7-methoxy-1,2-aziridinomitosene | 5047-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 7-methoxy-1,2-aziridinomitosene
• 英文别名: [(4S,6S)-11-methoxy-12-methyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),7,11-trien-8-yl]methyl carbamate
• CAS: 5047-66-5
• 化学式: C₁₅H₁₅N₃O₅
• 分子量: 317.301
• InChiKey: VCDAVHJWFBAJMB-CBAPKCEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-methoxy-1,2-aziridinomitosene 在 氨 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以20%的产率得到7-aminoaziridinomitosene
  参考文献：
  名称：

  Preparation and antitumor activity of 7-substituted 1,2-aziridinomitosenes

  摘要：

  7-Methoxy-1,2-aziridinomitosenes were prepared from mitomycin A and its N-methyl homologue by catalytic reduction followed by air oxidation. Treatment of these products with amines, including ammonia, ethylenimine, 2-methylethylenimine, propargylamine, and furfurylamine gave the corresponding 7-(substituted amino) derivatives. Screening of these compounds against P-388 leukemia in mice revealed some good activities. The more easily reduced compounds gave prolongation of life span comparable to that of mitomycin C, but their optimal doses were higher. Among these compounds, a methyl group on the aziridine nitrogen increased potency. The 7-amino derivatives, which were difficult to reduce to hydroquinones, were essentially inactive. The aziridinomitosenes were subjected to a Hansch-type analysis, but no statistically significant correlation was found.

  DOI：

  10.1021/jm00160a012
• 作为产物：
  描述：

  丝裂霉素 A 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以55%的产率得到7-methoxy-1,2-aziridinomitosene
  参考文献：
  名称：

  Preparation and antitumor activity of 7-substituted 1,2-aziridinomitosenes

  摘要：

  7-Methoxy-1,2-aziridinomitosenes were prepared from mitomycin A and its N-methyl homologue by catalytic reduction followed by air oxidation. Treatment of these products with amines, including ammonia, ethylenimine, 2-methylethylenimine, propargylamine, and furfurylamine gave the corresponding 7-(substituted amino) derivatives. Screening of these compounds against P-388 leukemia in mice revealed some good activities. The more easily reduced compounds gave prolongation of life span comparable to that of mitomycin C, but their optimal doses were higher. Among these compounds, a methyl group on the aziridine nitrogen increased potency. The 7-amino derivatives, which were difficult to reduce to hydroquinones, were essentially inactive. The aziridinomitosenes were subjected to a Hansch-type analysis, but no statistically significant correlation was found.

  DOI：

  10.1021/jm00160a012

文献信息

• Preparation and antitumor activity of 7-substituted 1,2-aziridinomitosenes
  作者：Bhashyam S. Iyengar、William A. Remers、William T. Bradner

  DOI：10.1021/jm00160a012

  日期：1986.10

  7-Methoxy-1,2-aziridinomitosenes were prepared from mitomycin A and its N-methyl homologue by catalytic reduction followed by air oxidation. Treatment of these products with amines, including ammonia, ethylenimine, 2-methylethylenimine, propargylamine, and furfurylamine gave the corresponding 7-(substituted amino) derivatives. Screening of these compounds against P-388 leukemia in mice revealed some good activities. The more easily reduced compounds gave prolongation of life span comparable to that of mitomycin C, but their optimal doses were higher. Among these compounds, a methyl group on the aziridine nitrogen increased potency. The 7-amino derivatives, which were difficult to reduce to hydroquinones, were essentially inactive. The aziridinomitosenes were subjected to a Hansch-type analysis, but no statistically significant correlation was found.