7-N-[2-(methylamino)ethyl]mitomycin C | 185116-45-4

• 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-N-[2-(methylamino)ethyl]mitomycin C
• 英文别名: Usqojtuifiefaz-qjiicxbusa-；[(4S,6S,7R,8S)-7-methoxy-12-methyl-11-[2-(methylamino)ethylamino]-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
• CAS: 185116-45-4
• 化学式: C₁₈H₂₅N₅O₅
• 分子量: 391.427
• InChiKey: USQOJTUIFIEFAZ-QJIICXBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  7-N-[2-(methylamino)ethyl]mitomycin C 以 氘代甲醇 为溶剂， 反应 2.0h， 生成 Bzpgprvrkwtyqq-lmmkjwtmsa-
  参考文献：
  名称：

  Mitomycin Betaines:  Synthesis, Structure, and Solvolytic Reactivity

  摘要：

  7-N-[2-(Methylamino)ethyl]mitomycin C (2b) and 7-N-[2-(ethylamino)ethyl]mitomycin C (2c) underwent rapid C(8) cyclization and oxidation to generate the novel quinoxaline mitomycin betaines 5a,b, respectively. Correspondingly, treatment of mitomycin A with N-methyl-1,2-phenylenediamine gave phenazine mitomycin betaine 17. Similar spectral properties were observed for the three heteroaromatic zwitterionic compounds 5a,b, and 17. We have learned that the formation of 5a,b proceeds by initial cyclization of the terminal amine group to the mitomycin C(8) quinone carbon to generate the corresponding hemiaminal intermediate. Dissolution of 5a,b in buffered methanolic solutions (''pH'' 5.5, 7.4) at 25 degrees C did not lead to aziridine ring opening. The reactivity of 5a,b is briefly discussed in terms of their electronic structures.

  DOI：

  10.1021/jo961378b
• 作为产物：
  描述：

  丝裂霉素 A 、 N-甲基乙二胺 以 吡啶 为溶剂， 反应 1.0h， 以99%的产率得到7-N-[2-(methylamino)ethyl]mitomycin C
  参考文献：
  名称：

  Mitomycin Betaines:  Synthesis, Structure, and Solvolytic Reactivity

  摘要：

  7-N-[2-(Methylamino)ethyl]mitomycin C (2b) and 7-N-[2-(ethylamino)ethyl]mitomycin C (2c) underwent rapid C(8) cyclization and oxidation to generate the novel quinoxaline mitomycin betaines 5a,b, respectively. Correspondingly, treatment of mitomycin A with N-methyl-1,2-phenylenediamine gave phenazine mitomycin betaine 17. Similar spectral properties were observed for the three heteroaromatic zwitterionic compounds 5a,b, and 17. We have learned that the formation of 5a,b proceeds by initial cyclization of the terminal amine group to the mitomycin C(8) quinone carbon to generate the corresponding hemiaminal intermediate. Dissolution of 5a,b in buffered methanolic solutions (''pH'' 5.5, 7.4) at 25 degrees C did not lead to aziridine ring opening. The reactivity of 5a,b is briefly discussed in terms of their electronic structures.

  DOI：

  10.1021/jo961378b