12-(2-oxiranylmethoxy)abieta-8,11,13-trien-7-one | 917953-57-2

• 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: 12-(2-oxiranylmethoxy)abieta-8,11,13-trien-7-one
• 英文别名: (4aS,10aS)-1,1,4a-trimethyl-6-(oxiran-2-ylmethoxy)-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one
• CAS: 917953-57-2
• 化学式: C₂₃H₃₂O₃
• 分子量: 356.505
• InChiKey: PYNHDTKVKKWLAJ-LBRSZHJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  12-(2-oxiranylmethoxy)abieta-8,11,13-trien-7-one 、 2-氨基-2-甲基-1,3-丙二醇 以 甲醇 为溶剂， 反应 15.0h， 以86%的产率得到12-(2-hydroxy-3-{[2-hydroxy-1-(hydroxymethyl)-1-methylethyl]amino}propoxy)abieta-8,11,13-trien-7-one
  参考文献：
  名称：

  Synthesis and antiproliferative activity of novel sugiol β-amino alcohol analogs

  摘要：

  A series of P-amino alcohol analogs of sugiol were synthesized in a straightforward manner. The in vitro antiproliferative activities were examined in the human solid tumor cell lines A2780, SW1573 and WiDr. The most potent analogs induced considerably growth inhibition in the range 1.5-6.7 mu M. The results showed that beta-amino alcohol analogs are more potent than the parent compound. In addition, the derivatives with secondary amine fiagments showed more active than those bearing tertiary amines. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.06.001
• 作为产物：
  描述：

  柳杉酚 、 环氧溴丙烷 在 sodium hydride 作用下， 反应 20.0h， 以93%的产率得到12-(2-oxiranylmethoxy)abieta-8,11,13-trien-7-one
  参考文献：
  名称：

  Synthesis and antiproliferative activity of novel sugiol β-amino alcohol analogs

  摘要：

  A series of P-amino alcohol analogs of sugiol were synthesized in a straightforward manner. The in vitro antiproliferative activities were examined in the human solid tumor cell lines A2780, SW1573 and WiDr. The most potent analogs induced considerably growth inhibition in the range 1.5-6.7 mu M. The results showed that beta-amino alcohol analogs are more potent than the parent compound. In addition, the derivatives with secondary amine fiagments showed more active than those bearing tertiary amines. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.06.001