methyl 4-[3-(4,4,7,7-tetramethyl-5,6-dithia-2,9-diazacyclodecyl)-2-oxapropyl]benzoate | 257929-00-3

• 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: methyl 4-[3-(4,4,7,7-tetramethyl-5,6-dithia-2,9-diazacyclodecyl)-2-oxapropyl]benzoate
• 英文别名: Methyl 4-[(3,3,10,10-tetramethyl-1,2,5,8-dithiadiazecan-6-yl)methoxymethyl]benzoate
• CAS: 257929-00-3
• 化学式: C₂₀H₃₂N₂O₃S₂
• 分子量: 412.618
• InChiKey: PAXGFCHFWIWBRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4-[3-(4,4,7,7-tetramethyl-5,6-dithia-2,9-diazacyclodecyl)-2-oxapropyl]benzoate 在 三甲基铝 、 三(2-羰基乙基)磷盐酸盐 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 160.25h， 生成 4-[2,3-Bis-(2-mercapto-2-methyl-propylamino)-propoxymethyl]-N-(2-diethylamino-ethyl)-benzamide
  参考文献：
  名称：

  A Potential Melanoma Tracer:  Synthesis, Radiolabeling, and Biodistribution in Mice of a New Nitridotechnetium Bis(aminothiol) Derivative Pharmacomodulated by a N-(Diethylaminoethyl)benzamide

  摘要：

  Radioiodobenzamides are the best-known agents under study for the diagnosis of cutaneous melanoma and its metastases. We report the synthesis of a new BAT derivative radiopharmaceutical in which radioiodine is replaced by 99m-technetium. The cyclic intermediary methyl 4-[3-(4,4,7,7-tetramethyl-5,6-dithia-2,9-diazacyclodecyl)-2-oxapropyl]benzoate (5) occurred in two different conformations identified by spectroscopic analysis. The final BAT ligand was radiolabeled using the nitridotechnetium core by a ligand-exchange reaction. Two different complexes mere purified. After macroscopic gs-technetium synthesis, syn and anti isomers were identified. The global radiochemical yield was over 80%. The biodistribution of these two complexes was evaluated in mice bearing murine B16 melanoma. Extensive liver and kidney uptake was observed, but the benzamide tropism for the tumor was partially preserved.

  DOI：

  10.1021/jm981089a
• 作为产物：
  描述：

  methyl 4-[3-(4,4,7,7-tetramethyl-5,6-dithia-2,9-diazacyclodeca-2,8-dienyl)-2-oxapropyl]benzoate 在 盐酸 、 sodium cyanoborohydride 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 4.0h， 以57%的产率得到methyl 4-[3-(4,4,7,7-tetramethyl-5,6-dithia-2,9-diazacyclodecyl)-2-oxapropyl]benzoate
  参考文献：
  名称：

  A Potential Melanoma Tracer:  Synthesis, Radiolabeling, and Biodistribution in Mice of a New Nitridotechnetium Bis(aminothiol) Derivative Pharmacomodulated by a N-(Diethylaminoethyl)benzamide

  摘要：

  Radioiodobenzamides are the best-known agents under study for the diagnosis of cutaneous melanoma and its metastases. We report the synthesis of a new BAT derivative radiopharmaceutical in which radioiodine is replaced by 99m-technetium. The cyclic intermediary methyl 4-[3-(4,4,7,7-tetramethyl-5,6-dithia-2,9-diazacyclodecyl)-2-oxapropyl]benzoate (5) occurred in two different conformations identified by spectroscopic analysis. The final BAT ligand was radiolabeled using the nitridotechnetium core by a ligand-exchange reaction. Two different complexes mere purified. After macroscopic gs-technetium synthesis, syn and anti isomers were identified. The global radiochemical yield was over 80%. The biodistribution of these two complexes was evaluated in mice bearing murine B16 melanoma. Extensive liver and kidney uptake was observed, but the benzamide tropism for the tumor was partially preserved.

  DOI：

  10.1021/jm981089a