((3-bromo-2-methylbenzyl)oxy)(tert-butyl)dimethylsilane | 1160872-79-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((3-bromo-2-methylbenzyl)oxy)(tert-butyl)dimethylsilane
• CAS: 1160872-79-6
• 化学式: C₁₄H₂₃BrOSi
• 分子量: 315.326
• InChiKey: LHZOIQBDVUGNKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (1-(tert-butoxycarbonyl)piperidin-4-yl)zinc iodide 、 ((3-bromo-2-methylbenzyl)oxy)(tert-butyl)dimethylsilane 在 copper(l) iodide 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以53%的产率得到
  参考文献：
  名称：

  Synthesis and SAR of tolylamine 5-HT6 antagonists

  摘要：

  The synthesis and SAR of tolylamines with 5-HT6 receptor antagonist activity is presented. The amine, core aromatic, peripheral aromatic, and ether linker moieties of HTS hit 1 were modulated and the effect on potency at 5-HT6 examined. Tolylpiperidine ether 9h was found to possess desirable pharmacokinetic (PK) properties, and was also shown to enhance cognition in the rat novel object recognition paradigm. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.077
• 作为产物：
  描述：

  3-溴-2-甲基苯甲醇 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以64%的产率得到((3-bromo-2-methylbenzyl)oxy)(tert-butyl)dimethylsilane
  参考文献：
  名称：

  Synthesis and SAR of tolylamine 5-HT6 antagonists

  摘要：

  The synthesis and SAR of tolylamines with 5-HT6 receptor antagonist activity is presented. The amine, core aromatic, peripheral aromatic, and ether linker moieties of HTS hit 1 were modulated and the effect on potency at 5-HT6 examined. Tolylpiperidine ether 9h was found to possess desirable pharmacokinetic (PK) properties, and was also shown to enhance cognition in the rat novel object recognition paradigm. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.077

文献信息

• Chemical and Biological Studies of Nakiterpiosin and Nakiterpiosinone
  作者：Shuanhu Gao、Qiaoling Wang、Lily Jun-Shen Huang、Lawrence Lum、Chuo Chen

  DOI：10.1021/ja908626k

  日期：2010.1.13

  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.