(6aR,9R,9aR)-9-乙酰基-5-氯-3-[(1E,3E,5S)-3,5-二甲基庚-1,3-二烯基]-6a-甲基-9,9a-二氢呋喃并[5,4-h]异苯并吡喃-6,8-二酮 | 154037-52-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (6aR,9R,9aR)-9-乙酰基-5-氯-3-[(1E,3E,5S)-3,5-二甲基庚-1,3-二烯基]-6a-甲基-9,9a-二氢呋喃并[5,4-h]异苯并吡喃-6,8-二酮
• 英文名称: (6aR,9R,9aR)-9-Acetyl-5-chloro-3-((1E,3E)-(S)-3,5-dimethyl-hepta-1,3-dienyl)-6a-methyl-9,9a-dihydro-6aH-furo[2,3-h]isochromene-6,8-dione
• 英文别名: Isochromophilone I；(6aR,9R,9aR)-9-acetyl-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-6a-methyl-9,9a-dihydrofuro[2,3-h]isochromene-6,8-dione
• CAS: 154037-52-2
• 化学式: C₂₃H₂₅ClO₅
• 分子量: 416.901
• InChiKey: BFKHRJFETIBYAU-WJKJBVSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6aR,9R,9aR)-9-乙酰基-5-氯-3-[(1E,3E,5S)-3,5-二甲基庚-1,3-二烯基]-6a-甲基-9,9a-二氢呋喃并[5,4-h]异苯并吡喃-6,8-二酮 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.67h， 生成 (6aR,9R,9aR)-9-Acetyl-5-chloro-3-((S)-3,5-dimethyl-heptyl)-6a-methyl-9,9a-dihydro-6aH-furo[2,3-h]isochromene-6,8-dione
  参考文献：
  名称：

  New Brominated and Halogen-less Derivatives and Structure-activity Relationship of Azaphilones Inhibiting gp120-CD4 Binding.

  摘要：

  Novel brominated and halogen-less azaphilone (oxoisochromane) derivatives, 5-bromoochrephilone and dechloroisochromophilone IV, and known derivatives, dechloroisochromophilone III and isorotiorin, were isolated from the culture broth of a producing organism of isochromophilones I and II (azaphilones inhibiting gp120-CD4 binding), Penicillium multicolor FO-2338, fermented in a medium containing potassium bromide. Nineteen azaphilone-related compounds isolated from the above strain and from other fungi were tested for the inhibition of gp120-CD4 binding and the structure-activity relationship is discussed. Consequently, 5-bromoochrephilone is the strongest inhibitor (IC50, 2.5 μM). A halogen atom at C-5, a proton at C-8 and a diene structure in C-3 side chain of 6-oxoisochromane ring are necessary for gp120-CD4 binding.

  DOI：

  10.7164/antibiotics.51.1004

文献信息

• New Brominated and Halogen-less Derivatives and Structure-activity Relationship of Azaphilones Inhibiting gp120-CD4 Binding.
  作者：KEIICHI MATSUZAKI、HARUMI TAHARA、JUNJI INOKOSHI、HARUO TANAKA、ROKURO MASUMA、SATOSHI OMURA

  DOI：10.7164/antibiotics.51.1004

  日期：——

  Novel brominated and halogen-less azaphilone (oxoisochromane) derivatives, 5-bromoochrephilone and dechloroisochromophilone IV, and known derivatives, dechloroisochromophilone III and isorotiorin, were isolated from the culture broth of a producing organism of isochromophilones I and II (azaphilones inhibiting gp120-CD4 binding), Penicillium multicolor FO-2338, fermented in a medium containing potassium bromide. Nineteen azaphilone-related compounds isolated from the above strain and from other fungi were tested for the inhibition of gp120-CD4 binding and the structure-activity relationship is discussed. Consequently, 5-bromoochrephilone is the strongest inhibitor (IC50, 2.5 μM). A halogen atom at C-5, a proton at C-8 and a diene structure in C-3 side chain of 6-oxoisochromane ring are necessary for gp120-CD4 binding.