2-(Aziridin-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid | 653600-67-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(Aziridin-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid
• CAS: 653600-67-0
• 化学式: C₆H₈N₂O₂S
• 分子量: 172.208
• InChiKey: ZWISZLKQZPEDNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  96.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  DL-半胱氨酸 、 2-氮丙啶甲腈 以 水 为溶剂， 以11 mg的产率得到2-(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