N-acetyl-S-[N-(benzyl)thiocarbamoyl]-L-cysteine

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-acetyl-S-[N-(benzyl)thiocarbamoyl]-L-cysteine
• 英文别名: N-acetyl-S-(N-benzylthiocarbamoyl)-L-cysteine；benzyl thiocarbamoylmercapturate；(2R)-2-acetamido-3-(benzylcarbamothioylsulfanyl)propanoic acid
• 化学式: C₁₃H₁₆N₂O₃S₂
• 分子量: 312.414
• InChiKey: ZWQHOOMYVUREOI-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-乙酰-L-半胱氨酸 、 异硫氰酸苯甲酯 在 碳酸氢钠 作用下， 以 水 、 异丙醇 为溶剂， 以84%的产率得到N-acetyl-S-[N-(benzyl)thiocarbamoyl]-L-cysteine
  参考文献：
  名称：

  Synthesis and biological activity of diisothiocyanate-derived mercapturic acids

  摘要：

  This Letter deals with new non-natural diisothiocyanates, their mercapturic acid derivatives-conjugated with N-acetylcysteine as well as their antiproliferative activity towards human colon cancer cell lines and their inhibitory potency towards histone deacetylase activity. The activity of analysed isothio-cyanates is not significantly different than their N-acetylcysteine conjugates. In comparison to simple mono-isothiocyanate analogues, aliphatic diisothiocyanates and their conjugates are much more active than the simple presence of two isothiocyanate functionalities could indicate. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.045

文献信息

• Synthesis of isothiocyanate-derived mercapturic acids
  作者：Martijn Vermeulen、Binne Zwanenburg、Gordon J.F Chittenden、Hans Verhagen

  DOI：10.1016/s0223-5234(03)00141-7

  日期：2003.7

  Twelve mercapturic acids derived from saturated and unsaturated aliphatic and aromatic isothiocyanates were synthesised, by adding isothiocyanate to a solution of N-acetyl-L-cysteine and sodium bicarbonate, in a typical yield of 77%. Isothiocyanates were synthesised first by adding the corresponding alkyl bromide to phthalimide potassium salt. The obtained N-alkyl-phthalimide was hydrazinolysed yielding the alkyl amine, which subsequently was reacted with thiophosgene yielding the isothiocyanate with an overall yield of 16%. Mercapturic acids in urine can serve as a biomarker of intake to determine the health promoting potential of isothiocyanates present in cruciferous vegetables. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Synthesis and biological activity of diisothiocyanate-derived mercapturic acids
  作者：Renata Grzywa、Łukasz Winiarski、Mateusz Psurski、Agata Rudnicka、Joanna Wietrzyk、Tadeusz Gajda、Józef Oleksyszyn

  DOI：10.1016/j.bmcl.2015.11.045

  日期：2016.1

  This Letter deals with new non-natural diisothiocyanates, their mercapturic acid derivatives-conjugated with N-acetylcysteine as well as their antiproliferative activity towards human colon cancer cell lines and their inhibitory potency towards histone deacetylase activity. The activity of analysed isothio-cyanates is not significantly different than their N-acetylcysteine conjugates. In comparison to simple mono-isothiocyanate analogues, aliphatic diisothiocyanates and their conjugates are much more active than the simple presence of two isothiocyanate functionalities could indicate. (C) 2015 Elsevier Ltd. All rights reserved.