N-((5S,11S,14S)-5-((1H-indol-3-yl)methyl)-1-amino-11-benzyl-8,8-dimethyl-1,4,7,10,13-pentaoxo-15-phenyl-3,6,9,12-tetraazapentadecan-14-yl)-2-amino-2-methylpropanamide | 1198110-18-7

• 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
• 英文名称: N-((5S,11S,14S)-5-((1H-indol-3-yl)methyl)-1-amino-11-benzyl-8,8-dimethyl-1,4,7,10,13-pentaoxo-15-phenyl-3,6,9,12-tetraazapentadecan-14-yl)-2-amino-2-methylpropanamide
• 英文别名: [Aib]FF[Aib]WG-NH2
• CAS: 1198110-18-7
• 化学式: C₃₉H₄₈N₈O₆
• 分子量: 724.86
• InChiKey: BCGXCESTFTYCOK-CHQNGUEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  53.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  230.4
• 氢给体数：
  8.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  Fmoc-甘氨酸 、 Fmoc-L-苯丙氨酸 、 Fmoc-2-氨基异丁酸 、 Fmoc-L-色氨酸(Boc)-OH 在 1-羟基苯并三唑 、 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 2.33h， 生成 N-((5S,11S,14S)-5-((1H-indol-3-yl)methyl)-1-amino-11-benzyl-8,8-dimethyl-1,4,7,10,13-pentaoxo-15-phenyl-3,6,9,12-tetraazapentadecan-14-yl)-2-amino-2-methylpropanamide
  参考文献：
  名称：

  Design, synthesis and aphicidal activity of N-terminal modified insect kinin analogs

  摘要：

  The insect kinins are a class of multifunctional insect neuropeptides present in a diverse variety of insects. Insect kinin analogs showed multiple bioactivities, especially, the aphicidal activity. To find a biostable and bioactive insecticide candidate with simplified structure, a series of N-terminal modified insect kinin analogs was designed and synthesized based on the lead compound [Aib]-Phe-Phe-[Aib]-Trp-Gly-NH2. Their aphicidal activity against the soybean aphid Aphis glycines was evaluated. The results showed that all the analogs maintained the aphicidal activity. In particular, the aphicidal activity of the pentapeptide analog X Phe-Phe-[Aib]-Trp-Gly-NH2 (LC50 = 0.045 mmol/L) was similar to the lead compound (LC50 = 0.048 mmol/L). This indicated that the N-terminal protective group may not play an important role in the activity and the analogs structure could be simplified to pentapeptide analogs while retaining good aphicidal activity. The core pentapeptide analog X can be used as the lead compound for further chemical modifications to discover potential insecticides. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.peptides.2014.07.028