21(S)-羟基孟鲁司特 | 184763-29-9

• 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: 21(S)-羟基孟鲁司特
• 中文别名: {1-[({(1R,3R)-1-{3-[(E)-2-(7-氯-2-喹啉基)乙烯基]苯基}-3-羟基-3-[2-(2-羟基-2-丙基)苯基]丙基}硫基)甲基]环丙基}乙酸
• 英文名称: L 772146
• 英文别名: 21(S)-Hydroxy Montelukast；2-[1-[[(1R,3S)-1-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-hydroxy-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanylmethyl]cyclopropyl]acetic acid
• CAS: 184763-29-9
• 化学式: C₃₅H₃₆ClNO₄S
• 分子量: 602.194
• InChiKey: CHRNGXJVKOMERP-SIOAQITRSA-N

物化性质

• 熔点：
  71-75°C
• 沸点：
  787.8±60.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮、氯仿

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  42
• 可旋转键数：
  12
• 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

21(S)-羟基孟鲁司特是孟鲁司特已知的人体代谢物。

21(S)-Hydroxy Montelukast is a known human metabolite of montelukast.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  甲基氯化镁 、 {1-[(R)-1-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-(3-oxo-1,3-dihydro-isobenzofuran-1-yl)-ethylsulfanylmethyl]-cyclopropyl}-acetic acid 在 cerium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以50%的产率得到{1-[({(1R,3R)-1-{3-[(E)-2-(7-氯-2-喹啉基)乙烯基]苯基}-3-羟基-3-[2-(2-羟基-2-丙基)苯基]丙基}硫基)甲基]环丙基}乙酸
  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

• US5750539A
  申请人：——

  公开号：US5750539A

  公开（公告）日：1998-05-12
• 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.