(4R,4aR,8aS)-3-[(1R,4aS,8aR)-1-[(E)-2-(furan-3-yl)ethenyl]-2,5,5,8a-tetramethyl-4-oxo-1,3,4a,6,7,8-hexahydronaphthalen-2-yl]-4-[(E)-2-(furan-3-yl)ethenyl]-3,4a,8,8-tetramethyl-2,4,5,6,7,8a-hexahydronaphthalen-1-one | 1228147-55-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4R,4aR,8aS)-3-[(1R,4aS,8aR)-1-[(E)-2-(furan-3-yl)ethenyl]-2,5,5,8a-tetramethyl-4-oxo-1,3,4a,6,7,8-hexahydronaphthalen-2-yl]-4-[(E)-2-(furan-3-yl)ethenyl]-3,4a,8,8-tetramethyl-2,4,5,6,7,8a-hexahydronaphthalen-1-one
• CAS: 1228147-55-4
• 化学式: C₄₀H₅₄O₄
• 分子量: 598.866
• InChiKey: UXOFKXZYXQTXFQ-YXVOMAJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  44
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4S,4aR,8aS)-4-((E)-2-(furan-3-yl)vinyl)-3,4a,8,8-tetramethyl-4a,5,6,7,8,8a-hexa hydronaphthalen-(4H)-one 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以40%的产率得到(4R,4aR,8aS)-3-[(1R,4aS,8aR)-1-[(E)-2-(furan-3-yl)ethenyl]-2,5,5,8a-tetramethyl-4-oxo-1,3,4a,6,7,8-hexahydronaphthalen-2-yl]-4-[(E)-2-(furan-3-yl)ethenyl]-3,4a,8,8-tetramethyl-2,4,5,6,7,8a-hexahydronaphthalen-1-one
  参考文献：
  名称：

  Synthesis, cytotoxic activity and structure–activity relationships of hedychenone analogues

  摘要：

  Hedychenone, a plant-derived labdane diterpenoid, showed potent in vitro cytotoxic activity against cancerous cells. In the present study, a series of analogues have been synthesized by modi. cation of the furanoid ring, double bond and the vinylic methyl functionality of this natural product lead and evaluated for their cytotoxic activities against human cancer cell lines. The structures of the target compounds were established by IR, H-1 NMR and mass spectral analysis. Majority of the analogues displayed potent activity than the parent compound, hedychenone. Preliminary structure-activity relationship studies indicated that furanoid ring has a greater impact on cytotoxicity than that of the decalone nucleus. However, dimerization through C-8 significantly enhanced the cytotoxic activity of the hedychenone. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.101

文献信息

• Synthesis, cytotoxic activity and structure–activity relationships of hedychenone analogues
  作者：P. Prabhakar Reddy、Aditya G. Lavekar、K. Suresh Babu、R. Ranga Rao、J. Shashidhar、G. Shashikiran、J. Madhusudana Rao

  DOI：10.1016/j.bmcl.2010.02.101

  日期：2010.4

  Hedychenone, a plant-derived labdane diterpenoid, showed potent in vitro cytotoxic activity against cancerous cells. In the present study, a series of analogues have been synthesized by modi. cation of the furanoid ring, double bond and the vinylic methyl functionality of this natural product lead and evaluated for their cytotoxic activities against human cancer cell lines. The structures of the target compounds were established by IR, H-1 NMR and mass spectral analysis. Majority of the analogues displayed potent activity than the parent compound, hedychenone. Preliminary structure-activity relationship studies indicated that furanoid ring has a greater impact on cytotoxicity than that of the decalone nucleus. However, dimerization through C-8 significantly enhanced the cytotoxic activity of the hedychenone. (C) 2010 Elsevier Ltd. All rights reserved.