Lissoclin A

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: Lissoclin A
• 英文别名: 3-methyl-N-[2-(11-methylsulfanyl-12-oxo-8,14-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,8,10,13,15-octaen-10-yl)ethyl]butanamide
• 化学式: C₂₃H₂₃N₃O₂S
• 分子量: 405.521
• InChiKey: CYSORIPWPDCIMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  97.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Lissoclin A 以 甲醇 为溶剂， 反应 3.0h， 生成 3-Methyl-N-[2-(8H-4-oxa-6-thia-3,8-diaza-benzo[de]cyclopenta[b]anthracen-7-yl)-ethyl]-butyramide
  参考文献：
  名称：

  Five new alkaloids from the tropical ascidian, Lissoclinum sp. lissoclinotoxin A is chiral

  摘要：

  Five new alkaloids, lissoclin A (1), lissoclin B (2), Lissoclin C (3), lissoclinotoxin C (5), and the dimeric lissoclinotoxin D (6), were isolated along with the known compounds lissoclinotoxin A (4), 2-phenylethylamine (11), and 6-bromotryptamine (12) from Lissoclinum sp. collected from the Great Barrier Reef, Australia. Lissoclin A (1) undergoes photorearrangement to a new benzo-l,and oxathiazoline 10. The C-13 NMR spectrum of 4 is reported for the first time and the structure independently assigned by conversion to the known varacin N-trinuoroacetamide with diazomethane and [C-13]diazomethane. Compound 4 is chiral and exhibits unusual stereoisomerism due to restricted inversion about the benzopentathiepin ring. Lissoclinotoxin A (4) and D (6) exhibit antifungal activity against Candida albicans.

  DOI：

  10.1021/jo00101a018