2-(Acetylsulfanylmethyl)-3-cyclohexylpropanoic acid | 89022-01-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(Acetylsulfanylmethyl)-3-cyclohexylpropanoic acid
• CAS: 89022-01-5
• 化学式: C₁₂H₂₀O₃S
• 分子量: 244.355
• InChiKey: OHIATIAHIMTYJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(Acetylsulfanylmethyl)-3-cyclohexylpropanoic acid 在 吡啶 、 lithium hydroxide 、 草酰氯 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (4S)-4-(2-cyclohexylmethyl-3-mercaptopropionylamino)-4-(N-phenylcarbamoyl)-butyric acid
  参考文献：
  名称：

  New orally active enkephalinase inhibitors: their synthesis, biological activity, and analgesic properties

  摘要：

  A series of (4S)-4-[(2S)-benzyl-3-mercaptopropionylamino]-4-(N-phenylcarbamoyl)-butyric acids has been identified as potent systemically active enkephalinase inhibitors. Structure-activity relationships (SAR) are discussed. Further chemical modification of the inhibitors was carried out in order to identify the inhibitors which are orally active in an animal model. Compounds of particular interest are the prodrug-like analogues, including 5b (ONO-9902). Their analgesic effects after oral administration were evaluated. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10048-7
• 作为产物：
  描述：

  ethyl 2-(cyclohexylmethyl)acrylate 在 氢氧化钾 作用下， 以 乙醇 、 苯 为溶剂， 反应 3.5h， 生成 2-(Acetylsulfanylmethyl)-3-cyclohexylpropanoic acid
  参考文献：
  名称：

  New orally active enkephalinase inhibitors: their synthesis, biological activity, and analgesic properties

  摘要：

  A series of (4S)-4-[(2S)-benzyl-3-mercaptopropionylamino]-4-(N-phenylcarbamoyl)-butyric acids has been identified as potent systemically active enkephalinase inhibitors. Structure-activity relationships (SAR) are discussed. Further chemical modification of the inhibitors was carried out in order to identify the inhibitors which are orally active in an animal model. Compounds of particular interest are the prodrug-like analogues, including 5b (ONO-9902). Their analgesic effects after oral administration were evaluated. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10048-7

文献信息

• Hydantoin derivative as metalloprotease inhibitor
  申请人：FUJIREBIO INC.

  公开号：EP0640594A1

  公开（公告）日：1995-03-01

  A hydantoin derivative represented by formula (I): wherein the all symbols are defined in the disclosure. The hydantoin derivative has an inhibitory activity on metalloprotease and hence is useful as analgesic and cardiovascular drug.

  一种以化学式(I)表示的噻唑烷酮衍生物：其中所有符号均在披露中定义。该噻唑烷酮衍生物具有对金属蛋白酶的抑制活性，因此可用作镇痛和心血管药物。
• New orally active enkephalinase inhibitors: their synthesis, biological activity, and analgesic properties
  作者：Kazuhiko Senokuchi、Hisao Nakai、Yuuki Nagao、Yasuhiro Sakai、Nobuo Katsube、Masanori Kawamura

  DOI：10.1016/s0968-0896(97)10048-7

  日期：1998.4

  A series of (4S)-4-[(2S)-benzyl-3-mercaptopropionylamino]-4-(N-phenylcarbamoyl)-butyric acids has been identified as potent systemically active enkephalinase inhibitors. Structure-activity relationships (SAR) are discussed. Further chemical modification of the inhibitors was carried out in order to identify the inhibitors which are orally active in an animal model. Compounds of particular interest are the prodrug-like analogues, including 5b (ONO-9902). Their analgesic effects after oral administration were evaluated. (C) 1998 Elsevier Science Ltd. All rights reserved.