benzyl 5-diazoimidazole-4-carboxylate | 125927-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: benzyl 5-diazoimidazole-4-carboxylate
• 英文别名: benzyl (5Z)-5-diazoimidazole-4-carboxylate
• CAS: 125927-39-1
• 化学式: C₁₁H₈N₄O₂
• 分子量: 228.21
• InChiKey: AWYQWKVKRAXJOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  53
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯乙基异氰酸酯 、 benzyl 5-diazoimidazole-4-carboxylate 以 乙酸乙酯 为溶剂， 反应 18.0h， 以33.3%的产率得到benzyl 3-(2-chloroethyl)-3H-4-oxoimidazo<5,1-d>-1,2,3,5-tetrazine-8-carboxylate
  参考文献：
  名称：

  Antitumor imidazotetrazines. 20. Preparation of the 8-acid derivative of mitozolomide and its utility in the preparation of active antitumor agents

  摘要：

  The preparation of 3-(2-chlorethyl)-4-oxo-3H-imidazo[5,1-d]-1,2,3,5- tetrazine-8-carboxylic acid, a key derivative of mitozolomide in our exploration of the structure-activity relationships of this class of antitumor agents, is described. The facile conversion to the 8-carbonyl chloride gave a derivative that reacted preferentially with nucleophiles at the 8-position rather than at the reactive 4-oxo group, allowing the preparation of a wide range of ester, thioester, amide (including an amide derived from an amino acid), hydroxamic acid, hydrazide and sulfoximide, azide and diazoacetyl derivatives. The in vivo activity is presented of a range of these compounds against TLX5 lymphoma and L1210 leukemia cell lines.

  DOI：

  10.1021/jm00167a018
• 作为产物：
  描述：

  benzyl 5-nitroimidazole-4-carboxylate 在 platinum(IV) oxide 盐酸 、 氢气 、 sodium nitrite 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 benzyl 5-diazoimidazole-4-carboxylate
  参考文献：
  名称：

  Antitumor imidazotetrazines. 20. Preparation of the 8-acid derivative of mitozolomide and its utility in the preparation of active antitumor agents

  摘要：

  The preparation of 3-(2-chlorethyl)-4-oxo-3H-imidazo[5,1-d]-1,2,3,5- tetrazine-8-carboxylic acid, a key derivative of mitozolomide in our exploration of the structure-activity relationships of this class of antitumor agents, is described. The facile conversion to the 8-carbonyl chloride gave a derivative that reacted preferentially with nucleophiles at the 8-position rather than at the reactive 4-oxo group, allowing the preparation of a wide range of ester, thioester, amide (including an amide derived from an amino acid), hydroxamic acid, hydrazide and sulfoximide, azide and diazoacetyl derivatives. The in vivo activity is presented of a range of these compounds against TLX5 lymphoma and L1210 leukemia cell lines.

  DOI：

  10.1021/jm00167a018

文献信息

• Tetrazines
  申请人：MAY & BAKER LIMITED

  公开号：EP0252682A3

  公开（公告）日：1990-01-10

  Tetrazines of the formula: wherein R¹ represents cycloalkyl, optionally substituted alkyl, alkenyl or alkynyl, A¹ represents nitrogen or -CR³= wherein R³ represents hydrogen or a substituent, A² represents nitrogen or, when A¹ represents nitrogen, A² represents nitrogen or a group -CR³= as hereinbefore defined, Z¹ represents oxygen or sulphur, and R² represents a cyano or azidocarbonyl group or a group of the formula -COZ²R⁹, -CONHOR⁹, -CONHNR⁹R¹⁰, -CONHNHCOOR⁹, -CONHNHCONHR⁹ -COCR¹¹=N₂, -CONHR¹² or -CON=S(O)R¹³R¹⁴ wherein Z² is oxygen or sulphur and R⁹ and R¹⁰ each represents hydrogen, alkyl which may carry an optionally substituted phenyl substituent, or represents optionally substituted phenyl, R¹¹ represents hydrogen or alkyl, and R¹² represents optionally substituted alkyl and R¹³ and R¹⁴ each represent alkyl, and when R¹, R², or R³ represents or contains an acidic group, salts thereof are useful as pharmaceuticals; processes for their preparation and new intermediates are described.

  公式为：其中R¹代表环烷基、可选取代基的烷基、烯基或炔基；A¹代表氮或-CR³=，其中R³代表氢或取代基；A²代表氮或，当A¹代表氮时，A²代表氮或一个如上所定义的-CR³=基团；Z¹代表氧或硫；R²代表氰基或叠氮基，或者代表公式-COZ²R⁹、-CONHOR⁹、-CONHNR⁹R¹⁰、-CONHNHCOOR⁹、-CONHNHCONHR⁹、-COCR¹¹=N₂、-CONHR¹²或-CON=S(O)R¹³R¹⁴中的一种基团，其中Z²代表氧或硫，R⁹和R¹⁰分别代表氢、可携带可选取代苯基的烷基，或代表可选取代苯基；R¹¹代表氢或烷基；R¹²代表可选取代烷基；R¹³和R¹⁴各代表烷基。当R¹、R²或R³代表或含有酸性基团时，其盐可用作药物；描述了其制备过程和新的中间体。
• Antitumor imidazotetrazines. 20. Preparation of the 8-acid derivative of mitozolomide and its utility in the preparation of active antitumor agents
  作者：K. R. Horspool、M. F. G. Stevens、Christopher G. Newton、E. Lunt、R. J. A. Walsh、B. L. Pedgrift、G. U. Baig、F. Lavelle、C. Fizames

  DOI：10.1021/jm00167a018

  日期：1990.5

  The preparation of 3-(2-chlorethyl)-4-oxo-3H-imidazo[5,1-d]-1,2,3,5- tetrazine-8-carboxylic acid, a key derivative of mitozolomide in our exploration of the structure-activity relationships of this class of antitumor agents, is described. The facile conversion to the 8-carbonyl chloride gave a derivative that reacted preferentially with nucleophiles at the 8-position rather than at the reactive 4-oxo group, allowing the preparation of a wide range of ester, thioester, amide (including an amide derived from an amino acid), hydroxamic acid, hydrazide and sulfoximide, azide and diazoacetyl derivatives. The in vivo activity is presented of a range of these compounds against TLX5 lymphoma and L1210 leukemia cell lines.