andrographolide-14α-O-bromoacetate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: andrographolide-14α-O-bromoacetate
• 英文别名: [(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] 2-bromoacetate
• 化学式: C₂₂H₃₁BrO₆
• 分子量: 471.389
• InChiKey: YSHPDQWUFVHCLZ-FRCKFQSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  穿心莲内酯 在 吡啶 、 4-二甲氨基吡啶 、 水 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 丙酮 为溶剂， 反应 4.0h， 生成 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

文献信息

• Synthesis and biological evaluation of andrographolide analogues as anti-cancer agents
  作者：Ranjan Preet、Biswajit Chakraborty、Sumit Siddharth、Purusottam Mohapatra、Dipon Das、Shakti Ranjan Satapathy、Supriya Das、Nakul C. Maiti、Prakas R. Maulik、Chanakya Nath Kundu、Chinmay Chowdhury

  DOI：10.1016/j.ejmech.2014.07.088

  日期：2014.10

  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.