andrographolide-14α-O-phthalate | 1260159-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: andrographolide-14α-O-phthalate
• 英文别名: 2-[(3S,4E)-4-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-5-oxooxolan-3-yl]oxycarbonylbenzoic acid
• CAS: 1260159-28-1
• 化学式: C₂₈H₃₄O₈
• 分子量: 498.573
• InChiKey: PQMQHAQTJWXFPJ-RIFYKTRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  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

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.