4-<(4,5-dihydro-2-methylthio)-1-imidazolylcarbonyl>-1-methyl-5-nitropyrazole | 121568-19-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 4-<(4,5-dihydro-2-methylthio)-1-imidazolylcarbonyl>-1-methyl-5-nitropyrazole
• 英文别名: 4-<(4,5-dihydro-2-methylthio-1H-imidazol-1-yl)carbonyl>-1-methyl-5-nitro-1H-pyrazole；(1-Methyl-5-nitropyrazol-4-yl)-(2-methylsulfanyl-4,5-dihydroimidazol-1-yl)methanone
• CAS: 121568-19-2
• 化学式: C₉H₁₁N₅O₃S
• 分子量: 269.284
• InChiKey: GZTJHGQTVUCPPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-<(4,5-dihydro-2-methylthio)-1-imidazolylcarbonyl>-1-methyl-5-nitropyrazole 在 溶剂黄146 、 锌 作用下， 生成 1,6,7,8-tetrahydro-1-methyl-4H-imidazo<1,2-a>pyrazolo<3,4-d>pyrimidin-4-one
  参考文献：
  名称：

  Studies on 1,2,4-Benzothiadiazine 1,1-Dioxides VII and Quinazolinones IV: Synthesis of Novel Built-In Hydroxyguanidine Tricycles as Potential Anticancer Agents

  摘要：

  Two representative built-in hydroxyguanidine tricycles containing 1,2,4-benzothiadiazine 1,1-dioxides (3) and quinazolinones (4) were prepared by reductive cyclization of 1-(2-nitrophenyl-sulfonyl)-2-benzylthio-2-imidazoline (9a), 1-(2-nitrophenylsulfonyl)-2-benzylthio-1,4,5,6-tetrahydropyrimidine (9b), 1-(2-nitrobenzoyl)-2-benzylthio-2-imidazolidine (10a) and 1-(2-nitrobenzoyl)-2-benzyl-thio-1,4,5,6-tetrahydropyrimidine hydrobromide respectively (10b) with zinc dust in acetic acid under ice-cooling. 2,10-Dihydro-10-hydroxy-3H-imidazo[1,2-b][1,2,4]benzothiadiazine 5,5-dioxide (3a) and 2,3,4,11-tetrahydro-11-hydroxypyrimido[1,2-b][1,2,4]benzothiadiazine 6,6-dioxide (3b) were found to be active against solid tumor cell lines such as KB, Colo 205, HeLa, and Hepa-2.

  DOI：

  10.3987/com-92-6285
• 作为产物：
  描述：

  1-甲基-5-硝基吡唑-4-甲酸 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-<(4,5-dihydro-2-methylthio)-1-imidazolylcarbonyl>-1-methyl-5-nitropyrazole
  参考文献：
  名称：

  Peet, Norton P.; Malecha, James; LeTourneau, Michael E., Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 257 - 264

  摘要：

  DOI：

文献信息

• PEET, NORTON P.;MALECHA, JAMES;LETOURNEAU, MICHAEL E.;SUNDER, SHYAM, J. HETEROCYCL. CHEM., 26,(1989) N, C. 257-264
  作者：PEET, NORTON P.、MALECHA, JAMES、LETOURNEAU, MICHAEL E.、SUNDER, SHYAM

  DOI：——

  日期：——
• Peet, Norton P.; Malecha, James; LeTourneau, Michael E., Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 257 - 264
  作者：Peet, Norton P.、Malecha, James、LeTourneau, Michael E.、Sunder, Shyam

  DOI：——

  日期：——
• Studies on 1,2,4-Benzothiadiazine 1,1-Dioxides VII and Quinazolinones IV: Synthesis of Novel Built-In Hydroxyguanidine Tricycles as Potential Anticancer Agents
  作者：Ji-Wang Chern、Yen-Chywan Liaw、Chien-Shu Chen、Jiann-Gwo Rong、Chien-Lin Huang、Chao-Han Chan、Andrew H.-J. Wang

  DOI：10.3987/com-92-6285

  日期：——

  Two representative built-in hydroxyguanidine tricycles containing 1,2,4-benzothiadiazine 1,1-dioxides (3) and quinazolinones (4) were prepared by reductive cyclization of 1-(2-nitrophenyl-sulfonyl)-2-benzylthio-2-imidazoline (9a), 1-(2-nitrophenylsulfonyl)-2-benzylthio-1,4,5,6-tetrahydropyrimidine (9b), 1-(2-nitrobenzoyl)-2-benzylthio-2-imidazolidine (10a) and 1-(2-nitrobenzoyl)-2-benzyl-thio-1,4,5,6-tetrahydropyrimidine hydrobromide respectively (10b) with zinc dust in acetic acid under ice-cooling. 2,10-Dihydro-10-hydroxy-3H-imidazo[1,2-b][1,2,4]benzothiadiazine 5,5-dioxide (3a) and 2,3,4,11-tetrahydro-11-hydroxypyrimido[1,2-b][1,2,4]benzothiadiazine 6,6-dioxide (3b) were found to be active against solid tumor cell lines such as KB, Colo 205, HeLa, and Hepa-2.