latrunculol A | 1073607-02-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: latrunculol A
• 英文别名: (4R)-4-[(1R,4Z,8S,9S,10Z,12S,15R,17R)-8,9,17-trihydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,10-dien-17-yl]-1,3-thiazolidin-2-one
• CAS: 1073607-02-9
• 化学式: C₂₂H₃₃NO₇S
• 分子量: 455.573
• InChiKey: JIGPCDTWTJZFFF-HKBWBMOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  31
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  latrunculol A 、 2,2-二甲氧基丙烷 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 latrunculol A acetonide
  参考文献：
  名称：

  WO2010/14240

  摘要：

  公开号：

文献信息

• Interrogating the Bioactive Pharmacophore of the Latrunculin Chemotype by Investigating the Metabolites of Two Taxonomically Unrelated Sponges
  作者：Taro Amagata、Tyler A. Johnson、Robert H. Cichewicz、Karen Tenney、Susan L. Mooberry、Joseph Media、Matthew Edelstein、Frederick A. Valeriote、Phillip Crews

  DOI：10.1021/jm8008585

  日期：2008.11.27

  This study involved a campaign to isolate and study additional latrunculin analogues from two taxonomically unrelated sponges, Cacospongia mycoffiensis and Negombata magnifica. A total of 13 latrunculin analogues were obtained by four different ways, reisolation (1-4), our repository (5, 6), new derivatives (7-12), and a synthetic analogue (7a). The structures of the new metabolites were elucidated on the basis of a combination of comprehensive 1D and 2D NMR analysis, application of DFT calculations, and the preparation of acetonide derivative 7a. The cytotoxicities against both murine and human cancer cell lines observed for 1, 2, 7, 7a, 8, 9, and 12 were significant, and the IC50 range was 0.5-10 mu M. Among the cytotoxic derivatives, compound 9 did not exhibit microfilament-disrupting activity at 5 mu M. The implications of this observation and the value of further therapeutic study on key latrunculin derivatives are discussed.