4-{[Cyano(phenyl)methyl](methyl)amino}-4-oxobutanoic acid | 1026612-60-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-{[Cyano(phenyl)methyl](methyl)amino}-4-oxobutanoic acid
• 英文别名: 4-[[cyano(phenyl)methyl]-methylamino]-4-oxobutanoic acid
• CAS: 1026612-60-1
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: HSHFMGPBCYCONK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  81.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dihydroartemisinin 、 4-{[Cyano(phenyl)methyl](methyl)amino}-4-oxobutanoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到
  参考文献：
  名称：

  Synthesis and cytotoxicity of artemisinin derivatives containing cyanoarylmethyl group

  摘要：

  A series of 12 alpha -deoxoartemisinyl cyanoarylmethyl dicarboxylates (4a-4o), dicarboxylic acids 12 alpha -deoxoartemisinyl ester cyanoarylmethyl amide (5a-5k), and dicarboxylic acids 12 alpha -deoxoartemisinyl ester N-methylcyanoarylmethyl amide (6a-6l), showing moderate cytotoxicity against P388 and L1210 cells were prepared. They induced the significant accumulation of L1210 and P388 cells in the G1 phase of the cell cycle. This mechanism of action was quite different from that of the majority of cytotoxic compounds used in the chemotherapy of cancer. Compound 4b possessed better cytotoxicity than the other compounds. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01240-5
• 作为产物：
  描述：

  丁二酸酐 、 2-(甲基氨基)-2-苯基乙腈 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 4-{[Cyano(phenyl)methyl](methyl)amino}-4-oxobutanoic acid
  参考文献：
  名称：

  Synthesis and cytotoxicity of artemisinin derivatives containing cyanoarylmethyl group

  摘要：

  A series of 12 alpha -deoxoartemisinyl cyanoarylmethyl dicarboxylates (4a-4o), dicarboxylic acids 12 alpha -deoxoartemisinyl ester cyanoarylmethyl amide (5a-5k), and dicarboxylic acids 12 alpha -deoxoartemisinyl ester N-methylcyanoarylmethyl amide (6a-6l), showing moderate cytotoxicity against P388 and L1210 cells were prepared. They induced the significant accumulation of L1210 and P388 cells in the G1 phase of the cell cycle. This mechanism of action was quite different from that of the majority of cytotoxic compounds used in the chemotherapy of cancer. Compound 4b possessed better cytotoxicity than the other compounds. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01240-5

文献信息

• Artemisinin derivatives, method for the preparation thereof and pharmaceutical compositions containing the same
  申请人：Adir et Compagnie

  公开号：US06307068B1

  公开（公告）日：2001-10-23

  The invention relates to compound of the general formula (I): R—O—A  (I) wherein: R represents the radical of formula (II): A is as defined in the description, and medicinal products containing the same which are useful in treating or in preventing cancer.

  本发明涉及一般式(I)的化合物：R-O-A  (I)其中：R表示式(II)的基团：A如本说明书所定义，并且包含这些化合物的药物制剂可用于治疗或预防癌症。
• DERIVES DE L'ARTEMISININE, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT
  申请人：SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES

  公开号：EP1086107A1

  公开（公告）日：2001-03-28
• US6307068B1
  申请人：——

  公开号：US6307068B1

  公开（公告）日：2001-10-23
• [EN] ARTEMISININ DERIVATIVES, METHOD FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME<br/>[FR] DERIVES DE L'ARTEMISININE, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT
  申请人：SHANGHAI INSTITUTE OF MATERIA MEDICA

  公开号：WO1999065914A1

  公开（公告）日：1999-12-23

  (EN) The invention relates to compounds of the general formula (I): R - O - A, wherein R represents the radical of formula (II) and A is as defined in the description. The invention also relates to the geometric and/or optic isomers thereof and to the pharmaceutically acceptable acid or basic addition salts thereof.(FR) L'invention concerne les composés de la formule générale (I): R - O - A, dans laquelle: R représente le radical de formule (II), A est tel que défini dans la description, leurs isomères géométriques et/ou optiques, et leurs sels d'addition à un acide ou une base pharmaceutiquement acceptables.
• Synthesis and cytotoxicity of artemisinin derivatives containing cyanoarylmethyl group
  作者：Jin-Ming Wu、Feng Shan、Guang-Shao Wu、Ying Li、Jian Ding、Dong Xiao、Jia-Xian Han、Ghanem Atassi、Stéphane Leonce、Daniel-Henri Caignard、Pierre Renard

  DOI：10.1016/s0223-5234(01)01240-5

  日期：2001.5

  A series of 12 alpha -deoxoartemisinyl cyanoarylmethyl dicarboxylates (4a-4o), dicarboxylic acids 12 alpha -deoxoartemisinyl ester cyanoarylmethyl amide (5a-5k), and dicarboxylic acids 12 alpha -deoxoartemisinyl ester N-methylcyanoarylmethyl amide (6a-6l), showing moderate cytotoxicity against P388 and L1210 cells were prepared. They induced the significant accumulation of L1210 and P388 cells in the G1 phase of the cell cycle. This mechanism of action was quite different from that of the majority of cytotoxic compounds used in the chemotherapy of cancer. Compound 4b possessed better cytotoxicity than the other compounds. (C) 2001 Editions scientifiques et medicales Elsevier SAS.