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

• 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-chloroacetate
• 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-chloroacetate
• 化学式: C₂₅H₃₅ClO₆
• 分子量: 467.002
• InChiKey: JNVLKAKJCGDWDX-JZHKGMGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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-chloroacetate 在 溶剂黄146 、 potassium iodide 作用下， 以 水 、 丙酮 为溶剂， 反应 18.33h， 生成
  参考文献：
  名称：

  一类阿司匹林衍生物及其制法和应用

  摘要：

  本发明公开了一类具有式I或式II所示结构的乙酰水杨酸衍生物或其异构体、前药、药学上可接受的盐、复盐、溶剂化物及其在制备抑制乙酰肝素酶的制剂中的应用。本发明还公开了乙酰水杨酸衍生物的制备方法。本发明化合物能显著抑制乙酰肝素酶的活性，对各种肿瘤细胞具有非常强的抑制活性，可用于制备抗肿瘤的药物。本发明化合物制备方法简单，操作简便，所得化合物纯度好、收率高。

  公开号：

  CN108129468B
• 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-chloroacetate
  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

• 一类阿司匹林衍生物及其制法和应用
  申请人：四川理工学院

  公开号：CN108129468B

  公开（公告）日：2020-09-29

  本发明公开了一类具有式I或式II所示结构的乙酰水杨酸衍生物或其异构体、前药、药学上可接受的盐、复盐、溶剂化物及其在制备抑制乙酰肝素酶的制剂中的应用。本发明还公开了乙酰水杨酸衍生物的制备方法。本发明化合物能显著抑制乙酰肝素酶的活性，对各种肿瘤细胞具有非常强的抑制活性，可用于制备抗肿瘤的药物。本发明化合物制备方法简单，操作简便，所得化合物纯度好、收率高。
• 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.