(5-氨基-3-(4-氨基苯基)-1,2-二氢吡啶并[3,4-b]吡嗪-7-基)-氨基甲酸乙酯 | 82586-02-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (5-氨基-3-(4-氨基苯基)-1,2-二氢吡啶并[3,4-b]吡嗪-7-基)-氨基甲酸乙酯
• 英文名称: [5-Amino-3-(4-amino-phenyl)-1,2-dihydro-pyrido[3,4-b]pyrazin-7-yl]-carbamic acid ethyl ester
• 英文别名: Carbamic acid, (5-amino-3-(4-aminophenyl)-1,2-dihydropyrido(3,4-b)pyrazin-7-yl)-, ethyl ester；ethyl N-[5-amino-3-(4-aminophenyl)-1,2-dihydropyrido[3,4-b]pyrazin-7-yl]carbamate
• CAS: 82586-02-5
• 化学式: C₁₆H₁₈N₆O₂
• 分子量: 326.358
• InChiKey: OYHTZOLNNSQJLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5-氨基-3-(4-氨基苯基)-1,2-二氢吡啶并[3,4-b]吡嗪-7-基)-氨基甲酸乙酯 、 乙醇 生成 ethanol;ethyl N-[5-amino-3-(4-aminophenyl)-1,2-dihydropyrido[3,4-b]pyrazin-7-yl]carbamate
  参考文献：
  名称：

  TEMPLE, C. G. ,, JR.;MONTGOMERY;ELLIOTT, R. D.;WHEELER, G. P.

  摘要：

  DOI：
• 作为产物：
  描述：

  (6-amino-4-chloro-5-nitropyridin-2-yl)carbamate 在 镍 盐酸 、 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 60.0~75.0 ℃ 、101.33 kPa 条件下， 反应 32.0h， 生成 (5-氨基-3-(4-氨基苯基)-1,2-二氢吡啶并[3,4-b]吡嗪-7-基)-氨基甲酸乙酯
  参考文献：
  名称：

  New anticancer agents: synthesis of 1,2-dihydropyrido[3,4-b]pyrazines (1-deaza-7,8-dihydropteridines)

  摘要：

  Reaction of alpha-aminoacetophenone oximes (2) with ethyl 6-amino-4-chloro-5-nitropyridine-2-carbamate (1) gave ethyl 6-amino-5-nitro-4-[(2-oxo-2-phenylethyl)amino]pyridine-2-carbamate oximes (3), which were hydrolyzed under acidic conditions to give the corresponding ketones (4). Related pyridines substituted with a keto side chain were prepared from 1 and 1,3-diaminopropanone oximes and by oxidation of the side-chain hydroxy group of ethyl 6-amino-4- [[3-(N-methyl-N-phenylamino)-2-hydroxypropyl]amino]-5-nitropyridine-7- carbamates (6). Catalytic hydrogenation of the nitro group of 4 over Raney nickel in a large volume of ethanol gave the 1-deaza-7,8-dihydropteridines (7). Several of the oximes 3 were successfully hydrogenated to give 7 directly. The resulting 1-deaza-7,8-dihydropteridines showed potent cytotoxicity against cultured L1210 cells and significant anticancer activity against lymphocytic leukemia P-388 in mice. These biological activities are attributed to the accumulation of cells at mitosis.

  DOI：

  10.1021/jm00351a008

文献信息

• TEMPLE, C. G. ,, JR.;MONTGOMERY;ELLIOTT, R. D.;WHEELER, G. P.
  作者：TEMPLE, C. G. ,, JR.、MONTGOMERY、ELLIOTT, R. D.、WHEELER, G. P.

  DOI：——

  日期：——
• New anticancer agents: synthesis of 1,2-dihydropyrido[3,4-b]pyrazines (1-deaza-7,8-dihydropteridines)
  作者：Carroll Temple、Glynn P. Wheeler、Robert D. Elliott、Jerry D. Rose、Conrad L. Kussner、Robert N. Comber、John A. Montgomery

  DOI：10.1021/jm00351a008

  日期：1982.9

  Reaction of alpha-aminoacetophenone oximes (2) with ethyl 6-amino-4-chloro-5-nitropyridine-2-carbamate (1) gave ethyl 6-amino-5-nitro-4-[(2-oxo-2-phenylethyl)amino]pyridine-2-carbamate oximes (3), which were hydrolyzed under acidic conditions to give the corresponding ketones (4). Related pyridines substituted with a keto side chain were prepared from 1 and 1,3-diaminopropanone oximes and by oxidation of the side-chain hydroxy group of ethyl 6-amino-4- [[3-(N-methyl-N-phenylamino)-2-hydroxypropyl]amino]-5-nitropyridine-7- carbamates (6). Catalytic hydrogenation of the nitro group of 4 over Raney nickel in a large volume of ethanol gave the 1-deaza-7,8-dihydropteridines (7). Several of the oximes 3 were successfully hydrogenated to give 7 directly. The resulting 1-deaza-7,8-dihydropteridines showed potent cytotoxicity against cultured L1210 cells and significant anticancer activity against lymphocytic leukemia P-388 in mice. These biological activities are attributed to the accumulation of cells at mitosis.