2-[(3S,4E)-4-[2-[(4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylidene-1,4a,5,6,7,9,10,10a-octahydronaphtho[2,1-d][1,3]dioxin-7-yl]ethylidene]-5-oxooxolan-3-yl]oxycarbonylbenzoic acid | 1260159-20-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 2-[(3S,4E)-4-[2-[(4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylidene-1,4a,5,6,7,9,10,10a-octahydronaphtho[2,1-d][1,3]dioxin-7-yl]ethylidene]-5-oxooxolan-3-yl]oxycarbonylbenzoic acid
• CAS: 1260159-20-3
• 化学式: C₃₁H₃₈O₈
• 分子量: 538.638
• InChiKey: GNHROKGZUWGVQB-PIABWBDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[(3S,4E)-4-[2-[(4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylidene-1,4a,5,6,7,9,10,10a-octahydronaphtho[2,1-d][1,3]dioxin-7-yl]ethylidene]-5-oxooxolan-3-yl]oxycarbonylbenzoic acid 在 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 以88%的产率得到andrographolide-14α-O-phthalate
  参考文献：
  名称：

  Synthesis, cytotoxicity, and structure–activity relationship (SAR) studies of andrographolide analogues as anti-cancer agent

  摘要：

  A series of analogues of andrographolide, prepared through chemo-selective functionalization at C14 hydroxy, have been evaluated for in vitro cytotoxicities against human leukemic cell lines. Two of the analogues (6a, 9b) exhibited significant potency. Preliminary studies on structure-activity relationship (SAR) revealed that the alpha-alkylidene-gamma-butyrolactone moiety of andrographolide played a major role in the activity profile. The structures of the analogues were established through spectroscopic and analytical data (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.126
• 作为产物：
  描述：

  苯酐 、 3,18-O-isopropylideneandrographolide 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以41%的产率得到2-[(3S,4E)-4-[2-[(4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylidene-1,4a,5,6,7,9,10,10a-octahydronaphtho[2,1-d][1,3]dioxin-7-yl]ethylidene]-5-oxooxolan-3-yl]oxycarbonylbenzoic acid
  参考文献：
  名称：

  Synthesis, cytotoxicity, and structure–activity relationship (SAR) studies of andrographolide analogues as anti-cancer agent

  摘要：

  A series of analogues of andrographolide, prepared through chemo-selective functionalization at C14 hydroxy, have been evaluated for in vitro cytotoxicities against human leukemic cell lines. Two of the analogues (6a, 9b) exhibited significant potency. Preliminary studies on structure-activity relationship (SAR) revealed that the alpha-alkylidene-gamma-butyrolactone moiety of andrographolide played a major role in the activity profile. The structures of the analogues were established through spectroscopic and analytical data (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.126

文献信息

• Synthesis, cytotoxicity, and structure–activity relationship (SAR) studies of andrographolide analogues as anti-cancer agent
  作者：Bimolendu Das、Chinmay Chowdhury、Deepak Kumar、Rupashree Sen、Rajneeta Roy、Padma Das、Mitali Chatterjee

  DOI：10.1016/j.bmcl.2010.09.126

  日期：2010.12

  A series of analogues of andrographolide, prepared through chemo-selective functionalization at C14 hydroxy, have been evaluated for in vitro cytotoxicities against human leukemic cell lines. Two of the analogues (6a, 9b) exhibited significant potency. Preliminary studies on structure-activity relationship (SAR) revealed that the alpha-alkylidene-gamma-butyrolactone moiety of andrographolide played a major role in the activity profile. The structures of the analogues were established through spectroscopic and analytical data (C) 2010 Elsevier Ltd. All rights reserved.