N-methyl-N-<2-(methylamino)ethyl>carbamic acid 4-methoxyphenyl ester hydrochloride | 122734-28-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-methyl-N-<2-(methylamino)ethyl>carbamic acid 4-methoxyphenyl ester hydrochloride
• 英文别名: N-methyl-N-[2-(methylamino)ethyl]carbamic acid 4-methoxyphenyl ester hydrochloride；(4-methoxyphenyl) N-methyl-N-[2-(methylamino)ethyl]carbamate;hydrochloride
• CAS: 122734-28-5
• 化学式: C₁₂H₁₈N₂O₃*ClH
• 分子量: 274.747
• InChiKey: KGFFZFUOAYFDDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  50.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-N-<2-(methylamino)ethyl>carbamic acid 4-methoxyphenyl ester hydrochloride 在 phosphate buffer pH 7.4 作用下， 反应 6.5h， 以14.4%的产率得到1,3-二甲基-2-咪唑啉酮
  参考文献：
  名称：

  Cyclization-activated prodrugs. Basic carbamates of 4-hydroxyanisole

  摘要：

  A series of basic carbamates of 4-hydroxyanisole was prepared and evaluated as progenitors of this melanocytotoxic phenol. All of the carbamates were relatively stable at low pH but released 4-hydroxyanisole cleanly at pH 7.4 at rates that were structure dependent. A detailed study of the N-methyl-N-[2-(methylamino)ethyl]carbamate showed that generation of the parent phenol followed first-order kinetics with t1/2 = 36.3 min at pH 7.4, 37 degrees C, and was accompanied by formation of N,N'-dimethylimidazolidinone. These basic carbamates are examples of cyclization-activated prodrugs in which generation of the active drug is not linked to enzymatic cleavage but rather depends solely upon a predictable, intramolecular cyclization-elimination reaction.

  DOI：

  10.1021/jm00163a016
• 作为产物：
  描述：

  氯甲酸4-甲氧基苯酯 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 23.0h， 生成 N-methyl-N-<2-(methylamino)ethyl>carbamic acid 4-methoxyphenyl ester hydrochloride
  参考文献：
  名称：

  Cyclization-activated prodrugs. Basic carbamates of 4-hydroxyanisole

  摘要：

  A series of basic carbamates of 4-hydroxyanisole was prepared and evaluated as progenitors of this melanocytotoxic phenol. All of the carbamates were relatively stable at low pH but released 4-hydroxyanisole cleanly at pH 7.4 at rates that were structure dependent. A detailed study of the N-methyl-N-[2-(methylamino)ethyl]carbamate showed that generation of the parent phenol followed first-order kinetics with t1/2 = 36.3 min at pH 7.4, 37 degrees C, and was accompanied by formation of N,N'-dimethylimidazolidinone. These basic carbamates are examples of cyclization-activated prodrugs in which generation of the active drug is not linked to enzymatic cleavage but rather depends solely upon a predictable, intramolecular cyclization-elimination reaction.

  DOI：

  10.1021/jm00163a016

文献信息

• Carbamates of 4-hydroxyanisole as prodrugs for chemotherapy of melanoma
  申请人：Merck & Co., Inc.

  公开号：EP0296811A2

  公开（公告）日：1988-12-28

  Derivatives of 4-hydroxyanisole carbamate are suitable as prodrugs for the delivery and concentration of 4-hydroxyanisole in melanomas.

  4-hydroxyanisole carbamate 的衍生物适合作为原药，用于在黑色素瘤中输送和浓缩 4-hydroxyanisole 。
• JP1026547A
  申请人：——

  公开号：JP1026547A

  公开（公告）日：1989-01-27
• US4812590A
  申请人：——

  公开号：US4812590A

  公开（公告）日：1989-03-14
• Cyclization-activated prodrugs. Basic carbamates of 4-hydroxyanisole
  作者：Walfred S. Saari、John E. Schwering、Paulette A. Lyle、Steven J. Smith、Edward L. Engelhardt

  DOI：10.1021/jm00163a016

  日期：1990.1

  A series of basic carbamates of 4-hydroxyanisole was prepared and evaluated as progenitors of this melanocytotoxic phenol. All of the carbamates were relatively stable at low pH but released 4-hydroxyanisole cleanly at pH 7.4 at rates that were structure dependent. A detailed study of the N-methyl-N-[2-(methylamino)ethyl]carbamate showed that generation of the parent phenol followed first-order kinetics with t1/2 = 36.3 min at pH 7.4, 37 degrees C, and was accompanied by formation of N,N'-dimethylimidazolidinone. These basic carbamates are examples of cyclization-activated prodrugs in which generation of the active drug is not linked to enzymatic cleavage but rather depends solely upon a predictable, intramolecular cyclization-elimination reaction.