verticillin A

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: verticillin A
• 英文别名: (1S,2S,11R,14S)-2-hydroxy-3-[(1S,2S,3S,11R,14S)-2-hydroxy-14,18-dimethyl-13,17-dioxo-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-trien-3-yl]-14,18-dimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.01,12.03,11.04,9]octadeca-4,6,8-triene-13,17-dione
• 化学式: C₃₀H₂₈N₆O₆S₄
• 分子量: 696.853
• InChiKey: IMGTYEJTVRXGLW-LTEJGUQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  46
• 可旋转键数：
  1
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  247
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  verticillin A 在 三苯基膦 作用下， 以 氯仿 为溶剂， 反应 5.0h， 生成 gliocladine C
  参考文献：
  名称：

  Nematicidal Epipolysulfanyldioxopiperazines from Gliocladium roseum

  摘要：

  Five new verticillin-type epipolysulfanyldioxopiperazines, gliocladine A (1), B (2), C (3), D (4), and E (5), were isolated from wheat solid-substrate fermentation of Gliocladium roseum 1A, along with four known compounds, verticillin A (6), 11'-deoxyverticillin A (7), Sch52900 (8), and Sch52901 (9). Their structures were elucidated by extensive 1D and 2D NMR studies, MS, and chemical transformations. In vitro immersion tests showed that all nine compounds exhibited antinematodal activity against Caenorhabditis elegans and Panagrellus redivivus. The monomeric epipolysulfanydioxopiperazines (3-5), with the indole moiety, were found to be less active than the dimeric compounds (1, 2, 6-8).

  DOI：

  10.1021/np0502241
• 作为产物：
  描述：

  gliocladine A 在 三苯基膦 作用下， 以 氯仿 为溶剂， 反应 1.5h， 以11 mg的产率得到verticillin A
  参考文献：
  名称：

  Nematicidal Epipolysulfanyldioxopiperazines from Gliocladium roseum

  摘要：

  Five new verticillin-type epipolysulfanyldioxopiperazines, gliocladine A (1), B (2), C (3), D (4), and E (5), were isolated from wheat solid-substrate fermentation of Gliocladium roseum 1A, along with four known compounds, verticillin A (6), 11'-deoxyverticillin A (7), Sch52900 (8), and Sch52901 (9). Their structures were elucidated by extensive 1D and 2D NMR studies, MS, and chemical transformations. In vitro immersion tests showed that all nine compounds exhibited antinematodal activity against Caenorhabditis elegans and Panagrellus redivivus. The monomeric epipolysulfanydioxopiperazines (3-5), with the indole moiety, were found to be less active than the dimeric compounds (1, 2, 6-8).

  DOI：

  10.1021/np0502241

文献信息

• Nematicidal Epipolysulfanyldioxopiperazines from <i>Gliocladium </i><i>r</i><i>oseum</i>
  作者：Jin-Yan Dong、Hong-Ping He、Yue-Mao Shen、Ke-Qin Zhang

  DOI：10.1021/np0502241

  日期：2005.10.1

  Five new verticillin-type epipolysulfanyldioxopiperazines, gliocladine A (1), B (2), C (3), D (4), and E (5), were isolated from wheat solid-substrate fermentation of Gliocladium roseum 1A, along with four known compounds, verticillin A (6), 11'-deoxyverticillin A (7), Sch52900 (8), and Sch52901 (9). Their structures were elucidated by extensive 1D and 2D NMR studies, MS, and chemical transformations. In vitro immersion tests showed that all nine compounds exhibited antinematodal activity against Caenorhabditis elegans and Panagrellus redivivus. The monomeric epipolysulfanydioxopiperazines (3-5), with the indole moiety, were found to be less active than the dimeric compounds (1, 2, 6-8).