| 1402723-94-7

• 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
• CAS: 1402723-94-7
• 化学式: C₃₅H₅₉N₁₁O₁₀
• 分子量: 793.921
• InChiKey: GQNARIQQUDCTNE-MPDUSZQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.72
• 重原子数：
  56.0
• 可旋转键数：
  25.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  353.36
• 氢给体数：
  11.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  Fmoc-L-丙氨酸 、 Fmoc-L-脯氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 Fmoc-O-叔丁基-L-苏氨酸 、 Fmoc-N-三苯甲基-L-天冬酰胺 、 Fmoc-L-烯丙基甘氨酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 、 (3S,6S,11S,14S,17S,20S)-3-(2-amino-2-oxoethyl)-N-[(2S)-1-amino-1-oxopropan-2-yl]-6-[[(2S)-2,6-diaminohexanoyl]amino]-14-[(1R)-1-hydroxyethyl]-17-methyl-2,5,13,16,19-pentaoxo-1,4,12,15,18-pentazabicyclo[18.3.0]tricos-8-ene-11-carboxamide
  参考文献：
  名称：

  How to blast osteoblasts? Novel dicarba analogues of amylin-(1–8) to treat osteoporosis

  摘要：

  When administered in vivo, amylin (1-8) stimulates osteoblast proliferation increasing bone volume and bone strength. The native cyclic octapeptide amylin (1-8) is unstable, however, it provides an attractive framework for the creation of more stable, orally active synthetic analogues using various peptidomimetic techniques. On-resin ring closing metathesis (RCM) on the olefinic side chains of allylglycine residues and lysine moieties functionalized with an allyloxycarbonyl (Alloc) group, was used to prepare novel carba-bridged surrogates of the disulfide bridge between Cys/2 and Cys/7 in amylin-(1-8). Commercially available N-alpha-Fmoc N-epsilon-Alloc protected lysine was used as a convenient substrate for Grubbs' ring closing metathesis. Analogues of amylin-(1-8) prepared by cyclization of allylglycine residues that also contained proline residues at either position 4 or 6, or both, were also prepared to investigate the effect of proline as a 'kink-inducing' residue on the efficiency of the RCM reaction. Of the nine novel alkene-bridged analogues prepared, five showed promising biological activity in a proliferation study in primary foetal rat osteoblasts at physiological concentrations. Two of these analogues were chosen for further in vivo evaluation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.053