Lissoclinotoxin 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: Lissoclinotoxin A
• 英文别名: 9-(2-Aminoethyl)-6-methoxy-1,2,3,4,5-benzopentathiepin-7-ol
• 化学式: C₉H₁₁NO₂S₅
• 分子量: 325.522
• InChiKey: WQAHCFFHBFQTRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  182
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Lissoclinotoxin A 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 6,7-Dimethoxy-9-<2-ethyl>benzopentathiepin
  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

• Lissoclinotoxins: Antibiotic polysulfur derivatives from the tunicate Lissoclinum perforatum. Revised structure of lissoclinotoxin A
  作者：Marc Litaudon、François Trigalo、Marie-Thérése Martin、François Frappier、Michéle Guyot

  DOI：10.1016/s0040-4020(01)80690-6

  日期：1994.5

  Lissoclinotoxin B, a new pentathiepin derivative, was isolated from the tonicate Lissoclinum perforatum. Structure elucidation of this compound is described based on spectroscopic data, together with a revised structure for lissoclinotoxin A. A synthesis of tetraacetyl isolissoclinotoxin A is described.
• 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.