(2R,3R,4S,4aS,5R,8aS)-5-bromo-3,4-dihydroxy-8a-methyl-1,3,4,5,6,8a-hexahydro-2H-2,4a-epoxynaphthalen-8-yl trifluoromethanesulfonate | 1203511-31-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (2R,3R,4S,4aS,5R,8aS)-5-bromo-3,4-dihydroxy-8a-methyl-1,3,4,5,6,8a-hexahydro-2H-2,4a-epoxynaphthalen-8-yl trifluoromethanesulfonate
• CAS: 1203511-31-2
• 化学式: C₁₂H₁₄BrF₃O₆S
• 分子量: 423.205
• InChiKey: AZRUTZFQCLRNAH-SJCQGDPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,4aS,5R,8aS)-5-bromo-3,4-dihydroxy-8a-methyl-1,3,4,5,6,8a-hexahydro-2H-2,4a-epoxynaphthalen-8-yl trifluoromethanesulfonate 、 三乙基硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以0.053 g的产率得到[(1S,2R,6S,8R,9R,10S)-2-bromo-10-hydroxy-6-methyl-9-triethylsilyloxy-11-oxatricyclo[6.2.1.01,6]undec-4-en-5-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  Chemical and Biological Studies of Nakiterpiosin and Nakiterpiosinone

  摘要：

  Nakiterpiosin and nakiterpiosinone are two related C-nor-D-homosteroids isolated from the sponge Terpios hoshinota that show promise as anticancer agents. We have previously described the asymmetric synthesis and revision of the relative configuration of nakiterpiosin. We now provide detailed information on the stereochemical analysis that supports our structure revision and the synthesis of the originally proposed and revised nakiterpiosin. In addition, we herein describe a refined approach for the synthesis of nakiterpiosin, the first synthesis of nakiterpiosinone, and preliminary mechanistic studies of nakiterpiosin's action in mammalian cells. Cells treated with nakiterpiosin exhibit compromised formation of the primary cilium, an organelle that functions as an assembly point for components of the Hedgehog signal transduction pathway. We provide evidence that the biological effects exhibited by nakiterpiosin are mechanistically distinct from those of well-established antimitotic agents such as taxol. Nakiterpiosin may be useful as an anticancer agent in those tumors resistant to existing antimitotic agents and those dependent on Hedgehog pathway responses for growth.

  DOI：

  10.1021/ja908626k
• 作为产物：
  描述：

  [(1S,2R,6S,8R,10R)-2-bromo-10-hydroxy-6-methyl-9-oxo-11-oxatricyclo[6.2.1.01,6]undec-4-en-5-yl] trifluoromethanesulfonate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.25h， 生成 (2R,3R,4S,4aS,5R,8aS)-5-bromo-3,4-dihydroxy-8a-methyl-1,3,4,5,6,8a-hexahydro-2H-2,4a-epoxynaphthalen-8-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Chemical and Biological Studies of Nakiterpiosin and Nakiterpiosinone

  摘要：

  Nakiterpiosin and nakiterpiosinone are two related C-nor-D-homosteroids isolated from the sponge Terpios hoshinota that show promise as anticancer agents. We have previously described the asymmetric synthesis and revision of the relative configuration of nakiterpiosin. We now provide detailed information on the stereochemical analysis that supports our structure revision and the synthesis of the originally proposed and revised nakiterpiosin. In addition, we herein describe a refined approach for the synthesis of nakiterpiosin, the first synthesis of nakiterpiosinone, and preliminary mechanistic studies of nakiterpiosin's action in mammalian cells. Cells treated with nakiterpiosin exhibit compromised formation of the primary cilium, an organelle that functions as an assembly point for components of the Hedgehog signal transduction pathway. We provide evidence that the biological effects exhibited by nakiterpiosin are mechanistically distinct from those of well-established antimitotic agents such as taxol. Nakiterpiosin may be useful as an anticancer agent in those tumors resistant to existing antimitotic agents and those dependent on Hedgehog pathway responses for growth.

  DOI：

  10.1021/ja908626k