chaetomugilin I | 1187848-00-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: chaetomugilin I
• 英文别名: (7S,8S)-5-chloro-7-hydroxy-3-[(E,3R,4R)-4-hydroxy-3-methylpent-1-enyl]-7-methyl-8-[(E)-3-methyl-2-oxopent-3-enyl]-8H-isochromen-6-one
• CAS: 1187848-00-5
• 化学式: C₂₂H₂₇ClO₅
• 分子量: 406.906
• InChiKey: BYFBAJVBSPNIFS-YJTDBNEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  chaetomugilin I 在 potassium hydroxide 、 硫酸 作用下， 以 水 为溶剂， 反应 3.0h， 以0.5 mg的产率得到(2E,4R,5R)-5-hydroxy-4-methylhex-2-enoic acid
  参考文献：
  名称：

  New class azaphilone produced by a marine fish-derived Chaetomium globosum. The stereochemistry and biological activities

  摘要：

  Four new metabolites, chaetomugilins P-R and 11-epi-chaetomugilin I, were isolated from a strain of Chaetomium globosum originally obtained from the marine fish Mugil cephalus, and their absolute stereo-structures were elucidated on the basis of spectroscopic analyses, including 1D and 2D NMR techniques and various chemical transformations. Particularly, the skeleton of chaetomugilin P is different from that of other azaphilones isolated from this fungal strain to date. In addition, these compounds significantly inhibited the growth of cultured P388, HL-60, L1210 and KB cell lines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.008
• 作为产物：
  描述：

  chaetomugilin K 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以59.1%的产率得到chaetomugilin I
  参考文献：
  名称：

  Chaetomugilins I–O, new potent cytotoxic metabolites from a marine-fish-derived Chaetomium species. Stereochemistry and biological activities

  摘要：

  Chaetomugilins I-O were isolated from a strain of Chaetomium globosum originally isolated from the marine fish Mugil cephalus, and their absolute stereostructures were elucidated on the basis of spectroscopic analyses, including 1D and 2D NMR techniques, as well as chemical transformations. These compounds exhibited significant growth inhibition of cultured P388, HL-60, L1210, and KB cell lines. In addition, chaetomugilin I showed selective cytotoxic activity against 39 human cancer cell lines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.125