酸 、 N-Boc-O-苄基-L-苏氨酸 、 N-叔丁氧羰基-N'-(2-氯苄氧羰基)-L-赖氨酸 、 BOC-D-色氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (4S,7S,10S,13S,16R,19S,22S,25S)-25-Amino-13-(4-amino-butyl)-7,19,22-tribenzyl-10-((R)-1-hydroxy-ethyl)-16-(1H-indol-3-ylmethyl)-6,9,12,15,18,21,24-heptaoxo-1,2-dithia-5,8,11,14,17,20,23-heptaaza-cyclohexacosane-4-carboxylic acid
  参考文献：
  名称：

  Ring Size of Somatostatin Analogues (ODT-8) Modulates Receptor Selectivity and Binding Affinity

  摘要：

  The synthesis, biological testing, and NMR studies of several analogues of H-c[Cys(3) -Phe(6) -Phe(7) -DTrp(8)- Lys(9)-Thr(10)-Phe(11)-CYS(14)] -OH (ODT-8, a pan-somatostatin analogue, 1) have been performed to assess the effect of changing the stereochemistry and the number of atoms in the disulfide bridge on binding affinity. Cysteine at positions 3 and/or 14 (somatostatin numbering) were/was substituted with D-Cysteine, norcysteine, D-norcysteine, homocysteine, and/or D-homocysteine. The 3D structure analysis of selected partially selective, bioactive analogues (3, 18, 19, and 21) was carried out in dim ethyl sulfoxide. Interestingly and not unexpectedly, the 3D structures of these analogues comprised the pharmacophore for which the analogues had the highest binding affinities (i.e., sst(4) in all cases).

  DOI：

  10.1021/jm701444y

文献信息

• Ring Size of Somatostatin Analogues (ODT-8) Modulates Receptor Selectivity and Binding Affinity
  作者：Judit Erchegyi、Christy Rani R. Grace、Manoj Samant、Renzo Cescato、Veronique Piccand、Roland Riek、Jean Claude Reubi、Jean E. Rivier

  DOI：10.1021/jm701444y

  日期：2008.5.1

  The synthesis, biological testing, and NMR studies of several analogues of H-c[Cys(3) -Phe(6) -Phe(7) -DTrp(8)- Lys(9)-Thr(10)-Phe(11)-CYS(14)] -OH (ODT-8, a pan-somatostatin analogue, 1) have been performed to assess the effect of changing the stereochemistry and the number of atoms in the disulfide bridge on binding affinity. Cysteine at positions 3 and/or 14 (somatostatin numbering) were/was substituted with D-Cysteine, norcysteine, D-norcysteine, homocysteine, and/or D-homocysteine. The 3D structure analysis of selected partially selective, bioactive analogues (3, 18, 19, and 21) was carried out in dim ethyl sulfoxide. Interestingly and not unexpectedly, the 3D structures of these analogues comprised the pharmacophore for which the analogues had the highest binding affinities (i.e., sst(4) in all cases).