methyl 3-oxo-2-benzylidene-olean-12-en-28-oate | 170240-93-4

• 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-oxo-2-benzylidene-olean-12-en-28-oate
• 英文别名: methyl-3-oxo-2-phenylmethylene-olean-12-ene-28-methyl ester；methyl 2-benzylidene-3-oxooleanate
• CAS: 170240-93-4
• 化学式: C₃₈H₅₂O₃
• 分子量: 556.829
• InChiKey: VJWPNVXLBYCYHC-RXLVGJJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.22
• 重原子数：
  41.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 3-oxo-2-benzylidene-olean-12-en-28-oate 在 一水合肼 作用下， 以 乙醇 为溶剂， 以72%的产率得到methyl 2,3-(5-phenyl)-4,5-dihydro-1H-pyrazolo-olean-12-en-28-oate
  参考文献：
  名称：

  Synthesis of novel ring-A fused hybrids of oleanolic acid with capabilities to arrest cell cycle and induce apoptosis in breast cancer cells

  摘要：

  Six novel oleanolic acid ring-A fused hybrids (5-10) have been synthesized by employing a four step protocol with the introduction of benzylidene functionality at C-2 as the key step. Their structures were established by high resolution NMR and Mass spectral data. The synthesized compounds have been screened against seven human cancer cell lines including ME-180 & HeLa (cervix), MCF-7, MDA-MB-453 & MDA-MB-231 (breast), PC-3 (prostate) and HT-29 (colon) using MIT assay. Most significantly, compound 10 showed potent activity against the three breast cancer cell lines. The IC50 value (10.60 mu M) of compound 10 against MCF-7 found to be much lower than that of the standards and parent compound. Flow cytometric analysis reveals that compound 10 arrests cell cycle in S phase and induces apoptosis in MCF cells. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.040
• 作为产物：
  描述：

  齐墩果酸 在 potassium carbonate 、 pyridinium chlorochromate 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 16.0h， 生成 methyl 3-oxo-2-benzylidene-olean-12-en-28-oate
  参考文献：
  名称：

  Synthesis of novel ring-A fused hybrids of oleanolic acid with capabilities to arrest cell cycle and induce apoptosis in breast cancer cells

  摘要：

  Six novel oleanolic acid ring-A fused hybrids (5-10) have been synthesized by employing a four step protocol with the introduction of benzylidene functionality at C-2 as the key step. Their structures were established by high resolution NMR and Mass spectral data. The synthesized compounds have been screened against seven human cancer cell lines including ME-180 & HeLa (cervix), MCF-7, MDA-MB-453 & MDA-MB-231 (breast), PC-3 (prostate) and HT-29 (colon) using MIT assay. Most significantly, compound 10 showed potent activity against the three breast cancer cell lines. The IC50 value (10.60 mu M) of compound 10 against MCF-7 found to be much lower than that of the standards and parent compound. Flow cytometric analysis reveals that compound 10 arrests cell cycle in S phase and induces apoptosis in MCF cells. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.040

文献信息

• Zaprutko, L., Polish Journal of Chemistry, 1995, vol. 69, # 7, p. 1003 - 1012
  作者：Zaprutko, L.

  DOI：——

  日期：——