5-Nitro-imidazol-4-(N-methyl)-carboxamid | 57445-42-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-Nitro-imidazol-4-(N-methyl)-carboxamid
• 英文别名: 5-nitro-1(3)H-imidazole-4-carboxylic acid methylamide；N-methyl-5-nitro-1H-imidazole-4-carboxamide
• CAS: 57445-42-8
• 化学式: C₅H₆N₄O₃
• 分子量: 170.128
• InChiKey: FSFYGQQWENXEBB-UHFFFAOYSA-N

物化性质

• 熔点：
  273 °C
• 沸点：
  545.1±35.0 °C(Predicted)
• 密度：
  1.503±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Nitro-imidazol-4-(N-methyl)-carboxamid 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 以97%的产率得到(9ci)-5-氨基-n-甲基-1H-咪唑-4-羧酰胺
  参考文献：
  名称：

  Antitumor imidazotetrazines. 14. Synthesis and antitumor activity of 6- and 8-substituted imidazo[5,1-d]-1,2,3,5-tetrazinones and 8-substituted pyrazolo[5,1-d]-1,2,3,5-tetrazinones

  摘要：

  The systematic variation of the potent antitumor agent mitozolomide (1) is extended to cover alteration of substituents at positions 6 and 8 and to change the imidazo[5,1-d]-1,2,3,5-tetrazinone (1) skeleton to the isomeric pyrazolo-[5,1-d]-1,2,3,5-tetrazinone (17) skeleton. The series of eight 6-alkyl and 6-aralkyl derivatives of 1 showed optimal antitumor activity when the group was small or linear, but activity diminished as size and branching of this substituent increased. This may reflect altered transport characteristics, or failure of the enlarged derivatives to fit a binding site, or possibly a reduced tendency for the derivatives having bulky groups at position 6 to hydrolytically generate the putatively active triazenes (21). Testing of 14 derivatives of 1 differently substituted at position 8 revealed a complex structure-activity relationship, with good antitumor activity obtained for carbamoyl and sulfamoyl groups bearing small substituents. The 8-methylsulfonyl compound had noteworthy activity, but the 8-cyano, 8-nitro, and 8-phenyl derivatives were devoid of useful antitumor activity in these tests. From the limited number of pyrazolotetrazinones (17) reported here, it is suggested that the same conclusions as regards activity also hold true for this ring system.

  DOI：

  10.1021/jm00385a018
• 作为产物：
  描述：

  1,6-dinitro-5H,10H-diimidazo<1,5-a:1',5'-d>pyrazine-5,10-dione 、 甲胺 以 四氢呋喃 为溶剂， 反应 1.0h， 以56%的产率得到5-Nitro-imidazol-4-(N-methyl)-carboxamid
  参考文献：
  名称：

  Antitumor imidazotetrazines. 14. Synthesis and antitumor activity of 6- and 8-substituted imidazo[5,1-d]-1,2,3,5-tetrazinones and 8-substituted pyrazolo[5,1-d]-1,2,3,5-tetrazinones

  摘要：

  The systematic variation of the potent antitumor agent mitozolomide (1) is extended to cover alteration of substituents at positions 6 and 8 and to change the imidazo[5,1-d]-1,2,3,5-tetrazinone (1) skeleton to the isomeric pyrazolo-[5,1-d]-1,2,3,5-tetrazinone (17) skeleton. The series of eight 6-alkyl and 6-aralkyl derivatives of 1 showed optimal antitumor activity when the group was small or linear, but activity diminished as size and branching of this substituent increased. This may reflect altered transport characteristics, or failure of the enlarged derivatives to fit a binding site, or possibly a reduced tendency for the derivatives having bulky groups at position 6 to hydrolytically generate the putatively active triazenes (21). Testing of 14 derivatives of 1 differently substituted at position 8 revealed a complex structure-activity relationship, with good antitumor activity obtained for carbamoyl and sulfamoyl groups bearing small substituents. The 8-methylsulfonyl compound had noteworthy activity, but the 8-cyano, 8-nitro, and 8-phenyl derivatives were devoid of useful antitumor activity in these tests. From the limited number of pyrazolotetrazinones (17) reported here, it is suggested that the same conclusions as regards activity also hold true for this ring system.

  DOI：

  10.1021/jm00385a018

文献信息

• PUSHKAREVA Z. V.; OFITSEROV V. I.; MOKRUSHIN V. S.; AGLITSKAYA K. V., XIMIYA GETEROTSIKL. SOEDIN. <KGSS-AQ>, 1975, HO 8, 1141-1145
  作者：PUSHKAREVA Z. V.、 OFITSEROV V. I.、 MOKRUSHIN V. S.、 AGLITSKAYA K. V.

  DOI：——

  日期：——
• LUNT E.; NEWTON CH. G.; SMITH CH.; STEVENS G. P.; STEVENS M. F. G.; STRAW+, J. MED. CHEM., 30,(1987) N 2, 357-366
  作者：LUNT E.、 NEWTON CH. G.、 SMITH CH.、 STEVENS G. P.、 STEVENS M. F. G.、 STRAW+

  DOI：——

  日期：——

表征谱图