2-{4-(2-hydroxy-3-methoxypropoxy)phenylcarbamoyl}ethyldimethylsulfonium p-toluenesulfonate

• 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: 2-{4-(2-hydroxy-3-methoxypropoxy)phenylcarbamoyl}ethyldimethylsulfonium p-toluenesulfonate
• 英文别名: [3-[4-(2-Hydroxy-3-methoxypropoxy)anilino]-3-oxopropyl]-dimethylsulfanium;4-methylbenzenesulfonate
• 化学式: C₇H₇O₃S*C₁₅H₂₄NO₄S
• 分子量: 485.623
• InChiKey: UZGRAUUPMXSLIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-methoxy-3-(4-nitrophenoxy)propan-2-ol 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 130.0h， 生成 2-{4-(2-hydroxy-3-methoxypropoxy)phenylcarbamoyl}ethyldimethylsulfonium p-toluenesulfonate
  参考文献：
  名称：

  Synthesis and Antiallergic Activity of Dimethyl-2-(phenylcarbamoyl)ethylsulfonium p-Toluenesulfonate Derivatives

  摘要：

  The derivatives of dimethyl-2-(phenylcarbamoyl)ethylsulfonium p-toluenesulfonates were synthesized and evaluated for antiallergic activity. The 2,3-dihydroxyethoxy group was introduced to the phenyl ring from the standpoint of lipophilicity and electronic effects of substituent. The IgE-induced rat passive cutaneous anaphylaxis (PCA) was inhibited by oral administration of several substituted 2-[(4-propoxyphenyl)carbamoyl]ethyldimethylsulfonium p-toluenesulfonate derivatives. Among them (+/-)-2-[4-(3-ethoxy-2-hydroxypropoxy)phenyl]-carbamoyl]ethyldimethylsulfonium p-toluenesulfonate (1a, IPD-1151T) was found to possess considerable activity in the PCA test, and it was launched as Suplatast tosilate in Japan.

  DOI：

  10.1021/jm970285z

文献信息

• Sulfonium compounds, processes for preparing the compounds and
  申请人：Taiho Pharmaceutical Company Limited

  公开号：US04556737A1

  公开（公告）日：1985-12-03

  This invention provides novel sulfonium compounds, processes for the preparation of the sulfonium compounds, and pharmacological composition containing the sulfonium compound. The compounds of this invention are useful for treating allergy.

  这项发明提供了新型砜化合物，制备砜化合物的方法，以及含有砜化合物的药理组合物。这项发明的化合物对治疗过敏症非常有用。
• US4556737A
  申请人：——

  公开号：US4556737A

  公开（公告）日：1985-12-03
• Synthesis and Antiallergic Activity of Dimethyl-2-(phenylcarbamoyl)ethylsulfonium <i>p</i>-Toluenesulfonate Derivatives
  作者：Yukio Tada、Ichiro Yamawaki、Shuichi Ueda、Hiroshi Matsumoto、Naosuke Matsuura、Mitsugi Yasumoto、Akihide Koda、Mikio Hori

  DOI：10.1021/jm970285z

  日期：1998.8.1

  The derivatives of dimethyl-2-(phenylcarbamoyl)ethylsulfonium p-toluenesulfonates were synthesized and evaluated for antiallergic activity. The 2,3-dihydroxyethoxy group was introduced to the phenyl ring from the standpoint of lipophilicity and electronic effects of substituent. The IgE-induced rat passive cutaneous anaphylaxis (PCA) was inhibited by oral administration of several substituted 2-[(4-propoxyphenyl)carbamoyl]ethyldimethylsulfonium p-toluenesulfonate derivatives. Among them (+/-)-2-[4-(3-ethoxy-2-hydroxypropoxy)phenyl]-carbamoyl]ethyldimethylsulfonium p-toluenesulfonate (1a, IPD-1151T) was found to possess considerable activity in the PCA test, and it was launched as Suplatast tosilate in Japan.