(+)-versicolamide C | 1429428-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (+)-versicolamide C
• 英文别名: (1S,7S,9R,11S)-1'-hydroxy-7',7',10,10-tetramethylspiro[3,13-diazatetracyclo[5.5.2.01,9.03,7]tetradecane-11,3'-pyrano[2,3-g]indole]-2,2',14-trione
• CAS: 1429428-86-3
• 化学式: C₂₆H₂₉N₃O₅
• 分子量: 463.533
• InChiKey: KGCIBVDLLPYXFL-XRNKBYASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  34
• 可旋转键数：
  0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  99.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲醇 、 N-hydroxy-6-epi-stephacidin A 以 二甲基亚砜 为溶剂， 反应 72.0h， 以7.1%的产率得到6-epi-avrainvillamide
  参考文献：
  名称：

  Isolation and Photoinduced Conversion of 6-epi-Stephacidins from Aspergillus taichungensis

  摘要：

  Three prenylated indole alkaloids with a rare anti bicyclo-[2.2.2]diazaoctane core ring (5-7) were isolated from Aspergillus taichungensis. The structures including absolute configurations were elucidated based on NMR, X-ray, and CD methods. (+)-Versicolamides B and C (8-9) which contain a spiro-center, together with seven analogues (7, 10-15), were isolated as photoinduced conversion products of 6. Biological evaluation indicated that 6 and 7 exhibited significant cytotoxicities with IC50 values in the low micromolar range.

  DOI：

  10.1021/ol400694h

文献信息

• Isolation and Photoinduced Conversion of 6-<i>epi</i>-Stephacidins from <i>Aspergillus taichungensis</i>
  作者：Shengxin Cai、Yepeng Luan、Xianglan Kong、Tianjiao Zhu、Qianqun Gu、Dehai Li

  DOI：10.1021/ol400694h

  日期：2013.5.3

  Three prenylated indole alkaloids with a rare anti bicyclo-[2.2.2]diazaoctane core ring (5-7) were isolated from Aspergillus taichungensis. The structures including absolute configurations were elucidated based on NMR, X-ray, and CD methods. (+)-Versicolamides B and C (8-9) which contain a spiro-center, together with seven analogues (7, 10-15), were isolated as photoinduced conversion products of 6. Biological evaluation indicated that 6 and 7 exhibited significant cytotoxicities with IC50 values in the low micromolar range.