14α,19-diacetoxy-andrographolide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 14α,19-diacetoxy-andrographolide
• 英文别名: andrographolide 14,19-diacetate；14,19-Ac-andrographolide；[(1R,2R,4aS,5R,8aS)-5-[(2E)-2-[(4S)-4-acetyloxy-2-oxooxolan-3-ylidene]ethyl]-2-hydroxy-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl acetate
• 化学式: C₂₄H₃₄O₇
• 分子量: 434.53
• InChiKey: FXWSJCKWCWNEON-IZQYNGGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  14α,19-diacetoxy-andrographolide 在 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 3-dehydroandrographolide
  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 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 14α,19-diacetoxy-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。
• Mild and selective deprotection method of acetylated steroids and diterpenes by dibutyltin oxide
  作者：Shao-Min Wang、Yan-Bing Zhang、Hong-Min Liu、Guo-Bin Yu、Ke-Rang Wang

  DOI：10.1016/j.steroids.2006.10.004

  日期：2007.1

  Dibutyltin oxide (DBTO) was first utilized for the deacetylation of steroid and diterpene esters. The results showed the deprotection of acetylated steroids and diterpenes separately with moderate catalysis dibutyltin oxide in methanol selectively removed part acetyl groups of these substrates, whereas several functional groups of the steroids and diterpenes were retained and neither isomerization nor degradation of these substrates was observed. It seems that the acetyl groups with lower steric hindrance or near carbonyl, alkoxy, or hydroxyl groups can be cleaved by the reaction, whereas the acetyl groups with higher steric hindrance or without carbonyl, alkoxy, or hydroxyl groups neighboring were retained under the same conditions. One of the interesting results obtained was the selective hydrolysis of the 3 beta-O-acetyl group in the presence of the 6 beta group in 3 beta,6 beta-Di-O-acetyl-5 alpha-hydroxypregn-16-en-20-one. This allows for subsequent introduction of one unit at C-3 and the other unit at C-6. This procedure is useful for the synthesis of a series of closely related isomers of 3 beta, 5 alpha, 6 beta-trihydroxypregn-16-en-20-one and other widespread polyhydroxysteroids in marine organisms and some terrestrial species. (c) 2006 Elsevier Inc. All rights reserved.
• 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。