1-Aziridinecarboxamide, 2-cyano-N-methyl- | 70318-58-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 1-Aziridinecarboxamide, 2-cyano-N-methyl-
• 英文别名: 2-cyano-N-methylaziridine-1-carboxamide
• CAS: 70318-58-0
• 化学式: C₅H₇N₃O
• 分子量: 125.13
• InChiKey: WEQIAZAZNSPRDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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 、 1-Aziridinecarboxamide, 2-cyano-N-methyl- 以 水 为溶剂， 反应 2.0h， 生成 2-[1-(Methylcarbamoyl)aziridin-2-yl]-4,5-dihydro-1,3-thiazole-4-carboxylic 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 、 异氰酸甲酯 以 甲苯 为溶剂， 以94%的产率得到1-Aziridinecarboxamide, 2-cyano-N-methyl-
  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

• 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.