N-乙酰基-S-[N-(2-苯基乙基)硫代氨基甲酰]-L-半胱氨酸 | 131918-97-3

• 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
• 中文名称: N-乙酰基-S-[N-(2-苯基乙基)硫代氨基甲酰]-L-半胱氨酸
• 英文名称: N-acetyl-S-[N-(2-phenylethyl)thiocarbamoyl]-L-cysteine
• 英文别名: phenethyl isothiocyanate N-acetylcysteine conjugate；N-Acetyl-S-(N-Phenylethylthiocarbamoyl)cysteine；phenethyl thiocarbamoylmercapturate；PEITC-NAC；(2R)-2-acetamido-3-(2-phenylethylcarbamothioylsulfanyl)propanoic acid
• CAS: 131918-97-3
• 化学式: C₁₄H₁₈N₂O₃S₂
• 分子量: 326.441
• InChiKey: BPWJNEDSCLPNGK-LBPRGKRZSA-N

物化性质

• 熔点：
  55-58°C
• 溶解度：
  可溶于氯仿、DMSO、甲醇（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-半胱氨酸 、 N-乙酰基-S-[N-(2-苯基乙基)硫代氨基甲酰]-L-半胱氨酸 反应 3.33h， 生成 S-（N-苯乙硫代氨基甲酰基）-L-半胱氨酸
  参考文献：
  名称：

  Inhibition of N-Nitrosodimethylamine Demethylase in Rat and Human Liver Microsomes by Isothiocyanates and Their Glutathione, l-Cysteine, and N-Acetyl-l-cysteine Conjugates¹

  摘要：

  Natural and synthetic isothiocyanates and their conjugates were examined for their inhibitory effects toward rat and human liver microsomal N-dimethylnitrosoamine demethylase (NDMAd) activity using a radiometric NDMAd assay. Substrate concentrations of 30 and 60 mu M were used to probe the activity of cytochrome P4502E1 isozyme through the a-hydroxylation of NDMA. It was found that alkyl isothiocyanates such as sulforaphane and allyl isothiocyanate displayed very weak inhibition, whereas the arylalkyl isothiocyanates such as benzyl and phenethyl isothiocyanate showed significant inhibition toward rat liver NDMAd activity with IC50 values of 9.0 and 8.3,mu M, respectively. More interestingly, glutathione conjugates of benzyl, phenethyl, and 6-phenylhexyl isothiocyanates all inhibited NDMAd at the comparable concentrations. In the phenethyl isothiocyanate conjugates series, there exist marked differences in their inhibitory activity; i.e., its conjugates with L-cysteine (IC50 = 4.3 mu M) and with glutathione (IC50 = 4.0 mu M) are more potent than its conjugate of N-acetylcysteine (IC50 = 24.0 mu M). The same trend was also observed for the human liver microsomal NDMAd activity. The half-lives of these conjugates were determined in the presence of other free thiols from L-cysteine or glutathione using an HPLC system. It was shown that isothiocyanates are released from their conjugates and react with the free thiols present in the solution. The longer half-life of N-acetylcysteine conjugate of phenethyl isothiocyanate as compared to the other conjugates is consistent with its lower inhibitory activity. The inhibition of NDMAd, and therefore cytochrome P4502E1, by isothiocyanate conjugates is most likely due to the action of the free isothiocyanates released from the conjugates. Since cytochrome P4502E1 and other isozymes play important roles in the activation of the tobacco-specific nitrosoamines, these results provide a basis for investigating the potential of isothiocyanate conjugates as chemopreventive agents.

  DOI：

  10.1021/tx9502094
• 作为产物：
  描述：

  N-乙酰-L-半胱氨酸 、 2-苯基乙基异硫代氰酸酯 在 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 以72.8%的产率得到N-乙酰基-S-[N-(2-苯基乙基)硫代氨基甲酰]-L-半胱氨酸
  参考文献：
  名称：

  Synthesis of isothiocyanate-derived mercapturic acids

  摘要：

  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.

  DOI：

  10.1016/s0223-5234(03)00141-7

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.
• Inhibition of human leukaemia 60 cell growth by mercapturic acid metabolites of phenylethyl isothiocyanate
  作者：A. Adesida、L.G. Edwards、P.J. Thornalley

  DOI：10.1016/0278-6915(96)00124-x

  日期：1996.4

  Mercapturic acid pathway metabolites of phenylethyl isothiocyanate inhibited the growth of human leukaemia 60 (HL60) cells in vitro. The adduct with L-cysteine, S-(N-phenylethylthiocarbamoyl)cysteine, was the most potent with strong antileukaemic activity: the median growth inhibitory concentration (GC(50)) value was 336 +/- 1 nM (N = 18) compared with GC(50) values of the precursor formed from dietary glucosinolates, phenylethyl isothiocyanate, 1.49 +/- 0.01 mu M (N = 8), and the initial mercapturic acid pathway metabolite S-(N-phenylethylthiocarbamoyl)glutathion 5.46 +/- 0.36 mu M (N = 18). S-(N-Benzylthiocarbamoyl)cysteine and S-(N-phenylpropylthiocarbamoyl)cysteine also had antiproliferative activity but S-(N-phenylethylthiocarbamoyl)cysteine was the most potent compound studied. The latter induced DNA fragmentation in HL60 cells but DNA laddering characteristic of apoptosis was not observed. It had low toxicity to corresponding differentiated cells, neutrophils, in culture, and therefore the cytotoxicity had selectivity for leukaemia cells. The antiproliferative activity of S-(N-phenylethylthiocarbamoyl)cysteine was lost during preincubation with culture medium, attributed to S-thiocarbamoyl transfer to serum proteins, which may decrease its effectiveness in vivo. The antiproliferative activity of S-(N-phenylalkylthiocarbamoyl)cysteine derivatives, by inhibiting tumour growth in pre-clinical development, may contribute to the association of decreased cancer incidence with dietary glucosinolate consumption. (C) 1996 Elsevier Science Ltd. All rights reserved.
• US20140274965A1
  申请人：——

  公开号：US20140274965A1

  公开（公告）日：2014-09-18
• US20140274966A1
  申请人：——

  公开号：US20140274966A1

  公开（公告）日：2014-09-18
• Drink Product and Use Thereof
  申请人：HYGIA PHARMACEUTICALS, LLC

  公开号：US20160030455A1

  公开（公告）日：2016-02-04

  A drink product having pharmaceutical compositions as an active ingredients of at least one phosphorylated inositol, optionally Genistein, optionally Ubiquinol, and optionally additional unphosphorylated inositol. Uses for prevention, treatment, and reduction in risk of developing or progression of a number of conditions are disclosed. This invention relates to certain drink products that generally are aqueous solutions containing Genistein (optionally), at least one phosphorylated myoinositol having 1 to 9 phosphate groups (and/or any of the optical isomers thereof) optionally enriched with any or all of myoinositol, optical isomers of myoinositol, electrolytes, flavors, vitamins, free radical scavengers, and sweeteners.