(±)-1-(2-fluorophenyl)-2-methyl-2-(pyridin-3-yl)-1-propanol | 1423566-63-5

• 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: (±)-1-(2-fluorophenyl)-2-methyl-2-(pyridin-3-yl)-1-propanol
• CAS: 1423566-63-5
• 化学式: C₁₅H₁₆FNO
• 分子量: 245.297
• InChiKey: AWBPNTBJFXGRGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  33.12
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (±)-1-(2-fluorophenyl)-2-methyl-2-(pyridin-3-yl)-1-propanol 在 吡啶 、 (1S)-(+)-10-camphorsulfonic acid 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 22.25h， 生成
  参考文献：
  名称：

  [³H]Metyrapol and 4-[¹³¹I]Iodometomidate Label Overlapping, but Not Identical, Binding Sites on Rat Adrenal Membranes

  摘要：

  Metyrapone, metyrapol, and etomidate are competitive inhibitors of 11-deoxycorticosterone hydroxylation by 11 beta-hydroxylase. [H-3]Metyrapol and 4- [I-131]iodometomidate bind with high affinity to membranes prepared from bovine and rat adrenals. Here we report inhibitory potencies of several compounds structurally related to one or both of these adrenostatic drugs, against the binding of both radioligands to rat adrenal membranes. While derivatives of etomidate inhibited the binding of both radioligands with similar potencies, derivatives of metyrapone inhibited the binding of 4-[I-131]iodometomidate about 10 times weaker than the binding of [H-3]metyrapol. By X-ray structure analysis the absolute configuration of (+)-1-(2-fluorophenyl)-2-methyl-2-(pyridin-3-yl)-1-propanol [(+)-11, a derivative of metyrapol] was established as (R). We introduce 1-(2-fluorophenyl)-2-methyl-2-(pyridin-3-yl)-1-propanone (9; K-i = 6 nM), 2-(1-imidazolyl)-2-methyl-1-phenyl-1-propanone (13; 2 nM), and (R)-(+)-[1-(4-iodophenyl)ethyl]-1H-imidazole (34; 4 nM) as new high affinity ligands for the metyrapol binding site on 11 beta-hydroxylase and discuss our results in relation to a proposed active site model of 11 beta-hydroxylase.

  DOI：

  10.1021/mp3006227
• 作为产物：
  描述：

  1-(2-fluorophenyl)-2-methyl-2-(pyridin-3-yl)-1-propanone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以79%的产率得到(±)-1-(2-fluorophenyl)-2-methyl-2-(pyridin-3-yl)-1-propanol
  参考文献：
  名称：

  [³H]Metyrapol and 4-[¹³¹I]Iodometomidate Label Overlapping, but Not Identical, Binding Sites on Rat Adrenal Membranes

  摘要：

  Metyrapone, metyrapol, and etomidate are competitive inhibitors of 11-deoxycorticosterone hydroxylation by 11 beta-hydroxylase. [H-3]Metyrapol and 4- [I-131]iodometomidate bind with high affinity to membranes prepared from bovine and rat adrenals. Here we report inhibitory potencies of several compounds structurally related to one or both of these adrenostatic drugs, against the binding of both radioligands to rat adrenal membranes. While derivatives of etomidate inhibited the binding of both radioligands with similar potencies, derivatives of metyrapone inhibited the binding of 4-[I-131]iodometomidate about 10 times weaker than the binding of [H-3]metyrapol. By X-ray structure analysis the absolute configuration of (+)-1-(2-fluorophenyl)-2-methyl-2-(pyridin-3-yl)-1-propanol [(+)-11, a derivative of metyrapol] was established as (R). We introduce 1-(2-fluorophenyl)-2-methyl-2-(pyridin-3-yl)-1-propanone (9; K-i = 6 nM), 2-(1-imidazolyl)-2-methyl-1-phenyl-1-propanone (13; 2 nM), and (R)-(+)-[1-(4-iodophenyl)ethyl]-1H-imidazole (34; 4 nM) as new high affinity ligands for the metyrapol binding site on 11 beta-hydroxylase and discuss our results in relation to a proposed active site model of 11 beta-hydroxylase.

  DOI：

  10.1021/mp3006227