3α,11α-dihydroxy-lup-20(29)-ene-23,28-dioic acid | 94662-82-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3α,11α-dihydroxy-lup-20(29)-ene-23,28-dioic acid
• 英文别名: 3α,11α-dihydroxy-lup-20(29)-en-23,28-dioic acid；(1R,3aS,5aR,5bR,7aR,8S,9R,11aS,11bR,12R,13aR,13bR)-9,12-dihydroxy-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a,8-dicarboxylic acid
• CAS: 94662-82-5
• 化学式: C₃₀H₄₆O₆
• 分子量: 502.692
• InChiKey: VZYJGZZXVOHUMY-DPPLFAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3α,11α-dihydroxy-lup-20(29)-ene-23,28-dioic acid 在 chromium(VI) oxide 、 copper(l) iodide 、 硫酸 、 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 12.0h， 生成 [1-[(2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]triazol-4-yl]methyl (1R,3aS,5aR,5bR,7aS,8R,11aS,11bR,13aR,13bR)-5a,5b,8,11a-tetramethyl-9,12-dioxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,8,10,11,11b,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate
  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,11α-dihydroxylup-20(29)-ene-23,28-dioic acid 28-O-<α-L-rhamnopyranosyl(1->4)-O-β-D-glucopyranosyl(1->6)>-β-D-glucopyranoside 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以28 mg的产率得到3α,11α-dihydroxy-lup-20(29)-ene-23,28-dioic acid
  参考文献：
  名称：

  来自鹅掌楸的三萜糖苷

  摘要：

  除了 3-epi-桦木酸外，还从鹅掌楸叶中分离出三种三萜糖苷。已确定糖苷的结构为 28-O-[α-L-吡喃鼠李糖基(1----4)-O-β-D-吡喃葡萄糖基(1----6)-be ta-D-吡喃葡萄糖苷3 alpha-hydroxy-lup-20(29)-ene-23,28-dioic acid, 3 alpha,11 alpha-dihydroxy-lup20(29)-ene-23,28-dioic acid and 3-epi-betulinic acid通过光谱数据和化学转化。最后两种化合物首次在植物界被发现。

  DOI：

  10.1016/0031-9422(91)83647-4

文献信息

• 3α,11α-Dihydroxylup-20(29)-ene-23,28-dioic acid from Schefflera octophylla
  作者：M. Lischewski、Ph.D. Ty、J. Schmidt、A. Preiss、H.V. Phiet、G. Adam

  DOI：10.1016/s0031-9422(00)83471-8

  日期：1984.1

  Abstract The main triterpene from leaves of Schefflera octophylla was isolated in a high yield (7%) and its structure determined as 3α-hydroxy-lup-20(29)-

  摘要 以高产率（7%）分离出鹅掌楸叶中的主要三萜，其结构确定为3α-羟基-lup-20(29)-
• SUNG, T. V.;STEGLICH, W.;ADAM, G., PHYTOCHEMISTRY, 30,(1991) N, C. 2349-2356
  作者：SUNG, T. V.、STEGLICH, W.、ADAM, G.

  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.
• Triterpene glycosides from Schefflera octophylla
  作者：T.V. Sung、W. Steglich、G. Adam

  DOI：10.1016/0031-9422(91)83647-4

  日期：1991.1

  3-epi-betulinic acid, three triterpene glycosides were isolated from leaves of Schefflera octophylla. The structures of the glycosides have been determined as 28-O-[alpha-L-rhamnopyranosyl(1----4)-O-beta-D-glucopyranosyl(1----6)-be ta-D- glucopyranosides of 3 alpha-hydroxy-lup-20(29)-ene-23,28-dioic acid, 3 alpha,11 alpha- dihydroxy-lup20(29)-ene-23,28-dioic acid and 3-epi-betulinic acid by spectroscopic

  除了 3-epi-桦木酸外，还从鹅掌楸叶中分离出三种三萜糖苷。已确定糖苷的结构为 28-O-[α-L-吡喃鼠李糖基(1----4)-O-β-D-吡喃葡萄糖基(1----6)-be ta-D-吡喃葡萄糖苷3 alpha-hydroxy-lup-20(29)-ene-23,28-dioic acid, 3 alpha,11 alpha-dihydroxy-lup20(29)-ene-23,28-dioic acid and 3-epi-betulinic acid通过光谱数据和化学转化。最后两种化合物首次在植物界被发现。