(R)-(6,6-diphenyl-1,4-dioxan-2-yl)methanol | 1357157-79-9

• 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: (R)-(6,6-diphenyl-1,4-dioxan-2-yl)methanol
• 英文别名: [(2R)-6,6-diphenyl-1,4-dioxan-2-yl]methanol
• CAS: 1357157-79-9
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: BYJIFKDOSSFUIF-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(6,6-diphenyl-1,4-dioxan-2-yl)methanol 在 吡啶 、 三乙胺 作用下， 以 乙二醇乙醚 、 氯仿 为溶剂， 反应 6.0h， 生成 2-(2,6-dimethoxyphenoxy)-N-[[(2R)-6,6-diphenyl-1,4-dioxan-2-yl]methyl]ethanamine
  参考文献：
  名称：

  Structure–Activity Relationships in 1,4-Benzodioxan-Related Compounds. 11. Reversed Enantioselectivity of 1,4-Dioxane Derivatives in α₁-Adrenergic and 5-HT_1A Receptor Binding Sites Recognition

  摘要：

  5-HT1A receptor and alpha(1)-adrenoreceptor (alpha(1)-AR) binding sites recognized by the 1,4-dioxanes 2-4 display reversed stereochemical requirements. (S)-2 proved to be a potent 5-HT1A receptor agonist highly selective over alpha(1)-AR subtypes. Chirality influenced the anticancer activity of 3 and 4 in human prostate cancer cells (PC-3): (R)-4, eutomer at the alpha(1d)-AR subtype, was the most potent. The decreased effect of 4 and (R)-4 in alpha(1d)-AR silenced PC-3 cells confirmed that their anticancer activity was alpha(1d)-AR-dependent.

  DOI：

  10.1021/jm301525w
• 作为产物：
  描述：

  6,6-diphenyl-1,4-dioxane-2-carboxylic acid 在 锂硼氢 、 正丁基锂 、 草酰氯 、 水 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.75h， 生成 (R)-(6,6-diphenyl-1,4-dioxan-2-yl)methanol
  参考文献：
  名称：

  1,4-Dioxane, a Suitable Scaffold for the Development of Novel M₃ Muscarinic Receptor Antagonists

  摘要：

  In this study the modulation of the pharmacological profile from agonist to antagonist was successfully obtained by replacing the methyl group in position 6 of the 1,4-dioxane scaffold of the potent M-2/M-3 muscarinic agonist 1 with bulkier groups. In particular, the 6,6-diphenyl substitution provided the potent M-3 preferring antagonist (+/-)-17, which in in vivo study proved to be effective in reducing the volume-induced contractions of rat urinary bladder and was devoid of cardiovascular effects.

  DOI：

  10.1021/jm2013216

文献信息

• Structure–Activity Relationships in 1,4-Benzodioxan-Related Compounds. 11. Reversed Enantioselectivity of 1,4-Dioxane Derivatives in α₁-Adrenergic and 5-HT_1A Receptor Binding Sites Recognition
  作者：Alessandro Bonifazi、Alessandro Piergentili、Fabio Del Bello、Yogita Farande、Mario Giannella、Maria Pigini、Consuelo Amantini、Massimo Nabissi、Valerio Farfariello、Giorgio Santoni、Elena Poggesi、Amedeo Leonardi、Sergio Menegon、Wilma Quaglia

  DOI：10.1021/jm301525w

  日期：2013.1.24

  5-HT1A receptor and alpha(1)-adrenoreceptor (alpha(1)-AR) binding sites recognized by the 1,4-dioxanes 2-4 display reversed stereochemical requirements. (S)-2 proved to be a potent 5-HT1A receptor agonist highly selective over alpha(1)-AR subtypes. Chirality influenced the anticancer activity of 3 and 4 in human prostate cancer cells (PC-3): (R)-4, eutomer at the alpha(1d)-AR subtype, was the most potent. The decreased effect of 4 and (R)-4 in alpha(1d)-AR silenced PC-3 cells confirmed that their anticancer activity was alpha(1d)-AR-dependent.
• 1,4-Dioxane, a Suitable Scaffold for the Development of Novel M₃ Muscarinic Receptor Antagonists
  作者：Fabio Del Bello、Elisabetta Barocelli、Simona Bertoni、Alessandro Bonifazi、Mercedes Camalli、Gaetano Campi、Mario Giannella、Rosanna Matucci、Marta Nesi、Maria Pigini、Wilma Quaglia、Alessandro Piergentili

  DOI：10.1021/jm2013216

  日期：2012.2.23

  In this study the modulation of the pharmacological profile from agonist to antagonist was successfully obtained by replacing the methyl group in position 6 of the 1,4-dioxane scaffold of the potent M-2/M-3 muscarinic agonist 1 with bulkier groups. In particular, the 6,6-diphenyl substitution provided the potent M-3 preferring antagonist (+/-)-17, which in in vivo study proved to be effective in reducing the volume-induced contractions of rat urinary bladder and was devoid of cardiovascular effects.