toluene-4-sulfonic acid 6-Allyl-3-hydroxy-3,6-dihydro-2H-pyran-2-ylmethyl ester | 101208-79-1

• 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: toluene-4-sulfonic acid 6-Allyl-3-hydroxy-3,6-dihydro-2H-pyran-2-ylmethyl ester
• 英文别名: [(2R,3S,6R)-3-hydroxy-6-prop-2-enyl-3,6-dihydro-2H-pyran-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 101208-79-1
• 化学式: C₁₆H₂₀O₅S
• 分子量: 324.398
• InChiKey: CFGTVSJEMYJLCZ-VNQPRFMTSA-N

物化性质

• 沸点：
  491.6±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  toluene-4-sulfonic acid 6-Allyl-3-hydroxy-3,6-dihydro-2H-pyran-2-ylmethyl ester 在 草酰氯 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 甲苯 、 苯 为溶剂， 生成
  参考文献：
  名称：

  在5- exo环氧开口上激活6- endo。四氢吡喃系统的环选择性形成和短毒素B的ABC环骨架的立体控制合成

  摘要：

  对于涉及6-四氢吡喃系统的区域选择性和立体特异性合成的新的合成策略内的环氧化物的开口和它的应用程序了到建设ABC短裸B的环体系中有描述。

  DOI：

  10.1039/c39850001359
• 作为产物：
  描述：

  (2R,3S,6R)-6-allyl-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol 在 吡啶 、 对甲苯磺酰氯 作用下， 反应 8.0h， 以65%的产率得到toluene-4-sulfonic acid 6-Allyl-3-hydroxy-3,6-dihydro-2H-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Medicinal Chemistry of Dihydropyran-Based Medium Ring Macrolides Related to Aspergillides: Selective Inhibition of PI3Kα

  摘要：

  A set of nine trans-disubstituted dihydropyran-based medium ring macrolides has been synthesized using D-glucal as chiral pool and evaluated against a panel of three human cancer cell lines and a normal cell line. The synthetic route to the targeted molecule is simple, concise, and high yielding compared to other reported methods. Bioevaluation studies have resulted in the identification of a potent cytotoxic molecule (10) exhibiting dose-dependent growth inhibition against HL-60 cell line with an IC50 value of 1.10 +/- 0.075 mu M, which is lower than that of naturally occurring molecules of this class and of comparable activity to the synthetic drug fludarubin. Compound 10 inhibits the PI3K/AKT signaling pathway by selectively targeting the p110 alpha subunit of PI3K alpha. This leads to mitochondrial stress that causes translocation of cytochrome c from mitochondria to cytosol, which in turn activates caspase-mediated apoptotic cell death. Further in silico docking simulations of four macrolides with p110 alpha subunits have been carried out to visualize the orientation pattern.

  DOI：

  10.1021/jm400515c

文献信息

• Activation of 6-endo over 5-exo epoxide openings. Ring-selective formation of tetrahydropyran systems and stereocontrolled synthesis of the ABC ring framework of brevetoxin B
  作者：K. C. Nicolaou、M. E. Duggan、C-K. Hwang、P. K. Somers

  DOI：10.1039/c39850001359

  日期：——

  A new synthetic strategy for the regio- and stereo-specific synthesis of tetrahydropyran systems involving 6-endo epoxide openings and its applicaiton to the construction of the ABC ring system of brevetoxin B are described.

  对于涉及6-四氢吡喃系统的区域选择性和立体特异性合成的新的合成策略内的环氧化物的开口和它的应用程序了到建设ABC短裸B的环体系中有描述。
• Medicinal Chemistry of Dihydropyran-Based Medium Ring Macrolides Related to Aspergillides: Selective Inhibition of PI3Kα
  作者：Mallikharjuna R. Lambu、Suresh Kumar、Syed K. Yousuf、Deepak K. Sharma、Altaf Hussain、Ajay Kumar、Fayaz Malik、Debaraj Mukherjee

  DOI：10.1021/jm400515c

  日期：2013.8.8

  A set of nine trans-disubstituted dihydropyran-based medium ring macrolides has been synthesized using D-glucal as chiral pool and evaluated against a panel of three human cancer cell lines and a normal cell line. The synthetic route to the targeted molecule is simple, concise, and high yielding compared to other reported methods. Bioevaluation studies have resulted in the identification of a potent cytotoxic molecule (10) exhibiting dose-dependent growth inhibition against HL-60 cell line with an IC50 value of 1.10 +/- 0.075 mu M, which is lower than that of naturally occurring molecules of this class and of comparable activity to the synthetic drug fludarubin. Compound 10 inhibits the PI3K/AKT signaling pathway by selectively targeting the p110 alpha subunit of PI3K alpha. This leads to mitochondrial stress that causes translocation of cytochrome c from mitochondria to cytosol, which in turn activates caspase-mediated apoptotic cell death. Further in silico docking simulations of four macrolides with p110 alpha subunits have been carried out to visualize the orientation pattern.