3,19-isopropylideneandrographolide-14α-O-glutarate | 1260159-18-9

• 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: 3,19-isopropylideneandrographolide-14α-O-glutarate
• 英文别名: 5-[(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]oxy-5-oxopentanoic acid
• CAS: 1260159-18-9
• 化学式: C₂₈H₄₀O₈
• 分子量: 504.621
• InChiKey: XIAWRIREZAZTEC-YYPXVYMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  3,19-isopropylideneandrographolide-14α-O-glutarate 在 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 以86%的产率得到andrographolide-14α-O-glutarate
  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：

  穿心莲内酯 在 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 7.0h， 生成 3,19-isopropylideneandrographolide-14α-O-glutarate
  参考文献：
  名称：

  Identification of poly(ADP-ribose)polymerase 1 and 2 (PARP1/2) as targets of andrographolide using an integrated chemical biology approach

  摘要：

  安龙草素是第一个不含酰胺结构且在纳摩尔范围内具有抑制活性的PARP天然产物抑制剂。这种化学结构对于扩展PARP抑制剂的结构类型非常重要。

  DOI：

  10.1039/d1cc02272e

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.
• Identification of poly(ADP-ribose)polymerase 1 and 2 (PARP1/2) as targets of andrographolide using an integrated chemical biology approach
  作者：Wenchao Li、Bowen Pan、Yang Shi、Meiying Wang、Tianjiao Han、Qing Wang、Guifang Duan、Hongzheng Fu

  DOI：10.1039/d1cc02272e

  日期：——

  Andrographolide is the first PARP natural product inhibitor that does not contain an amide structure and has an inhibitory activity in the nanomolar range. This chemical structure is significant for expanding the structural type of PARP inhibitors.

  安龙草素是第一个不含酰胺结构且在纳摩尔范围内具有抑制活性的PARP天然产物抑制剂。这种化学结构对于扩展PARP抑制剂的结构类型非常重要。