S,S'-bis-trityl-N-Boc-N'-(3-hydroxypropyl)-1,2-ethanedicysteamine | 736979-79-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: S,S'-bis-trityl-N-Boc-N'-(3-hydroxypropyl)-1,2-ethanedicysteamine
• 英文别名: tert-butyl N-[2-[3-hydroxypropyl(2-tritylsulfanylethyl)amino]ethyl]-N-(2-tritylsulfanylethyl)carbamate
• CAS: 736979-79-6
• 化学式: C₅₂H₅₈N₂O₃S₂
• 分子量: 823.176
• InChiKey: NSHUSATVUZKHKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  59
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S,S'-bis-trityl-N-Boc-N'-(3-hydroxypropyl)-1,2-ethanedicysteamine 在 吡啶 、 盐酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 8-Fluoro-5-methyl-6-oxo-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid 3-{(2-mercapto-ethyl)-[2-(2-mercapto-ethylamino)-ethyl]-amino}-propyl ester
  参考文献：
  名称：

  Synthesis, radio-LC-MS analysis and biological evaluation of99mTc-techmazenil

  摘要：

  具有氟马西尼生物学特性的 99mTc 标记化合物可用于测定中风发作后的神经元活力。因此，我们通过将 Ro-15-3890（一种带有羧酸基团而不是乙酯的氟马西尼代谢物）与带有 3-羟丙基侧链 (3-羟丙基-BAT) 的双氨基双硫醇四配体偶联来进行衍生化，以实现标记含锝-99m。通过 RP-HPLC 纯化后，在“一锅”反应中对配体进行脱保护和标记，得到 Ro-15-3890 的 99mTc-BAT-丙酯 (99mTc-techmazenil)。对孤立主峰的放射 LC-MS 分析显示了预期的 99mTc-techmazenil 的分子离子质量 (608.0618)。在正常小鼠中研究了 99mTc-techmazenil 的生物分布，结果表明该示踪剂主要通过肝胆系统从血浆中清除，并且在大脑中的摄取量非常低。对小鼠脑切片的体外结合研究表明，techmazenil 不与苯二氮卓受体结合。版权所有 © 2004 约翰·威利父子有限公司

  DOI：

  10.1002/jlcr.813
• 作为产物：
  描述：

  三苯基甲醇 在 sodium 、 N,N-二异丙基乙胺 作用下， 以 氨 、 乙腈 为溶剂， 生成 S,S'-bis-trityl-N-Boc-N'-(3-hydroxypropyl)-1,2-ethanedicysteamine
  参考文献：
  名称：

  S-Trityl protection of bis-amino bis-thiol (BAT) chelator enables flexible derivatisation and facile labelling with technetium-99m

  摘要：

  We have coupled S,S'-bis-trityl N-BOC protected 1,2-ethylenedicysteamine, a bis-amino bis-thiol (BAT) tetraligand, via a propylene or ethylene spacer to several biologically active molecules including 2-nitroimidazole, desethylflumazenil, a beta-CIT analogue, glucose and 2-(2'-hydroxy-4'-aminophenyl)-1,3-benzothiazole. The conjugates were efficiently labelled with technetium-99m by consecutive heating of the S,S'-bis-trityl protected ligand in hydrochloric acid followed by neutralisation and heating in the presence of Tc-99m-tartrate. The S,S'-bis-trityl BAT chelator is an interesting synthon that allows both flexible derivatisation with various biologically active molecules and facile labelling with technetium-99m. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00224-7

文献信息

• S-Trityl protection of bis-amino bis-thiol (BAT) chelator enables flexible derivatisation and facile labelling with technetium-99m
  作者：Bernard J. Cleynhens、Guy M. Bormans、Hubert P. Vanbilloen、Dominique V. Vanderghinste、Davy M. Kieffer、Tjibbe J. de Groot、Alfons M. Verbruggen

  DOI：10.1016/s0040-4039(03)00224-7

  日期：2003.3

  We have coupled S,S'-bis-trityl N-BOC protected 1,2-ethylenedicysteamine, a bis-amino bis-thiol (BAT) tetraligand, via a propylene or ethylene spacer to several biologically active molecules including 2-nitroimidazole, desethylflumazenil, a beta-CIT analogue, glucose and 2-(2'-hydroxy-4'-aminophenyl)-1,3-benzothiazole. The conjugates were efficiently labelled with technetium-99m by consecutive heating of the S,S'-bis-trityl protected ligand in hydrochloric acid followed by neutralisation and heating in the presence of Tc-99m-tartrate. The S,S'-bis-trityl BAT chelator is an interesting synthon that allows both flexible derivatisation with various biologically active molecules and facile labelling with technetium-99m. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis, radio-LC-MS analysis and biological evaluation of99mTc-techmazenil
  作者：Davy Kieffer、Bernard Cleynhens、Kristin Verbeke、Hubert Vanbilloen、Tjibbe de Groot、Christelle Terwinghe、Alfons Verbruggen、Guy Bormans

  DOI：10.1002/jlcr.813

  日期：2004.3.15

  A 99mTc-labelled compound with the biological characteristics of flumazenil would be useful for determination of neuronal viability after the onset of a stroke. Therefore, we have derivatized Ro-15-3890 (a flumazenil metabolite bearing a carboxylic acid group instead of an ethyl ester) by coupling it with a bisamino bisthiol tetraligand bearing a 3-hydroxypropyl side chain (3-hydroxypropyl-BAT) to enable labelling with technetium-99m. After purification by RP-HPLC, the ligand was deprotected and labelled in a ‘one pot’ reaction, yielding a 99mTc-BAT-propylester of Ro-15-3890 (99mTc-techmazenil). Radio-LC-MS analysis of the isolated main peak showed the molecular ion mass (608.0618) of the expected 99mTc-techmazenil. The biodistribution of 99mTc-techmazenil was investigated in normal mice and indicated that the tracer is cleared from plasma mainly by the hepatobiliary system and shows a very low uptake in brain. In vitro binding studies on mice brain slices indicated that techmazenil does not bind to benzodiazepine receptors. Copyright © 2004 John Wiley & Sons, Ltd.

  具有氟马西尼生物学特性的 99mTc 标记化合物可用于测定中风发作后的神经元活力。因此，我们通过将 Ro-15-3890（一种带有羧酸基团而不是乙酯的氟马西尼代谢物）与带有 3-羟丙基侧链 (3-羟丙基-BAT) 的双氨基双硫醇四配体偶联来进行衍生化，以实现标记含锝-99m。通过 RP-HPLC 纯化后，在“一锅”反应中对配体进行脱保护和标记，得到 Ro-15-3890 的 99mTc-BAT-丙酯 (99mTc-techmazenil)。对孤立主峰的放射 LC-MS 分析显示了预期的 99mTc-techmazenil 的分子离子质量 (608.0618)。在正常小鼠中研究了 99mTc-techmazenil 的生物分布，结果表明该示踪剂主要通过肝胆系统从血浆中清除，并且在大脑中的摄取量非常低。对小鼠脑切片的体外结合研究表明，techmazenil 不与苯二氮卓受体结合。版权所有 © 2004 约翰·威利父子有限公司