methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-oleana-2,12-dien-28-oate | 1442016-29-6

• 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: methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-oleana-2,12-dien-28-oate
• 英文别名: methyl (4aS,6aR,6aS,6bR,8aR,12aS,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,4,5,6,6a,7,8,8a,12,13,14b-dodecahydropicene-4a-carboxylate
• CAS: 1442016-29-6
• 化学式: C₃₇H₅₉BO₄
• 分子量: 578.684
• InChiKey: HRPUAXMEELHZQH-HYSNQHMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.13
• 重原子数：
  42
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-oleana-2,12-dien-28-oate 在 草酰氯 、 氨 、 lithium iodide 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 55.5h， 生成 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-oleana-2,12-dien-28-amide
  参考文献：
  名称：

  Novel oleanolic vinyl boronates: Synthesis and antitumor activity

  摘要：

  A series of novel oleanane-type pentacyclic triterpenoids bearing a boronate ester moiety at C3 have been synthesized by palladium-catalyzed cross-coupling of bis(pinacolato)diboron with vinyl triflates, in the presence of base, and these compounds were fully characterized by 1D and 2D NMR techniques. Evaluation of their antiproliferative effects on a panel of hematological-based and solid tumor cell lines identified three active oleanolic vinyl boronates that inhibited the growth of leukemia (Jurkat, K562), Burkitt's lymphoma (Jijoye), cervix (Hela), colon (SW480), and ovary (SKOV-3) cancer cells without concomitant inhibition of non-tumoral human fibroblasts. Their mechanisms of action were investigated on the leukemia Jurkat cell line. The results show that the incorporation of boron in the oleanolic acid core combined with the presence of amide bonds afforded compounds with desirable biological effects such as apoptosis induction and inhibition of proteasomal activity on tumor cells, which makes them potential templates for further development in the anticancer drug setting. (c) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.040
• 作为产物：
  描述：

  3-KETO-齐墩果酸-28-甲酯 在 2,6-二叔丁基-4-甲基吡啶 、 trans-bis(triphenylphosphine)palladium dichloride 、 sodium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-oleana-2,12-dien-28-oate
  参考文献：
  名称：

  Novel oleanolic vinyl boronates: Synthesis and antitumor activity

  摘要：

  A series of novel oleanane-type pentacyclic triterpenoids bearing a boronate ester moiety at C3 have been synthesized by palladium-catalyzed cross-coupling of bis(pinacolato)diboron with vinyl triflates, in the presence of base, and these compounds were fully characterized by 1D and 2D NMR techniques. Evaluation of their antiproliferative effects on a panel of hematological-based and solid tumor cell lines identified three active oleanolic vinyl boronates that inhibited the growth of leukemia (Jurkat, K562), Burkitt's lymphoma (Jijoye), cervix (Hela), colon (SW480), and ovary (SKOV-3) cancer cells without concomitant inhibition of non-tumoral human fibroblasts. Their mechanisms of action were investigated on the leukemia Jurkat cell line. The results show that the incorporation of boron in the oleanolic acid core combined with the presence of amide bonds afforded compounds with desirable biological effects such as apoptosis induction and inhibition of proteasomal activity on tumor cells, which makes them potential templates for further development in the anticancer drug setting. (c) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.040

文献信息

• Novel oleanolic vinyl boronates: Synthesis and antitumor activity
  作者：Vânia M. Moreira、Jorge A.R. Salvador、Sérgio Simões、Federica Destro、Riccardo Gavioli

  DOI：10.1016/j.ejmech.2013.01.040

  日期：2013.5

  A series of novel oleanane-type pentacyclic triterpenoids bearing a boronate ester moiety at C3 have been synthesized by palladium-catalyzed cross-coupling of bis(pinacolato)diboron with vinyl triflates, in the presence of base, and these compounds were fully characterized by 1D and 2D NMR techniques. Evaluation of their antiproliferative effects on a panel of hematological-based and solid tumor cell lines identified three active oleanolic vinyl boronates that inhibited the growth of leukemia (Jurkat, K562), Burkitt's lymphoma (Jijoye), cervix (Hela), colon (SW480), and ovary (SKOV-3) cancer cells without concomitant inhibition of non-tumoral human fibroblasts. Their mechanisms of action were investigated on the leukemia Jurkat cell line. The results show that the incorporation of boron in the oleanolic acid core combined with the presence of amide bonds afforded compounds with desirable biological effects such as apoptosis induction and inhibition of proteasomal activity on tumor cells, which makes them potential templates for further development in the anticancer drug setting. (c) 2013 Elsevier Masson SAS. All rights reserved.