S,S'-bis-benzyl-N,N'-bis-benzyloxycarbonyl ethylene bis-L-β-homocysteine | 246039-26-9

• 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: S,S'-bis-benzyl-N,N'-bis-benzyloxycarbonyl ethylene bis-L-β-homocysteine
• 英文别名: (3R)-4-benzylsulfanyl-3-[2-[[(2R)-1-benzylsulfanyl-3-carboxypropan-2-yl]-phenylmethoxycarbonylamino]ethyl-phenylmethoxycarbonylamino]butanoic acid
• CAS: 246039-26-9
• 化学式: C₄₀H₄₄N₂O₈S₂
• 分子量: 744.93
• InChiKey: MHEQWEGSCYABGT-LQFQNGICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  52
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  184
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  S,S'-bis-benzyl-N,N'-bis-benzyloxycarbonyl ethylene bis-L-β-homocysteine 在 氨 、 sodium 作用下， 以1.8 g的产率得到ethylene bis-L-β-homocysteine
  参考文献：
  名称：

  Synthesis and evaluation of β-homocysteine derivatives of99mTc-L,L-EC and99mTc-L,L-ECD

  摘要：

  Bis-amine bis-thiol tetraligands such as ethylene dicysteine (EC) and its diethylester (ECD) bind Tc-99m efficiently at room temperature and neutral to alkaline pH to form stable complexes. The use of bis-amine bis-thiol ligands as bifunctional chelating agents (BCAs) for labelling of bioactive compounds (peptides, diphosphonates, etc.) looks promising. To study the effect of extending the carboxylic side-group in Tc-99m-L,L-EC and Tc-99m-L,L-ECD, we have synthesised ethylene bis-L-beta-homocysteine (L,L-EC) and its diethylester derivative L,L-EhCD, incorporating a methylene group between each of the carboxyl groups and the N2S2 tetraligand core. The more distant carboxyl groups could offer reduced steric hindrance in the use of L,L-EhC and L,L-EhCD as BCAs.

  DOI：

  10.1002/(sici)1099-1344(199907)42:7<683::aid-jlcr230>3.0.co;2-0
• 作为产物：
  描述：

  N,N'-乙基二-L-半胱氨酸 在 N-甲基吗啉 、 sodium hydroxide 、 silver benzoate 、 sodium 、 sodium carbonate 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 氨 、 水 为溶剂， 反应 19.83h， 生成 S,S'-bis-benzyl-N,N'-bis-benzyloxycarbonyl ethylene bis-L-β-homocysteine
  参考文献：
  名称：

  Synthesis and evaluation of β-homocysteine derivatives of99mTc-L,L-EC and99mTc-L,L-ECD

  摘要：

  Bis-amine bis-thiol tetraligands such as ethylene dicysteine (EC) and its diethylester (ECD) bind Tc-99m efficiently at room temperature and neutral to alkaline pH to form stable complexes. The use of bis-amine bis-thiol ligands as bifunctional chelating agents (BCAs) for labelling of bioactive compounds (peptides, diphosphonates, etc.) looks promising. To study the effect of extending the carboxylic side-group in Tc-99m-L,L-EC and Tc-99m-L,L-ECD, we have synthesised ethylene bis-L-beta-homocysteine (L,L-EC) and its diethylester derivative L,L-EhCD, incorporating a methylene group between each of the carboxyl groups and the N2S2 tetraligand core. The more distant carboxyl groups could offer reduced steric hindrance in the use of L,L-EhC and L,L-EhCD as BCAs.

  DOI：

  10.1002/(sici)1099-1344(199907)42:7<683::aid-jlcr230>3.0.co;2-0

文献信息

• Synthesis and evaluation of β-homocysteine derivatives of99mTc-L,L-EC and99mTc-L,L-ECD
  作者：K. O. Mang'Era、A. Verbruggen

  DOI：10.1002/(sici)1099-1344(199907)42:7<683::aid-jlcr230>3.0.co;2-0

  日期：1999.7

  Bis-amine bis-thiol tetraligands such as ethylene dicysteine (EC) and its diethylester (ECD) bind Tc-99m efficiently at room temperature and neutral to alkaline pH to form stable complexes. The use of bis-amine bis-thiol ligands as bifunctional chelating agents (BCAs) for labelling of bioactive compounds (peptides, diphosphonates, etc.) looks promising. To study the effect of extending the carboxylic side-group in Tc-99m-L,L-EC and Tc-99m-L,L-ECD, we have synthesised ethylene bis-L-beta-homocysteine (L,L-EC) and its diethylester derivative L,L-EhCD, incorporating a methylene group between each of the carboxyl groups and the N2S2 tetraligand core. The more distant carboxyl groups could offer reduced steric hindrance in the use of L,L-EhC and L,L-EhCD as BCAs.