孟鲁司特1,2-二醇 | 186352-97-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 孟鲁司特1,2-二醇
• 中文别名: 孟鲁斯特1,2二醇
• 英文名称: 36-Hydroxymontelukast
• 英文别名: 1-((((1R)-1-(3-((1E)-2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1,2-dihydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetic acid；2-[1-[[(1R)-1-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-[2-(1,2-dihydroxypropan-2-yl)phenyl]propyl]sulfanylmethyl]cyclopropyl]acetic acid
• CAS: 186352-97-6
• 化学式: C₃₅H₃₆ClNO₄S
• 分子量: 602.194
• InChiKey: UFQIEVSCRCMNLW-SHISVWIYSA-N

物化性质

• 熔点：
  65-67?C
• 溶解度：
  可溶于丙酮（少许）、乙腈（少许）、乙酸乙酯（少许）、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

ADMET

代谢

Montelukast 1,2-二醇是孟鲁司特已知的人体代谢物。

Montelukast 1, 2-Diol is a known human metabolite of montelukast.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  [S-(E)]-2-[3-[3-[2-(7-氯-2-喹啉基)乙烯基]苯基]-3-羟基丙基]苯甲酸甲酯 在 lithium hydroxide 、 正丁基锂 、 4-甲基苯磺酸吡啶 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 22.5h， 生成 孟鲁司特1,2-二醇
  参考文献：
  名称：

  Synthesis of Montelukast (MK-0476) Metabolic Oxidation Products

  摘要：

  We report the chemical synthesis of six oxidized derivatives of MK-0476 (Montelukast, L-706631), which have been key tools in the identification of its metabolites. We have prepared three diastereoisomeric pairs of potential oxidative metabolites of MK-0476, starting from the (S)-hydroxy ester 7 in 10 and five steps, and starting from MK-0476 itself in one step. The key benzylic hydroxyl of 1 and 2 was introduced by a bromination and saponification reaction sequence. In the case of the hydroxyl of 3 and 4, the key step was the addition of a hydroxymethyl carbanion equivalent on ketone 20. The two sulfoxide 5 and 6 were prepared by a direct oxidation of MK-0476 with m-chloroperbenzoic acid.

  DOI：

  10.1021/jo9615817

文献信息

• Synthesis of Montelukast (MK-0476) Metabolic Oxidation Products
  作者：Claude Dufresne、Michel Gallant、Yves Gareau、Réjean Ruel、Laird Trimble、Marc Labelle

  DOI：10.1021/jo9615817

  日期：1996.1.1

  We report the chemical synthesis of six oxidized derivatives of MK-0476 (Montelukast, L-706631), which have been key tools in the identification of its metabolites. We have prepared three diastereoisomeric pairs of potential oxidative metabolites of MK-0476, starting from the (S)-hydroxy ester 7 in 10 and five steps, and starting from MK-0476 itself in one step. The key benzylic hydroxyl of 1 and 2 was introduced by a bromination and saponification reaction sequence. In the case of the hydroxyl of 3 and 4, the key step was the addition of a hydroxymethyl carbanion equivalent on ketone 20. The two sulfoxide 5 and 6 were prepared by a direct oxidation of MK-0476 with m-chloroperbenzoic acid.