rotiorinol A | 901309-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: rotiorinol A
• 英文别名: 6-acetyl-3-(3,5-dimethyl-1E,3E-heptadienyl)-9R-hydroxy-8a(R)-methyl-7H-furo[2,3-g]-2-benzopyran-7-one；(9R,9aR)-3-acetyl-6-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-9-hydroxy-9a-methyl-9H-furo[3,2-g]isochromen-2-one
• CAS: 901309-41-9
• 化学式: C₂₃H₂₆O₅
• 分子量: 382.456
• InChiKey: QXVIQXFZWZQGMX-CBNFSBMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  rotiorinol A 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以49.3%的产率得到(-)-rotiorin
  参考文献：
  名称：

  Antifungal Azaphilones from the Fungus Chaetomium cupreum CC3003

  摘要：

  Three new azaphilones named rotiorinols A-C (1-3), two new stereoisomers, (-)-rotiorin (4) and epi-isochromophilone II (5), and a known compound, rubrorotiorin (6), were isolated from the fungus Chaetomium cupreum CC3003. Structures were established on the basis of spectroscopic evidence. The absolute configuration of 1 was determined by the modified Mosher's method along with an X-ray analysis of its acetate derivative, as well as by chemical transformation. Compounds 1, 3, 4, and 6 exhibited antifungal activity against Candida albicans with IC50 values of 10.5, 16.7, 24.3, and 0.6 mu g/mL, respectively.

  DOI：

  10.1021/np060051v

文献信息

• Antifungal Azaphilones from the Fungus <i>Chaetomium </i><i>c</i><i>upreum</i> CC3003
  作者：Somdej Kanokmedhakul、Kwanjai Kanokmedhakul、Pitak Nasomjai、Sysavad Louangsysouphanh、Kasem Soytong、Minoru Isobe、Palangpon Kongsaeree、Samran Prabpai、Apichart Suksamrarn

  DOI：10.1021/np060051v

  日期：2006.6.1

  Three new azaphilones named rotiorinols A-C (1-3), two new stereoisomers, (-)-rotiorin (4) and epi-isochromophilone II (5), and a known compound, rubrorotiorin (6), were isolated from the fungus Chaetomium cupreum CC3003. Structures were established on the basis of spectroscopic evidence. The absolute configuration of 1 was determined by the modified Mosher's method along with an X-ray analysis of its acetate derivative, as well as by chemical transformation. Compounds 1, 3, 4, and 6 exhibited antifungal activity against Candida albicans with IC50 values of 10.5, 16.7, 24.3, and 0.6 mu g/mL, respectively.