2-cyano-aziridine-1-carboxylic acid anilide | 55275-64-4

• 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: 2-cyano-aziridine-1-carboxylic acid anilide
• 英文别名: 1-Phenylcarbamoyl-2-cyano-aziridin；1-Aziridinecarboxamide, 2-cyano-N-phenyl-；2-cyano-N-phenylaziridine-1-carboxamide
• CAS: 55275-64-4
• 化学式: C₁₀H₉N₃O
• 分子量: 187.201
• InChiKey: BXBIBOQGYLPODI-UHFFFAOYSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  DL-半胱氨酸 、 2-cyano-aziridine-1-carboxylic acid anilide 以 水 为溶剂， 反应 0.25h， 以10 mg的产率得到2-amino-3-[2-cyano-2-(phenylcarbamoylamino)ethyl]sulfanylpropanoic acid
  参考文献：
  名称：

  Chemical Basis for the Biological Activity of Imexon and Related Cyanoaziridines

  摘要：

  Chemical aspects of mode of action of imexon and related cyanoaziridines were studied. These compounds do not alkylate DNA nor react with the is an element of-amino groups of L-lysine, despite the presence of an aziridine ring. They do react readily with biologically important sulfhydryl compounds to give products derived from either aziridine ring opening, interaction with the cyano group of cyanoaziridines, or opening of the iminopyrrolidone ring of imexon. The products from reactions of imexon and related cyanoaziridines with thiols are not as potent as their parent compounds against tumor cells. These results are consistent with biological studies that show that the mechanism of cytotoxicity involves thiol depletion followed by oxidative stress leading to apoptosis.

  DOI：

  10.1021/jm030225v
• 作为产物：
  描述：

  2-氮丙啶甲腈 、 异氰酸苯酯 以 甲苯 为溶剂， 以71%的产率得到2-cyano-aziridine-1-carboxylic acid anilide
  参考文献：
  名称：

  Novel Antitumor 2-Cyanoaziridine-1-carboxamides

  摘要：

  A set of 20 2-cyanoaziridine-1-carboxamides was synthesized from 2-cyanoaziridine and appropriate isocyanates. These compounds were active against a variety of solid and hematological tumor cells in culture, including strains resistant to doxorubicin and mitoxantrone. Their potencies in these assays correlated with the lipophilicity of substituents. The N-phenyl derivative was more potent and equally effective to imexon, a cyclized 2-cyanoaziridine-1-carboxamide of clinical interest, against cloned fresh human tumors.

  DOI：

  10.1021/jm980600x

文献信息

• Liposomal imexon
  申请人：——

  公开号：US20030129222A1

  公开（公告）日：2003-07-10

  Disclosed are novel compositions comprising a lipid and imexon or a derivative thereof. Also disclosed are liposomal compositions comprising imexon or a derivative thereof. Methods for administrating pharmaceutically acceptable compositions comprising a lipid and imexon or a derivative thereof for the treatment of diseases, such as cancer, are also disclosed herein.

  披露了包含脂质和伊美酮或其衍生物的新型组合物。还披露了包含伊美酮或其衍生物的脂质体组合物。本文还披露了用于治疗疾病（如癌症）的含有脂质和伊美酮或其衍生物的药用合成物的管理方法。
• NOVEL CYANOAZIRIDINES FOR TREATING CANCER
  申请人：Amplimed, Inc.

  公开号：EP1027041B1

  公开（公告）日：2003-10-22
• US6297230B1
  申请人：——

  公开号：US6297230B1

  公开（公告）日：2001-10-02
• Novel Antitumor 2-Cyanoaziridine-1-carboxamides
  作者：Bhashyam S. Iyengar、Robert T. Dorr、David S. Alberts、Evan M. Hersh、Sydney E. Salmon、William A. Remers

  DOI：10.1021/jm980600x

  日期：1999.2.1

  A set of 20 2-cyanoaziridine-1-carboxamides was synthesized from 2-cyanoaziridine and appropriate isocyanates. These compounds were active against a variety of solid and hematological tumor cells in culture, including strains resistant to doxorubicin and mitoxantrone. Their potencies in these assays correlated with the lipophilicity of substituents. The N-phenyl derivative was more potent and equally effective to imexon, a cyclized 2-cyanoaziridine-1-carboxamide of clinical interest, against cloned fresh human tumors.
• Chemical Basis for the Biological Activity of Imexon and Related Cyanoaziridines
  作者：Bhashyam S. Iyengar、Robert T. Dorr、William A. Remers

  DOI：10.1021/jm030225v

  日期：2004.1.1

  Chemical aspects of mode of action of imexon and related cyanoaziridines were studied. These compounds do not alkylate DNA nor react with the is an element of-amino groups of L-lysine, despite the presence of an aziridine ring. They do react readily with biologically important sulfhydryl compounds to give products derived from either aziridine ring opening, interaction with the cyano group of cyanoaziridines, or opening of the iminopyrrolidone ring of imexon. The products from reactions of imexon and related cyanoaziridines with thiols are not as potent as their parent compounds against tumor cells. These results are consistent with biological studies that show that the mechanism of cytotoxicity involves thiol depletion followed by oxidative stress leading to apoptosis.