4-亚硝基-5-苯基-1H-咪唑 | 106232-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-亚硝基-5-苯基-1H-咪唑
• 英文名称: 4(5)-nitroso-5(4)-phenylimidazole
• 英文别名: 4-Nitroso-5-phenylimidazole；4-nitroso-5-phenyl-1H-imidazole
• CAS: 106232-36-4
• 化学式: C₉H₇N₃O
• 分子量: 173.174
• InChiKey: LFIVWAMAAWKOGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-亚硝基-5-苯基-1H-咪唑 在 乙醇 、 羟胺 作用下， 生成 3-formylamino-4-phenylfurazan
  参考文献：
  名称：

  Cusmano; Ruccia, Gazzetta Chimica Italiana, 1958, vol. 88, p. 463,480

  摘要：

  DOI：
• 作为产物：
  描述：

  4-苯基咪唑 在 sodium ethanolate 、 亚硝酸异戊酯 作用下， 以 乙醇 为溶剂， 反应 144.0h， 生成 4-亚硝基-5-苯基-1H-咪唑
  参考文献：
  名称：

  Acid-catalyzed decomposition of 4(5)-nitroso-5(4)-phenylimidazole in methanol and water

  摘要：

  DOI：

  10.1021/jo00383a040

文献信息

• Nitrosoimidazoles: highly bactericidal analogs of 5-nitroimidazole drugs
  作者：William J. Ehlhardt、Bernard B. Beaulieu、Peter Goldman

  DOI：10.1021/jm00397a009

  日期：1988.2

  relative biological activity of 4- and 5-nitroimidazoles examined previously. In contrast, all three nitroso compounds are considerably more bactericidal than their analogous nitro compounds under both aerobic and anaerobic conditions, a finding that provides direct evidence that reduction of the nitro group is responsible for activation of the nitroimidazoles. Further evidence is also consistent with

  据信甲硝唑和相关的5-硝基咪唑通过硝基的还原而被活化，并且活性物质具有中等氧化态的氮官能度。然而，已证明难以治疗性地制备和分离5-硝基咪唑的活性形式。为了解决这个问题，我们从4（5）-nitroso-5（4）-制备了1-methyl-4-phenyl-5-nitrosoimidazole（3）和1-methyl-4-nitroso-5-phenylimidazole（5）-苯基咪唑（1）。我们还制备了同源的硝基咪唑。发现DNA修复缺陷的大肠杆菌突变体对1-甲基-4-苯基-5-硝基咪唑（4）和甲硝唑均敏感，但对1-甲基-4-硝基-5-苯基咪唑（6）具有相当的抵抗力。 ，与先前研究的4-和5-硝基咪唑的相对生物学活性相符的发现。相反，在需氧和厌氧条件下，所有三种亚硝基化合物均比其类似的硝基化合物具有更大的杀菌作用，这一发现提供了直接的证据，即硝基的还原是硝基咪唑活化的原因。尽管更保守的解释是简
• 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
  作者：Edward Lunt、Christopher G. Newton、Christopher Smith、Graham P. Stevens、Malcolm F. G. Stevens、Colin G. Straw、Roger J. A. Walsh、Peter J. Warren、Christian Fizames

  DOI：10.1021/jm00385a018

  日期：1987.2

  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.
• Cusmano; Didonna, Gazzetta Chimica Italiana, 1955, vol. 85, p. 208,215
  作者：Cusmano、Didonna

  DOI：——

  日期：——
• Ruccia,M.; Natale,G., Gazzetta Chimica Italiana, 1960, vol. 90, p. 1047 - 1055
  作者：Ruccia,M.、Natale,G.

  DOI：——

  日期：——
• Radical anions of nitrosoimidazoles: Putative intermediates in the mechanism of action of nitroimidazole antibiotics
  作者：Martyn C.R. Symons、W. Russell Bowman、Peter F. Taylor

  DOI：10.1016/s0040-4039(00)94737-3

  日期：1990.1

表征谱图