14α-acetoxy-19-tert-butyldimethylsilyloxy-andrographolide | 1355018-51-7

• 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: 14α-acetoxy-19-tert-butyldimethylsilyloxy-andrographolide
• 英文别名: 19-TBS-14-Ac-andrographolide；[(3S,4E)-4-[2-[(1R,4aS,5R,6R,8aS)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-hydroxy-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-5-oxooxolan-3-yl] acetate
• CAS: 1355018-51-7
• 化学式: C₂₈H₄₆O₆Si
• 分子量: 506.755
• InChiKey: VJSLAEHMOUSVLS-MWTXHCMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.56
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  14α-acetoxy-19-tert-butyldimethylsilyloxy-andrographolide 在 戴斯-马丁氧化剂 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 3-oxo-14α-acetoxy-andrographolide
  参考文献：
  名称：

  SAR studies of 3,14,19-derivatives of andrographolide on anti-proliferative activity to cancer cells and toxicity to zebrafish: an in vitro and in vivo study

  摘要：

  安龙草素具有有趣的药效团，并吸引了许多研究对安龙草素衍生物的设计和合成进行研究。

  DOI：

  10.1039/c5ra00090d
• 作为产物：
  描述：

  14-O-acetyl-3,18-O-isopropylideneandrographolide 在 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 14α-acetoxy-19-tert-butyldimethylsilyloxy-andrographolide
  参考文献：
  名称：

  SAR studies of 3,14,19-derivatives of andrographolide on anti-proliferative activity to cancer cells and toxicity to zebrafish: an in vitro and in vivo study

  摘要：

  安龙草素具有有趣的药效团，并吸引了许多研究对安龙草素衍生物的设计和合成进行研究。

  DOI：

  10.1039/c5ra00090d

文献信息

• New substituted C-19-andrographolide analogues with potent cytotoxic activities
  作者：Uthaiwan Sirion、Sakkasem Kasemsook、Kanoknetr Suksen、Pawinee Piyachaturawat、Apichart Suksamrarn、Rungnapha Saeeng

  DOI：10.1016/j.bmcl.2011.11.085

  日期：2012.1

  structure–activity relationships (SARs) of 19 andrographolide analogues which were synthesized by modification at the three hydroxyl groups. A number of the andrographolide analogues showed much higher cytotoxic activities than that of the parent compound on cancer cells including P-388, KB, COL-2, MCF-7, LU-1 and ASK cells. SAR studies of the synthetic analogues indicated that the introduction of silyl ether or

  穿心莲内酯是穿心莲的主要二萜类内酯，对癌细胞有毒性。在本研究中，我们研究了19种穿心莲内酯类似物的结构-活性关系（SAR），它们通过在三个羟基上的修饰合成。许多穿心莲内酯类似物对癌细胞的细胞毒性活性比母体化合物高得多，包括P-388，KB，COL-2，MCF-7，LU-1和ASK细胞。合成类似物的SAR研究表明，将甲硅烷基醚或三苯基甲基醚基团引入母体化合物的C-19中会导致对癌细胞的毒性增加。19- O-三苯甲基醚类似物18 与有效的抗癌药玫瑰树碱相比，它显示出更高的细胞毒活性，该类似物可能是潜在的潜在结构导致开发新的抗癌药。
• Andrographolide derivative as STAT3 inhibitor that protects acute liver damage in mice
  作者：Shao-Ru Chen、Feng Li、Mo-Yu Ding、Decai Wang、Qi Zhao、Yitao Wang、Guo-Chun Zhou、Ying Wang

  DOI：10.1016/j.bmc.2018.09.002

  日期：2018.10

  Sustained activation of the Janus kinase-signal transducers and activators of transcription (JAK-STAT) pathway contributed to the progression of cancer and liver diseases. STAT3 signaling inhibitor has been extensively investigated for pharmacological use. We synthesized a series of andrographolide derivatives, and characterized their activity against STAT3 signaling pathway both in vitro and in the CCl4-induced acute liver damage mice model. Among these derivatives, compound 24 effectively inhibited phosphorylation and dimerization of STAT3 but not its DNA binding activity. Compound 24 significantly ameliorated carbon tetrachloride-induced acute liver damage in vivo without changing mice body weight. Treatment with 24 attenuated hepatic pathologic damage and promoted hepatic proliferation and activation of STAT3. Compound 24 inhibited elevated expression of alpha-smooth muscle actin and serum pro-inflammatory cytokines downstream of STAT3 but not those factors that are regulated by NF-kappa B or SMADs. In summary, our results suggest that compound 24 may serve as a potential therapeutic agent for the treatment of hepatic damage or a liver protection agent via regulating STAT3 activation.
• SAR studies of 3,14,19-derivatives of andrographolide on anti-proliferative activity to cancer cells and toxicity to zebrafish: an in vitro and in vivo study
  作者：Yuran Peng、Jingjing Li、Yicheng Sun、Judy Yuet-Wa Chan、Dekuan Sheng、Kun Wang、Ping Wei、Pingkai Ouyang、Decai Wang、Simon Ming Yuen Lee、Guo-Chun Zhou

  DOI：10.1039/c5ra00090d

  日期：——

  Andrographolide is bestowed with an interesting pharmacophore and has attracted numerous studies on the design and synthesis of andrographolide derivatives.

  安龙草素具有有趣的药效团，并吸引了许多研究对安龙草素衍生物的设计和合成进行研究。