lasicicol | 1179820-08-6

• 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: lasicicol
• 英文别名: (3R)-nordinone；(-)-(R)-nordinone；nordinone；(4R)-16,18-dihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),15,17-triene-2,12-dione
• CAS: 1179820-08-6
• 化学式: C₁₈H₂₄O₅
• 分子量: 320.386
• InChiKey: JBVLZTRASUVBJM-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Monocillin II 在 5%-palladium/activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.5h， 以74.7%的产率得到lasicicol
  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

文献信息

• Synthesis and structure–activity relationships of radicicol derivatives and WNT-5A expression inhibitory activity
  作者：Hideki Shinonaga、Toshiya Noguchi、Akiko Ikeda、Mari Aoki、Natsuko Fujimoto、Akira Kawashima

  DOI：10.1016/j.bmc.2009.04.060

  日期：2009.7

  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.