(S)-2-{Bis-[2-(bis-benzyloxycarbonylmethyl-amino)-ethyl]-amino}-3-phenyl-propionic acid benzyl ester | 199294-32-1

• 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: (S)-2-{Bis-[2-(bis-benzyloxycarbonylmethyl-amino)-ethyl]-amino}-3-phenyl-propionic acid benzyl ester
• 英文别名: benzyl (2S)-2-[bis[2-[bis(2-oxo-2-phenylmethoxyethyl)amino]ethyl]amino]-3-phenylpropanoate
• CAS: 199294-32-1
• 化学式: C₅₆H₅₉N₃O₁₀
• 分子量: 934.099
• InChiKey: XBDHNHHGRAMNEC-XHIZWQFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  69
• 可旋转键数：
  33
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (S)-2-{Bis-[2-(bis-benzyloxycarbonylmethyl-amino)-ethyl]-amino}-3-phenyl-propionic acid benzyl ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.83h， 以89%的产率得到(S)-2-{Bis-[2-(bis-carboxymethyl-amino)-ethyl]-amino}-3-phenyl-propionic acid; hydrochloride
  参考文献：
  名称：

  Effect of Stereochemistry on the Clearance Mechanism of ¹¹¹In(III)-Labeled d- or l-Benzyldiethylenetriaminepentaacetic Acid

  摘要：

  The diethylenetriaminepentaacetic acid (DTPA) derivatives L-Bn-DTPA and D-Bn-DTPA were synthesized and radiolabeled with In-111(3+). The uptake and clearance of the compounds were determined through biodistribution and excretion studies in Wistar rats. Both isomers readily cleared from the animal. The D isomer showed relatively high kidney uptake and predominately renal clearance. The L isomer showed substantial kidney and liver uptake with equal biliary and renal clearance. Clearance was also evaluated in TR- Wistar rats, which are defective in the liver canalicular multispecific organic anion transporter (cMOAT) protein. cMOAT mediates hepatobiliary clearance of many organic anions. Both compounds were excreted through the urine in TR- Wistar rats, suggesting that cMOAT is important in the clearance of the compounds from the liver.

  DOI：

  10.1021/jm970475+
• 作为产物：
  描述：

  对甲苯磺酸 在 phosphate buffer 作用下， 以 乙腈 、 苯 为溶剂， 生成 (S)-2-{Bis-[2-(bis-benzyloxycarbonylmethyl-amino)-ethyl]-amino}-3-phenyl-propionic acid benzyl ester
  参考文献：
  名称：

  Effect of Stereochemistry on the Clearance Mechanism of ¹¹¹In(III)-Labeled d- or l-Benzyldiethylenetriaminepentaacetic Acid

  摘要：

  The diethylenetriaminepentaacetic acid (DTPA) derivatives L-Bn-DTPA and D-Bn-DTPA were synthesized and radiolabeled with In-111(3+). The uptake and clearance of the compounds were determined through biodistribution and excretion studies in Wistar rats. Both isomers readily cleared from the animal. The D isomer showed relatively high kidney uptake and predominately renal clearance. The L isomer showed substantial kidney and liver uptake with equal biliary and renal clearance. Clearance was also evaluated in TR- Wistar rats, which are defective in the liver canalicular multispecific organic anion transporter (cMOAT) protein. cMOAT mediates hepatobiliary clearance of many organic anions. Both compounds were excreted through the urine in TR- Wistar rats, suggesting that cMOAT is important in the clearance of the compounds from the liver.

  DOI：

  10.1021/jm970475+