ethyl N-<6-amino-4-(2-benzylidene-1-methylhydrazino)-nitropyridin-2-yl>carbamate | 123753-72-0

• 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: ethyl N-<6-amino-4-(2-benzylidene-1-methylhydrazino)-nitropyridin-2-yl>carbamate
• 英文别名: ethyl N-[6-amino-4-[(benzylideneamino)-methylamino]-5-nitropyridin-2-yl]carbamate
• CAS: 123753-72-0
• 化学式: C₁₆H₁₈N₆O₄
• 分子量: 358.357
• InChiKey: GJFZQPGGVILGMX-UHFFFAOYSA-N

物化性质

• 熔点：
  191-193 °C (decomp)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  135.98
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl N-<6-amino-4-(2-benzylidene-1-methylhydrazino)-nitropyridin-2-yl>carbamate 在 镍 氢气 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 1.25h， 生成 (5,6-Diamino-4-{N-methyl-N'-[1-phenyl-meth-(Z)-ylidene]-hydrazino}-pyridin-2-yl)-carbamic acid ethyl ester
  参考文献：
  名称：

  Antimitotic agents. Synthesis of imidazo[4,5-c]pyridin-6-ylcarbamates and imidazo[4,5-b]pyridin-5-ylcarbamates

  摘要：

  Cyclization of ethyl 5,6-diamino-4-hydrazinopyridin-2-ylcarbamate (10) with a mixture of CS2 and Et3N in dimethylacetamide gave mainly ethyl 1,4-diamino-2(3H)-thioxoimidazo[4,5-c]pyridin-6-ylcarbamate (15), whereas, in the absence of dimethylacetamide, a double cyclization gave mainly ethyl 5-amino-2(1H)-4-dithioxodiimidazo-[4,5-b:5,4-c]pyridin-7-ylcarb amate (16). Cyclization of the benzylidenehydrazino derivative (6) of 10 with either CS2-Et3N or (EtO)3CH-HCl gave 1-(benzylideneamino)imidazo[4,5-c]pyridines 11 and 7 as major products and 7-(benzylidenehydrazino)imidazo[4,5-b]pyridines 12 and 8 as minor products. Dethiolation of 11 to give 7 and of 12 to give 8 was effected with excess Raney nickel in refluxing ethanol. The benzylidene group of 11 was removed with hydrazine in ethanolic HCl to give 15. This key compound was condensed with benzaldehydes to give 1-benzylideneamino derivatives (20, 21) and alkylated with benzyl halides to give 2-benzylthio derivatives (24-26). In addition, cyclization of ethyl 5,6-diamino-4-(benzylidene-1-methylhydrazino)pyridin-2-ylcarbam ate (30) with (EtO)3CH provided a method for the synthesis of an imidazo[4,5-c]- and -[4,5-b]pyridines gave compounds that inhibited proliferation of growth and caused mitotic arrest against lymphoid leukemia L1210 at micromolar concentrations. However, the more active in vitro compounds (7, 8, 24-26) gave only borderline activity in mice against lymphocytic leukemia P388.

  DOI：

  10.1021/jm00164a030
• 作为产物：
  描述：

  (6-amino-4-chloro-5-nitropyridin-2-yl)carbamate 以 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 16.0h， 生成 ethyl N-<6-amino-4-(2-benzylidene-1-methylhydrazino)-nitropyridin-2-yl>carbamate
  参考文献：
  名称：

  Antimitotic agents. Synthesis of imidazo[4,5-c]pyridin-6-ylcarbamates and imidazo[4,5-b]pyridin-5-ylcarbamates

  摘要：

  Cyclization of ethyl 5,6-diamino-4-hydrazinopyridin-2-ylcarbamate (10) with a mixture of CS2 and Et3N in dimethylacetamide gave mainly ethyl 1,4-diamino-2(3H)-thioxoimidazo[4,5-c]pyridin-6-ylcarbamate (15), whereas, in the absence of dimethylacetamide, a double cyclization gave mainly ethyl 5-amino-2(1H)-4-dithioxodiimidazo-[4,5-b:5,4-c]pyridin-7-ylcarb amate (16). Cyclization of the benzylidenehydrazino derivative (6) of 10 with either CS2-Et3N or (EtO)3CH-HCl gave 1-(benzylideneamino)imidazo[4,5-c]pyridines 11 and 7 as major products and 7-(benzylidenehydrazino)imidazo[4,5-b]pyridines 12 and 8 as minor products. Dethiolation of 11 to give 7 and of 12 to give 8 was effected with excess Raney nickel in refluxing ethanol. The benzylidene group of 11 was removed with hydrazine in ethanolic HCl to give 15. This key compound was condensed with benzaldehydes to give 1-benzylideneamino derivatives (20, 21) and alkylated with benzyl halides to give 2-benzylthio derivatives (24-26). In addition, cyclization of ethyl 5,6-diamino-4-(benzylidene-1-methylhydrazino)pyridin-2-ylcarbam ate (30) with (EtO)3CH provided a method for the synthesis of an imidazo[4,5-c]- and -[4,5-b]pyridines gave compounds that inhibited proliferation of growth and caused mitotic arrest against lymphoid leukemia L1210 at micromolar concentrations. However, the more active in vitro compounds (7, 8, 24-26) gave only borderline activity in mice against lymphocytic leukemia P388.

  DOI：

  10.1021/jm00164a030

文献信息

• Antimitotic agents. Synthesis of imidazo[4,5-c]pyridin-6-ylcarbamates and imidazo[4,5-b]pyridin-5-ylcarbamates
  作者：Carroll Temple

  DOI：10.1021/jm00164a030

  日期：1990.2

  Cyclization of ethyl 5,6-diamino-4-hydrazinopyridin-2-ylcarbamate (10) with a mixture of CS2 and Et3N in dimethylacetamide gave mainly ethyl 1,4-diamino-2(3H)-thioxoimidazo[4,5-c]pyridin-6-ylcarbamate (15), whereas, in the absence of dimethylacetamide, a double cyclization gave mainly ethyl 5-amino-2(1H)-4-dithioxodiimidazo-[4,5-b:5,4-c]pyridin-7-ylcarb amate (16). Cyclization of the benzylidenehydrazino derivative (6) of 10 with either CS2-Et3N or (EtO)3CH-HCl gave 1-(benzylideneamino)imidazo[4,5-c]pyridines 11 and 7 as major products and 7-(benzylidenehydrazino)imidazo[4,5-b]pyridines 12 and 8 as minor products. Dethiolation of 11 to give 7 and of 12 to give 8 was effected with excess Raney nickel in refluxing ethanol. The benzylidene group of 11 was removed with hydrazine in ethanolic HCl to give 15. This key compound was condensed with benzaldehydes to give 1-benzylideneamino derivatives (20, 21) and alkylated with benzyl halides to give 2-benzylthio derivatives (24-26). In addition, cyclization of ethyl 5,6-diamino-4-(benzylidene-1-methylhydrazino)pyridin-2-ylcarbam ate (30) with (EtO)3CH provided a method for the synthesis of an imidazo[4,5-c]- and -[4,5-b]pyridines gave compounds that inhibited proliferation of growth and caused mitotic arrest against lymphoid leukemia L1210 at micromolar concentrations. However, the more active in vitro compounds (7, 8, 24-26) gave only borderline activity in mice against lymphocytic leukemia P388.