(4R,4aR,5R,11bS)-methyl 1,2,3,4,4a,5,6,11b-octahydro-5-hydroxy-4,11b-dimethylphenanthro[3,2-b]furan-4-carboxylate | 1612793-62-0

• 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: (4R,4aR,5R,11bS)-methyl 1,2,3,4,4a,5,6,11b-octahydro-5-hydroxy-4,11b-dimethylphenanthro[3,2-b]furan-4-carboxylate
• 英文别名: methyl (4R,4aR,5R,11bS)-5-hydroxy-4,11b-dimethyl-1,2,3,4a,5,6-hexahydronaphtho[2,1-f][1]benzofuran-4-carboxylate
• CAS: 1612793-62-0
• 化学式: C₂₀H₂₄O₄
• 分子量: 328.408
• InChiKey: DBLRELQFSMTLPI-RARDXLECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,4aR,5R,11bS)-methyl 1,2,3,4,4a,5,6,11b-octahydro-5-hydroxy-4,11b-dimethylphenanthro[3,2-b]furan-4-carboxylate 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以82%的产率得到(4R,4aR,5R,11bS)-1,2,3,4,4a,5,6,11b-octahydro-5-hydroxy-4,11b-dimethylphenanthro[3,2-b]furan-4-carboxylic acid
  参考文献：
  名称：

  Identification of Gli-mediated transcription inhibitors through synthesis and evaluation of taepeenin D analogues

  摘要：

  与Taepeenin D相关的松香酸衍生物被鉴定为新的Hh通路抑制剂，其作用于Smo下游。

  DOI：

  10.1039/c6md00354k
• 作为产物：
  描述：

  methyl (4R,4aR,11bS)-6,8-dihydroxy-4,11b-dimethyl-1,2,3,4,4a,5,6,8,9,11b-decahydrophenanthro[3,2-b]furan-4-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 三乙醇胺 、 5% palladium on barium sulphate 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 水 、 苯 为溶剂， 反应 101.5h， 生成 (4R,4aR,5R,11bS)-methyl 1,2,3,4,4a,5,6,11b-octahydro-5-hydroxy-4,11b-dimethylphenanthro[3,2-b]furan-4-carboxylate
  参考文献：
  名称：

  A Fast Entry to Furanoditerpenoid-Based Hedgehog Signaling Inhibitors: Identifying Essential Structural Features

  摘要：

  New, small molecule Hedgehog (Hh) pathway inhibitors, such as the furanoditerpenoid taepeenin D, are of high medicinal importance. To establish key structure-activity relationships (SARs) for this lead, a synthetic sequence has been developed for the expedient preparation of several derivatives and their evaluation as Hh inhibitors exploiting its structural similarity to abietic acid. While C(14) substitution is not essential for biological activity, the presence of a hydrogen bond acceptor at C(6) and an intact benzofuran moiety are.

  DOI：

  10.1021/ol501370j

文献信息

• Identification of Gli-mediated transcription inhibitors through synthesis and evaluation of taepeenin D analogues
  作者：A. Antoniou、M. Chatzopoulou、M. Bantzi、C. M. Athanassopoulos、A. Giannis、E. N. Pitsinos

  DOI：10.1039/c6md00354k

  日期：——

  Abietic acid derivatives related to taepeenin D were identified as new Hh pathway inhibitors that operate downstream of Smo.

  与Taepeenin D相关的松香酸衍生物被鉴定为新的Hh通路抑制剂，其作用于Smo下游。
• A Fast Entry to Furanoditerpenoid-Based Hedgehog Signaling Inhibitors: Identifying Essential Structural Features
  作者：Maria Chatzopoulou、Antonia Antoniou、Emmanuel N. Pitsinos、Marina Bantzi、Sofia D. Koulocheri、Serkos A. Haroutounian、Athanassios Giannis

  DOI：10.1021/ol501370j

  日期：2014.6.20

  New, small molecule Hedgehog (Hh) pathway inhibitors, such as the furanoditerpenoid taepeenin D, are of high medicinal importance. To establish key structure-activity relationships (SARs) for this lead, a synthetic sequence has been developed for the expedient preparation of several derivatives and their evaluation as Hh inhibitors exploiting its structural similarity to abietic acid. While C(14) substitution is not essential for biological activity, the presence of a hydrogen bond acceptor at C(6) and an intact benzofuran moiety are.