3β,28-di-(2-cyanoethoxy)lup-20(29)-en | 1309960-47-1

• 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: 3β,28-di-(2-cyanoethoxy)lup-20(29)-en
• 英文别名: 3β,28-di(2-cyanoethoxy)lup-20(29)-ene；3-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-(2-cyanoethoxy)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-3a-yl]methoxy]propanenitrile
• CAS: 1309960-47-1
• 化学式: C₃₆H₅₆N₂O₂
• 分子量: 548.853
• InChiKey: CIAZRBCFHDTXAV-XEKQMHMZSA-N

物化性质

• 熔点：
  175-177 °C
• 沸点：
  644.6±30.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.87
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  66.04
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3β,28-di-(2-cyanoethoxy)lup-20(29)-en 在 氢气 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以82%的产率得到3β,28-di-O-[3-(aminopropoxy)]lup-20(29)-en
  参考文献：
  名称：

  桦木醇、高根二醇和紫杉醇的氨基丙氧基衍生物的合成和抗肿瘤活性

  摘要：

  桦木醇、高根二醇、紫杉醇和齐墩果三醇的氨基丙氧基衍生物已经通过三萜类化合物的羟基的氰乙基化以及随后的氰乙基片段的还原来合成。已发现 3β,28-di-O-[3-(aminopropoxy)]lupa-20(29)-ene 和 3β-O-hydroxy-28-O-[3-(aminopropoxy)]olean-12- ene对多种人类肿瘤细胞系具有高体外抗肿瘤活性。已经表明，氨基丙氧基片段是合成基于三萜类化合物的抗癌剂中的一种新的有前景的药效团。

  DOI：

  10.1134/s1068162011030101
• 作为产物：
  描述：

  28-acetoxybetulin 在 苄基三乙基氯化铵 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 48.0h， 生成 3-[3β-hydroxylup-20(29)-en-28-yloxy]propanenitrile 、 3β,28-di-(2-cyanoethoxy)lup-20(29)-en
  参考文献：
  名称：

  Synthetic transformations of higher terpenoids: XXIV. Synthesis of cyanoethyl derivatives of lupane triterpenoids and their transformation into 1,2,4-oxadiazoles

  摘要：

  Cyanoethylation of lupane triterpenoids was performed. Amide oximes of 3 beta-O-(2-cyanoethyl)-betulinic acid methyl ester and 3 beta-O-acetyl-28-O-(2-cyanoethyl)betulin and the corresponding O-[2-(1,2,4-oxadiazol-3-yl)ethyl] lupane derivatives were obtained.

  DOI：

  10.1134/s1070428011040208

文献信息

• Synthesis and anticancer activity of aminopropoxytriterpenoids
  作者：Gulnara V. Giniyatyllina、Irina E. Smirnova、Oxana B. Kazakova、Nadejda P. Yavorskaya、Irina S. Golubeva、Olga S. Zhukova、Rujena B. Pugacheva、Galina N. Apryshko、Vladimir V. Poroikov

  DOI：10.1007/s00044-015-1392-y

  日期：2015.9

  Triterpenoids with aminopropoxy groups in C-28 or C-3 and C-28 positions were synthesized from betulin, erythrodiol, uvaol, oleantriol and betulinic acid N-methylpiperazinylamide by cyanoethylation and the following catalytic hydrogenolysis. Computational estimating activity spectra of the designed compounds pointed out on their probable antineoplastic and proapoptotic activities. Their in vitro cytotoxic activity was evaluated at the National Cancer Institute, USA. Aminopropoxy derivatives of betulin, erythrodiol and oleantriol demonstrated the highest cytotoxic activity toward the most of 60 used tumor cell lines. Bisaminopropoxyerythrodiol revealed in vivo significant antineoplastic activity toward five mouse solid transplantable tumors. The results of in silico investigations and the efficacy of compounds in a broad panel of cell lines in vitro and the activity of bisaminopropoxyerythrodiol on the in vivo tumor models strongly suggest aminopropoxytriterpenoids as promising compounds for further investigation as anticancer agents.