varacin A

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: varacin A
• 英文别名: 2-(4,5-dimethoxy-1,2,3-benzotrithiol-7-yl)ethanamine
• 化学式: C₁₀H₁₃NO₂S₃
• 分子量: 275.417
• InChiKey: UNCWRRPZMNUQDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-溴香兰素 在 吡啶 、 喹啉 、 二氯化二硫 、 lithium aluminium tetrahydride 、 ammonium acetate 、 氨 、 溴 、 sodium 、 四丁基碘化铵 、 potassium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 溶剂黄146 为溶剂， 生成 varacin A
  参考文献：
  名称：

  Synthesis of varacin, a cytotoxic naturally occurring benzopentathiepin isolated from a marine ascidian

  摘要：

  The total synthesis of varacin (1), a cytotoxic metabolite isolated from a marine ascidian, has been accomplished in 11 steps from vanillin, providing unambiguous confirmation of the unique dopamine-related benzopentathiepin structure.

  DOI：

  10.1021/jo00069a006

文献信息

• Isodiplamine, cystodytin K and lissoclinidine: novel bioactive alkaloids from the New Zealand ascidian Lissoclinum notti
  作者：David R Appleton、A.Norrie Pearce、Gretchen Lambert、Russell C Babcock、Brent R Copp

  DOI：10.1016/s0040-4020(02)01296-6

  日期：2002.12

  A study of the bioactive crude extract of the New Zealand ascidian Lissoclinum notti led to the isolation of the new pyridoacridine alkaloids isodiplamine (4), cystodytin K (5) and lissoclinidine (6), as well as the known pyridoacridine alkaloids diplamine (7) and cystodytin J (8) and the benzopentathiepin varacin (3) and related trithiane varacin A. The new alkaloids were characterised using standard spectroscopic techniques, including 2D H-1-N-15 NMR experiments. Pyridoacridine alkaloids 4-8 were assayed for a range of biological activities including antitumour and antibiotic properties. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of varacin, a cytotoxic naturally occurring benzopentathiepin isolated from a marine ascidian
  作者：Paul W. Ford、Bradley S. Davidson

  DOI：10.1021/jo00069a006

  日期：1993.8

  The total synthesis of varacin (1), a cytotoxic metabolite isolated from a marine ascidian, has been accomplished in 11 steps from vanillin, providing unambiguous confirmation of the unique dopamine-related benzopentathiepin structure.