3-[4-nitrophenoxycarbonyl]-1-(4-aminocarbonylphenyl)-3-methyltriazene | 1407791-46-1

• 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: 3-[4-nitrophenoxycarbonyl]-1-(4-aminocarbonylphenyl)-3-methyltriazene
• 英文别名: (4-nitrophenyl) N-[(4-carbamoylphenyl)diazenyl]-N-methylcarbamate
• CAS: 1407791-46-1
• 化学式: C₁₅H₁₃N₅O₅
• 分子量: 343.299
• InChiKey: BQDQCNXAMALPCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  143
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-[4-nitrophenoxycarbonyl]-1-(4-aminocarbonylphenyl)-3-methyltriazene 、 L-谷氨酸二叔丁酯盐酸盐 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以100%的产率得到ditert-butyl (2S)-2-[[[(4-carbamoylphenyl)diazenyl]-methylcarbamoyl]amino]pentanedioate
  参考文献：
  名称：

  Development of triazene prodrugs for ADEPT strategy: New insights into drug delivery system based on carboxypeptidase G2 activation

  摘要：

  Six novel urea triazene prodrugs have been synthesized to apply in antibody-directed enzyme prodrug therapy (ADEPT). The chemical and plasmatic stability of L-glutamate triazene prodrugs were evaluated and the chemical reactivity was mainly attributed to an intramolecular catalysis promoted by the neighbouring carboxylate group of the glutamic moiety. These prodrugs showed an elevated binding to plasma proteins. The L-glutamate triazenes were evaluated as prodrugs of the alkylating agent's monomethyltriazenes, by activation of the bacterial enzyme carboxypeptidase G2 (CPG2). The synthesized prodrugs have been shown to be good substrates for CPG2, and therefore new candidates for ADEPT strategy. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.029
• 作为产物：
  描述：

  (2S)-2-[[[(4-carbamoylphenyl)diazenyl]-methylcarbamoyl]amino]pentanedioic acid 在 吡啶 、 Pseudomonas sp. E_.C_. 3.4.17.11 carboxypeptidase G₂ 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 3-[4-nitrophenoxycarbonyl]-1-(4-aminocarbonylphenyl)-3-methyltriazene
  参考文献：
  名称：

  Development of triazene prodrugs for ADEPT strategy: New insights into drug delivery system based on carboxypeptidase G2 activation

  摘要：

  Six novel urea triazene prodrugs have been synthesized to apply in antibody-directed enzyme prodrug therapy (ADEPT). The chemical and plasmatic stability of L-glutamate triazene prodrugs were evaluated and the chemical reactivity was mainly attributed to an intramolecular catalysis promoted by the neighbouring carboxylate group of the glutamic moiety. These prodrugs showed an elevated binding to plasma proteins. The L-glutamate triazenes were evaluated as prodrugs of the alkylating agent's monomethyltriazenes, by activation of the bacterial enzyme carboxypeptidase G2 (CPG2). The synthesized prodrugs have been shown to be good substrates for CPG2, and therefore new candidates for ADEPT strategy. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.029