N-phenethyl 3-mercaptopropionamide | 102337-31-5

• 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: N-phenethyl 3-mercaptopropionamide
• 英文别名: N-(2-phenylethyl)-3-sulfanylpropanamide
• CAS: 102337-31-5
• 化学式: C₁₁H₁₅NOS
• 分子量: 209.312
• InChiKey: WDPJGDDBQSGLTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  30.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-phenethyl 3-mercaptopropionamide 在 sodium hydroxide 、 TEMPO oxoammonium ion 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以66%的产率得到3,3'-disulfanediylbis(N-phenethylpropanamide)
  参考文献：
  名称：

  Important Role of the 3-Mercaptopropionamide Moiety in Glutathione:  Promoting Effect on Decomposition of the Adduct of Glutathione with the Oxoammonium Ion of TEMPO

  摘要：

  Cyclic voltammetry of TEMPO in aqueous 0.1 M NaOH in the presence of glutathione (GSH) or cysteine (Cys) indicated the following points: (i) Both of the thiols rapidly formed adducts 3 with oxoammonium ion 1 anodically generated from TEMPO. (ii) 3 generated from GSH entered a succeeding reaction that generated N-oxide anion 2(-) (the reduced TEMPO). (iii) 3 produced from Cys remained intact over the time scale of voltammetry. A structural feature of GSH was considered to contribute to the observed behavior of this tripeptide. Possible structural features were evaluated by screening various thiols on the basis of whether they provided GSH-like voltammetric results. The 3-mercaptopropionamide group with an amide hydrogen in GSH was determined to be responsible for the observed difference between GSH and Cys. The likely function is to transform 3 from GSH into a 5-imino-1,2-oxathiolane intermediate, thereby releasing 2(-). Product analysis for reactions of model thiols representing GSH and Cys with 1 provided support for this argument and suggested that the reaction of GSH or Cys with 1 would produce the corresponding disulfides, regardless of whether a five-membered ring intermediate was formed. The proposed function of the 3-mercaptopropionamide moiety of GSH may provide useful insight for the molecular design of exogenous thiol compounds as novel drugs for the treatment of GSH-depletion-related disorders.

  DOI：

  10.1021/jo050783c
• 作为产物：
  描述：

  2-苯乙胺盐酸盐 在 sodium hydroxide 、 potassium carbonate 作用下， 生成 N-phenethyl 3-mercaptopropionamide
  参考文献：
  名称：

  Important Role of the 3-Mercaptopropionamide Moiety in Glutathione:  Promoting Effect on Decomposition of the Adduct of Glutathione with the Oxoammonium Ion of TEMPO

  摘要：

  Cyclic voltammetry of TEMPO in aqueous 0.1 M NaOH in the presence of glutathione (GSH) or cysteine (Cys) indicated the following points: (i) Both of the thiols rapidly formed adducts 3 with oxoammonium ion 1 anodically generated from TEMPO. (ii) 3 generated from GSH entered a succeeding reaction that generated N-oxide anion 2(-) (the reduced TEMPO). (iii) 3 produced from Cys remained intact over the time scale of voltammetry. A structural feature of GSH was considered to contribute to the observed behavior of this tripeptide. Possible structural features were evaluated by screening various thiols on the basis of whether they provided GSH-like voltammetric results. The 3-mercaptopropionamide group with an amide hydrogen in GSH was determined to be responsible for the observed difference between GSH and Cys. The likely function is to transform 3 from GSH into a 5-imino-1,2-oxathiolane intermediate, thereby releasing 2(-). Product analysis for reactions of model thiols representing GSH and Cys with 1 provided support for this argument and suggested that the reaction of GSH or Cys with 1 would produce the corresponding disulfides, regardless of whether a five-membered ring intermediate was formed. The proposed function of the 3-mercaptopropionamide moiety of GSH may provide useful insight for the molecular design of exogenous thiol compounds as novel drugs for the treatment of GSH-depletion-related disorders.

  DOI：

  10.1021/jo050783c

文献信息

• Nouveaux dérivés de l'w-mercaptopropanamide et leurs sels, leur préparation, leur application comme médicaments et les compositions les renfermant
  申请人：ROUSSEL-UCLAF

  公开号：EP0159254A1

  公开（公告）日：1985-10-23

  L'invention concerne des produits de formule (I): dans laquelle R1=H ou R'1 étant soit alcoyle, soit aryle éventuellement substitué, n=1 à 5, R2=H, alcoyle, aryle ou arylalcoyle éventuellement substitué, m=0 à 5, R3 représente: - un radical cyclique saturé (3 à 12 carbones), éventuellement accolé à phényle, R3 étant différent de cyclohexyle si R2=R1=H, m=0 et n=1; - un radical phényle éventuellement substitué, éventuellement accolé un radical cyclique saturé (5 à 9 carbones); - un radical hétérocyclique éventuellement substitué par un radical alcoyle, m ne pouvant être égal à 0 pour les valeurs phényle et hétérocycliques de R3. - un radical pyridinyle substitué par un aralcoyle, étant entendu que lorsque m=1 et n=1 et R2=R,=H ou R2=CH3 et R3 n'est pas phényle et leurs sels d'addition avec les acides, leur préparation, leur application comme médicaments et les compositions les renfermant.

  本发明涉及式 (I) 的产品： 其中 R1=H 或 R'1为烷基或任选取代的芳基，n=1至5，R2=H，任选取代的烷基、芳基或芳烷基，m=0至5，R3代表： - 饱和环基（3 至 12 个碳原子），可选择与苯基融合，如果 R2=R1=H, m=0 和 n=1 时，R3 不是环己基； - 一个任选取代的苯基，任选与一个饱和环基（5 至 9 个碳原子）融合； - 任选被烷基取代的杂环基，对于 R3 的苯基和杂环基值，m 不可能等于 0。 - 被芳烷基取代的吡啶基，不言而喻，当 m=1 和 n=1 且 R2=R,=H 或 R2=CH3 且 R3不是苯基时，以及它们与酸的加成盐、它们的制备、它们作为药物的用途和含有它们的组合物。
• Important Role of the 3-Mercaptopropionamide Moiety in Glutathione:  Promoting Effect on Decomposition of the Adduct of Glutathione with the Oxoammonium Ion of TEMPO
  作者：Hatsuo Maeda、Hong-Yan Wu、Yuji Yamauchi、Hidenobu Ohmori

  DOI：10.1021/jo050783c

  日期：2005.10.1

  Cyclic voltammetry of TEMPO in aqueous 0.1 M NaOH in the presence of glutathione (GSH) or cysteine (Cys) indicated the following points: (i) Both of the thiols rapidly formed adducts 3 with oxoammonium ion 1 anodically generated from TEMPO. (ii) 3 generated from GSH entered a succeeding reaction that generated N-oxide anion 2(-) (the reduced TEMPO). (iii) 3 produced from Cys remained intact over the time scale of voltammetry. A structural feature of GSH was considered to contribute to the observed behavior of this tripeptide. Possible structural features were evaluated by screening various thiols on the basis of whether they provided GSH-like voltammetric results. The 3-mercaptopropionamide group with an amide hydrogen in GSH was determined to be responsible for the observed difference between GSH and Cys. The likely function is to transform 3 from GSH into a 5-imino-1,2-oxathiolane intermediate, thereby releasing 2(-). Product analysis for reactions of model thiols representing GSH and Cys with 1 provided support for this argument and suggested that the reaction of GSH or Cys with 1 would produce the corresponding disulfides, regardless of whether a five-membered ring intermediate was formed. The proposed function of the 3-mercaptopropionamide moiety of GSH may provide useful insight for the molecular design of exogenous thiol compounds as novel drugs for the treatment of GSH-depletion-related disorders.