methyl 2,3-(2-amino,4-phenyl)-pyrimidinyl-olean-12-en-28-oate | 1579240-71-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: methyl 2,3-(2-amino,4-phenyl)-pyrimidinyl-olean-12-en-28-oate
• 英文别名: methyl (1R,2R,11R,14R,15S,18S,23S)-7-amino-2,10,10,14,15,21,21-heptamethyl-5-phenyl-6,8-diazahexacyclo[12.12.0.02,11.04,9.015,24.018,23]hexacosa-4,6,8,24-tetraene-18-carboxylate
• CAS: 1579240-71-3
• 化学式: C₃₉H₅₃N₃O₂
• 分子量: 595.869
• InChiKey: PJZKEACMAYLMRU-PKGZJSIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  44
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  78.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  齐墩果酸甲酯 在 pyridinium chlorochromate 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 methyl 2,3-(2-amino,4-phenyl)-pyrimidinyl-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

• Synthesis of novel ring-A fused hybrids of oleanolic acid with capabilities to arrest cell cycle and induce apoptosis in breast cancer cells
  作者：Uppuluri Venkata Mallavadhani、Nagi Reddy Vanga、Manish Kumar Jeengar、V.G.M. Naidu

  DOI：10.1016/j.ejmech.2013.12.040

  日期：2014.3

  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.