[(4R)-16-benzoyloxy-4-methyl-2-oxo-3-oxabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl] benzoate | 1276020-13-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: [(4R)-16-benzoyloxy-4-methyl-2-oxo-3-oxabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl] benzoate
• CAS: 1276020-13-3
• 化学式: C₃₀H₃₀O₆
• 分子量: 486.565
• InChiKey: PGPVMDBUSYDCKD-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (4R)-14,16-dimethoxy-4-methyl-3-oxabicyclo[10.4.0]hexadeca-1(12),8,13,15-tetraen-2-one 在 palladium 10% on activated carbon 、 氢气 、 三溴化硼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 0.33h， 生成 [(4R)-16-benzoyloxy-4-methyl-2-oxo-3-oxabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl] benzoate
  参考文献：
  名称：

  Synthesis, modification, and evaluation of (R)-de-O-methyllasiodiplodin and analogs as nonsteroidal antagonists of mineralocorticoid receptor

  摘要：

  Macrolide (R)-de-O-methyllasiodiplodin (1), discovered to be a potent nonsteroidal antagonist of the mineralocorticoid receptor (MR), was synthesized via an efficient method and evaluated for MR antagonistic activity together with its analogs. Among all the tested compounds, compounds 18a, 18b and 18c, exhibited more potent antagonistic activity against MR with IC50 values ranging from 0.58 to 1.11 mu M. Generally, it was obviously demonstrated that acetylation at phenolic hydroxyl groups and the ring size in analogs of 1 were very important for MR antagonist activity. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.101

文献信息

• Synthesis, modification, and evaluation of (R)-de-O-methyllasiodiplodin and analogs as nonsteroidal antagonists of mineralocorticoid receptor
  作者：Cheng-Shi Jiang、Rong Zhou、Jing-Xu Gong、Li-Li Chen、Tibor Kurtán、Xu Shen、Yue-Wei Guo

  DOI：10.1016/j.bmcl.2010.12.101

  日期：2011.2

  Macrolide (R)-de-O-methyllasiodiplodin (1), discovered to be a potent nonsteroidal antagonist of the mineralocorticoid receptor (MR), was synthesized via an efficient method and evaluated for MR antagonistic activity together with its analogs. Among all the tested compounds, compounds 18a, 18b and 18c, exhibited more potent antagonistic activity against MR with IC50 values ranging from 0.58 to 1.11 mu M. Generally, it was obviously demonstrated that acetylation at phenolic hydroxyl groups and the ring size in analogs of 1 were very important for MR antagonist activity. (c) 2010 Elsevier Ltd. All rights reserved.