4-diazo-4H-imidazol-5-carbonitril | 53000-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-diazo-4H-imidazol-5-carbonitril
• 英文别名: 4-diazo-4H-imidazole-5-carbonitrile；5-diazo-5H-imidazole-4-carbonitrile；(5Z)-5-diazoimidazole-4-carbonitrile
• CAS: 53000-41-2
• 化学式: C₄HN₅
• 分子量: 119.085
• InChiKey: PDSXUDBYKBJDTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-diazo-4H-imidazol-5-carbonitril 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以46%的产率得到5(4)-azidoimidazole-4(5)-carbonitrile
  参考文献：
  名称：

  Synthesis and properties of analogs of 5(or 4)-aminoimidazole-4(or 5)-carboxamide (aica) and purines. 12. Investigation of the interaction of 4-chloroimidazo[4,5-d]-1,2,3-triazine with nucleophiles

  摘要：

  DOI：

  10.1007/bf00515366
• 作为产物：
  描述：

  5-氨基-1H-咪唑-4-甲腈盐酸盐 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.75h， 生成 4-diazo-4H-imidazol-5-carbonitril
  参考文献：
  名称：

  Andersen, Knud Erik; Pedersen, Erik B., Liebigs Annalen der Chemie, 1986, # 6, p. 1012 - 1020

  摘要：

  DOI：

文献信息

• Antitumor Imidazotetrazines. 35. New Synthetic Routes to the Antitumor Drug Temozolomide
  作者：Yongfeng Wang、Malcolm F. G. Stevens、Tze-ming Chan、Donald DiBenedetto、Zhe-xing Ding、Dinesh Gala、Donald Hou、Max Kugelman、William Leong、Shen-chun Kuo、Janet L. Mas、Doris P. Schumacher、Bruce P. Shutts、Lyman Smith、Zheng-Yun J. Zhan、William T. Thomson

  DOI：10.1021/jo970802l

  日期：1997.10.1

  Three new pathways to the antitumor drug temozolomide (4) have been explored via intermediates 3, 6, and 7. The key intermediate 5-amino-1-(N-methylcarbamoyl)imidazole-4-carboxamide (6) has been successfully converted to 4 in 45% yield by employing sodium nitrite in aqueous tartaric acid at 0-5 degrees C, Compound 6 is prepared from nitrophenyl carbamate 14a and methylamine or directly from 5-aminoimidazole-4-carboxamide (13) and either methyl isocyanate or N-methylcarbamoyl chloride. Temozolomide (4) is also prepared from 8-cyano-3-methylimidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one (7) by hydrolysis to the hydrochloride salt of 4 in 10 M hydrochloric acid. Compound 7 is prepared from either 5-diazoimidazole-4-carbonitrile (28) and methyl isocyanate or by diazotization of 5-amino-1-(N-methylcarbamoyl)imidazole-4-carbonitrile (25). Attempts to cyclize 5-(3-methyltriazen-1-yl)imidazole-4-carboxamide (3) with phosgene or phosgene equivalents were unsuccessful: only 2-azahypoxanthine (11) was isolated.
• 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.
• Synthesis and properties of analogs of 5(4)-aminoimidazole-4(5)-carboxamide and purines. 15. Ring opening in imidazo[4,5-d]-1,2,3-triazines
  作者：V. K. Usova、I. S. Selezneva、T. A. Pospelova、V. S. Mokrushin

  DOI：10.1007/bf00487307

  日期：1989.9
• Baig, Ghouse Unissa; Stevens, Malcolm F. G.; Stone, Robert, Journal of the Chemical Society. Perkin transactions I, 1982, # 8, p. 1811 - 1820
  作者：Baig, Ghouse Unissa、Stevens, Malcolm F. G.、Stone, Robert

  DOI：——

  日期：——
• Synthesis of 6,8-substituted derivatives of imidazo[5,1-c][1,2,4]triazines and 1,4-dihydroimidazo[5,1-c][1,2,4]triazin-4-ones
  作者：M. A. Bezmaternykh、V. S. Mokrushin、T. A. Pospelova、O. S. El'tsov

  DOI：10.1007/bf02252280

  日期：1998.6