6,6,16-氟十三六烷酸 | 90521-92-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 6,6,16-氟十三六烷酸
• 英文名称: 5-Amino-2-isopropyl-1H-imidazole-4-carboxylic acid amide; hydrochloride
• 英文别名: 4-amino-2-propan-2-yl-1H-imidazole-5-carboxamide;hydrochloride
• CAS: 90521-92-9
• 化学式: C₇H₁₂N₄O*ClH
• 分子量: 204.659
• InChiKey: DNVIOYVCIFCGRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.64
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  97.8
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,6,16-氟十三六烷酸 在 溶剂黄146 、 sodium nitrite 作用下， 以 乙酸乙酯 为溶剂， 反应 120.0h， 生成 3-(2-Chloro-ethyl)-6-isopropyl-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid amide
  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：

  Thioisobutyrimidic acid benzyl ester; hydrochloride 、 2-氨基-2-氰基乙酰胺 以 乙醇 为溶剂， 反应 0.25h， 以42.5%的产率得到6,6,16-氟十三六烷酸
  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

• 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：——