desmocyclopeptide | 1186048-83-8

• 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: desmocyclopeptide
• 英文别名: cyclo[Ala-Gly-Pro-Ile-Phe]；(6S,9S,12S,15S)-9-benzyl-12-[(2S)-butan-2-yl]-6-methyl-1,4,7,10,13-pentazabicyclo[13.3.0]octadecane-2,5,8,11,14-pentone
• CAS: 1186048-83-8
• 化学式: C₂₅H₃₅N₅O₅
• 分子量: 485.583
• InChiKey: NIWFSFAREHOZLG-CJGRYMHTSA-N

物化性质

• 沸点：
  892.4±65.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  137
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  desmocyclopeptide 在 盐酸 作用下， 以 水 为溶剂， 反应 24.0h， 生成 甘氨酸盐酸盐 、 L-苯丙氨酸盐酸盐 、 L-丙氨酸盐酸盐 、 L-异亮氨酸盐酸盐 、 L-脯氨酸盐酸盐
  参考文献：
  名称：

  Novel cyclopeptide and unique flavone from Desmos rostrata. Total synthesis of desmorostratone

  摘要：

  Two new compounds, a cyclic peptide desmocyclopeptide (1) and a special flavone desmorostratone (2) were isolated from the stem bark of Desmos rostrata, along with two known compounds, desmosdumotins B (3) and C (4). Their Structures were established on the basis of the spectral data, including mass spectrometry and 2D NMR. The total synthesis of desmorostratone (2) was performed in order to confirm its structure as well as that of desmosdumotin C (4), which was a tautomeric mixture in the solution. Finally, cytotoxity of these compounds were evaluated. Desmosdumotin C (4) displayed a moderate inhibition activity against KB cell line with an IC50 of 19.2 mu M, whereas the other products showed a weak inhibition against the same cell line target. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.017

文献信息

• Novel cyclopeptide and unique flavone from Desmos rostrata. Total synthesis of desmorostratone
  作者：Ngoc Tuan Nguyen、Van Cuong Pham、Marc Litaudon、Françoise Guéritte、Bernard Bodo、Van Tuyen Nguyen、Van Hung Nguyen

  DOI：10.1016/j.tet.2009.06.017

  日期：2009.8

  Two new compounds, a cyclic peptide desmocyclopeptide (1) and a special flavone desmorostratone (2) were isolated from the stem bark of Desmos rostrata, along with two known compounds, desmosdumotins B (3) and C (4). Their Structures were established on the basis of the spectral data, including mass spectrometry and 2D NMR. The total synthesis of desmorostratone (2) was performed in order to confirm its structure as well as that of desmosdumotin C (4), which was a tautomeric mixture in the solution. Finally, cytotoxity of these compounds were evaluated. Desmosdumotin C (4) displayed a moderate inhibition activity against KB cell line with an IC50 of 19.2 mu M, whereas the other products showed a weak inhibition against the same cell line target. (c) 2009 Elsevier Ltd. All rights reserved.