(4R,6R,8R,11E,13R)-16-chloro-13,19-dihydroxy-17-methoxy-4-methyl-3,7-dioxatricyclo[13.4.0.06,8]nonadeca-1(15),11,16,18-tetraen-2-one | 1178898-24-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (4R,6R,8R,11E,13R)-16-chloro-13,19-dihydroxy-17-methoxy-4-methyl-3,7-dioxatricyclo[13.4.0.06,8]nonadeca-1(15),11,16,18-tetraen-2-one
• CAS: 1178898-24-2
• 化学式: C₁₉H₂₃ClO₆
• 分子量: 382.841
• InChiKey: YXIXMWJMLDYKJG-OWLNNGPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  88.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (4R,6R,8R,11E,13R)-16-chloro-13,17,19-trihydroxy-4-methyl-3,7-dioxatricyclo[13.4.0.06,8]nonadeca-1(15),11,16,18-tetraen-2-one 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以18.1%的产率得到(4R,6R,8R,11E,13R)-16-chloro-13,19-dihydroxy-17-methoxy-4-methyl-3,7-dioxatricyclo[13.4.0.06,8]nonadeca-1(15),11,16,18-tetraen-2-one
  参考文献：
  名称：

  Synthesis and structure–activity relationships of radicicol derivatives and WNT-5A expression inhibitory activity

  摘要：

  WNT-5A, a secretory glycoprotein, is related to the proliferation of dermal papilla cells. To develop a hair-growth stimulant, we have been searching for inhibitors of WNT-5A expression. We identified radicicol (1) as an active compound, and synthesized several radicicol derivatives. Among them, 6,7-dihydro-10 alpha-hydroxy radicicol (31) was found to function as a new potent WNT-5A expression inhibitor with relatively low toxicity and excellent stability. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.060