3-oxo-23-nor-lup-20(29)-en-28-oic acid

• 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-oxo-23-nor-lup-20(29)-en-28-oic acid
• 英文别名: (1R,3aS,5aR,5bR,7aS,8R,11aS,11bR,13aR,13bR)-5a,5b,8,11a-tetramethyl-9-oxo-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,8,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• 化学式: C₂₉H₄₄O₃
• 分子量: 440.667
• InChiKey: DDKJFMDTDYNUQT-SKZKHSSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-oxo-23-nor-lup-20(29)-en-28-oic acid 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Synthesis and cytotoxic evaluation of novel ester-triazole-linked triterpenoid–AZT conjugates

  摘要：

  Betulinic acid and analogous naturally occurring triterpenoid acids were transformed into the corresponding propargyl esters and subsequently deployed as substrates for a click chemistry-mediated coupling with azidothymidine (AZT) en route to novel 1,2,3-triazole-tethered triterpenoid-AZT conjugates. Twelve new hybrids were thus prepared and assessed in terms of their cytotoxic activity, revealing an interesting anticancer activity of five triterpenoid-AZT hybrids on KB and Hep-G2 tumor cell lines. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.079
• 作为产物：
  描述：

  3α-hydroxylup-20(29)-en-23,28-dioic acid 在 potassium dichromate 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以76%的产率得到3-oxo-23-nor-lup-20(29)-en-28-oic acid
  参考文献：
  名称：

  Van Loc, Tran; Van Sung, Tran; Kamperdick, Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 1, p. 63 - 71

  摘要：

  DOI：

文献信息

• Synthesis and cytotoxic evaluation of novel amide–triazole-linked triterpenoid–AZT conjugates
  作者：Tuyet Anh Dang Thi、Nguyen Thi Kim Tuyet、Chinh Pham The、Ha Thanh Nguyen、Cham Ba Thi、Hoang Thi Phuong、Luu Van Boi、Tuyen Van Nguyen、Matthias D’hooghe

  DOI：10.1016/j.tetlet.2014.11.069

  日期：2015.1

  A variety of triterpenoid propargyl amides, prepared from the corresponding acids, was used as substrates for the construction of novel triazole-tethered triterpenoid-AZT conjugates via a click chemistry-mediated coupling with azidothymidine (AZT). Thus, nineteen new hybrids were successfully prepared and evaluated as cytotoxic agents, revealing an interesting anticancer activity of four triterpenoid AZT hybrids on KB and Hep-G2 tumor cell lines. (C) 2014 Elsevier Ltd. All rights reserved.
• Van Loc, Tran; Van Sung, Tran; Kamperdick, Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 1, p. 63 - 71
  作者：Van Loc, Tran、Van Sung, Tran、Kamperdick、Adam

  DOI：——

  日期：——
• Synthesis and cytotoxic evaluation of novel ester-triazole-linked triterpenoid–AZT conjugates
  作者：Tuyet Anh Dang Thi、Nguyen Thi Kim Tuyet、Chinh Pham The、Ha Thanh Nguyen、Cham Ba Thi、Tien Doan Duy、Matthias D’hooghe、Tuyen Van Nguyen

  DOI：10.1016/j.bmcl.2014.09.079

  日期：2014.11

  Betulinic acid and analogous naturally occurring triterpenoid acids were transformed into the corresponding propargyl esters and subsequently deployed as substrates for a click chemistry-mediated coupling with azidothymidine (AZT) en route to novel 1,2,3-triazole-tethered triterpenoid-AZT conjugates. Twelve new hybrids were thus prepared and assessed in terms of their cytotoxic activity, revealing an interesting anticancer activity of five triterpenoid-AZT hybrids on KB and Hep-G2 tumor cell lines. (C) 2014 Elsevier Ltd. All rights reserved.