3,19-isopropylideneandrographolide-14α-O-bromoacetate

• 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-bromoacetate
• 英文别名: [(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] 2-bromoacetate
• 化学式: C₂₅H₃₅BrO₆
• 分子量: 511.453
• InChiKey: USPHUURADYNSNW-JZHKGMGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,19-isopropylideneandrographolide-14α-O-bromoacetate 在 水 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以70%的产率得到andrographolide-14α-O-bromoacetate
  参考文献：
  名称：

  Synthesis and biological evaluation of andrographolide analogues as anti-cancer agents

  摘要：

  A new family of andrographolide analogues were synthesized and screened in vitro against kidney (HEK-293) and breast (MCF-7) cancer cells. The anti-cancer effects of the active analogues (2b, 2c and 4c) were determined by multiple cell based assays such as MTT, immunostaining, FACS, western blotting and transcriptional inhibition of NF-kappa B activity. Importantly, these compounds were found to possess higher anti-cancer potency than andrographolide and low toxicity to normal (VERO and MCF-10A) cells. Increased level of Bax/Bcl-xL ratio, caspase 3, and sub C1 population, higher expression level of tumor suppressor protein p53 and lower expression level of NF-kappa B suggested potent apoptotic property of the active analogues. Data revealed that the andrographolide derivative-mediated cell death in cancer cells was p53 dependent (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.088
• 作为产物：
  描述：

  穿心莲内酯 在 吡啶 、 4-二甲氨基吡啶 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 3.5h， 生成 3,19-isopropylideneandrographolide-14α-O-bromoacetate
  参考文献：
  名称：

  Synthesis and biological evaluation of andrographolide analogues as anti-cancer agents

  摘要：

  A new family of andrographolide analogues were synthesized and screened in vitro against kidney (HEK-293) and breast (MCF-7) cancer cells. The anti-cancer effects of the active analogues (2b, 2c and 4c) were determined by multiple cell based assays such as MTT, immunostaining, FACS, western blotting and transcriptional inhibition of NF-kappa B activity. Importantly, these compounds were found to possess higher anti-cancer potency than andrographolide and low toxicity to normal (VERO and MCF-10A) cells. Increased level of Bax/Bcl-xL ratio, caspase 3, and sub C1 population, higher expression level of tumor suppressor protein p53 and lower expression level of NF-kappa B suggested potent apoptotic property of the active analogues. Data revealed that the andrographolide derivative-mediated cell death in cancer cells was p53 dependent (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.07.088