Lissoclin C

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: Lissoclin C
• 英文别名: 7-bromo-1-(1H-imidazol-5-ylmethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• 化学式: C₁₅H₁₅BrN₄
• 分子量: 331.215
• InChiKey: YEMKOGHBIUALJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  56.5
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(-)-1-苯乙基异氰酸酯 、 Lissoclin C 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 、
  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

文献信息

• Five new alkaloids from the tropical ascidian, Lissoclinum sp. lissoclinotoxin A is chiral
  作者：Philip A. Searle、Tadeusz F. Molinski

  DOI：10.1021/jo00101a018

  日期：1994.11

  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.