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。