(3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5,8a-dimethyl-2-methylene-5-[(trityl)methyl]decalin-1-yl]ethylene}-4-hydroxyoxolan-2-one | 352661-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5,8a-dimethyl-2-methylene-5-[(trityl)methyl]decalin-1-yl]ethylene}-4-hydroxyoxolan-2-one
• 英文别名: 19-Tr-andrographolide；19-O-Triphenylmethylandrographolide；(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5,8a-dimethyl-2-methylidene-5-(trityloxymethyl)-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
• CAS: 352661-68-8
• 化学式: C₃₉H₄₄O₅
• 分子量: 592.775
• InChiKey: YTLLOAKGAYAHHW-HHAQPBJMSA-N

物化性质

• 熔点：
  112-114 °C
• 沸点：
  727.2±60.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5,8a-dimethyl-2-methylene-5-[(trityl)methyl]decalin-1-yl]ethylene}-4-hydroxyoxolan-2-one 在 甲酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(1R,2R,4aR,5S,6S,8aS)-5-[(2E)-2-[(4S)-4-acetyloxy-2-oxooxolan-3-ylidene]ethyl]-1-(hydroxymethyl)-1,4a-dimethylspiro[3,4,5,7,8,8a-hexahydro-2H-naphthalene-6,2'-oxirane]-2-yl] acetate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of andrographolide analogues as novel cytotoxic agents

  摘要：

  Andrographolide 1, the cytotoxic agent of the plant Androgrophis paniculata was subjected to semi-synthetic studies leading to the preparation of a number of potent and novel analogues. Of the analogues synthesized, while 8,17-epoxy andrographolide 6 retained the cytotoxic activity of 1, ester derivatives of 6 exhibited considerable improvement in activity. Lower activity was observed when the epoxy moiety in the triacetate 9, derived from 6 was modified. Synthesis and structure-activity relationships are discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.090
• 作为产物：
  描述：

  三苯基氯甲烷 、 穿心莲内酯 在 吡啶 作用下， 反应 2.5h， 以99%的产率得到(3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5,8a-dimethyl-2-methylene-5-[(trityl)methyl]decalin-1-yl]ethylene}-4-hydroxyoxolan-2-one
  参考文献：
  名称：

  具有强细胞毒活性的新的取代的C-19-穿心莲内酯类似物

  摘要：

  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。

  DOI：

  10.1016/j.bmcl.2011.11.085

文献信息

• One-pot three steps cascade synthesis of novel isoandrographolide analogues and their cytotoxic activity
  作者：Teerapich Kasemsuk、Pawinee Piyachaturawat、Rada Bunthawong、Uthaiwan Sirion、Kanoknetr Suksen、Apichart Suksamrarn、Rungnapha Saeeng

  DOI：10.1016/j.ejmech.2017.07.035

  日期：2017.9

  andrographolide analogues is reported from a naturally occurring and abundant andrographolide isolated from aerial parts of Andrographis paniculata. Reactions in the one-pot proceed through a cascade epoxide ring opening by aniline derivatives/intramolecular ring closing and oxa-conjugate addition-elimination reactions. This methodology produces a new series of 17-amino-8-epi-isoandrographolide analogues in fair

  新颖穿心莲内酯类似物的有效一锅法合成是从的地上部分分离的天然存在的和丰富的穿心莲内酯报道穿心莲。一锅中的反应通过苯胺衍生物/分子内的闭环和氧杂-共轭加成-消除反应通过级联的环氧开环进行。该方法使用经济和环境方法，在室温下无需碱或催化剂的情况下，以高立体选择性公平，优异地产生了一系列新的17-氨基-8-表位异二十碳内酯类似物。获得了二十五个类似物，并针对六种癌细胞系评估了所有新类似物的细胞毒性，以寻找基于穿心莲内酯结构的新的先导化合物。
• CN116898841
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and structure–activity relationships of andrographolide analogues as novel cytotoxic agents
  作者：Srinivas Nanduri、Vijay Kumar Nyavanandi、Siva Sanjeeva Rao Thunuguntla、Sridevi Kasu、Mahesh Kumar Pallerla、P. Sai Ram、Sriram Rajagopal、R. Ajaya Kumar、Rajagopalan Ramanujam、J. Moses Babu、Krishnamurthi Vyas、A. Sivalakshmi Devi、G. Om Reddy、Venkateswarlu Akella

  DOI：10.1016/j.bmcl.2004.06.090

  日期：2004.9

  Andrographolide 1, the cytotoxic agent of the plant Androgrophis paniculata was subjected to semi-synthetic studies leading to the preparation of a number of potent and novel analogues. Of the analogues synthesized, while 8,17-epoxy andrographolide 6 retained the cytotoxic activity of 1, ester derivatives of 6 exhibited considerable improvement in activity. Lower activity was observed when the epoxy moiety in the triacetate 9, derived from 6 was modified. Synthesis and structure-activity relationships are discussed. (C) 2004 Elsevier Ltd. All rights reserved.
• 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。