{6-Amino-4-[2-[(Z)-hydroxyimino]-2-(4-methoxy-phenyl)-ethylamino]-5-nitro-pyridin-2-yl}-carbamic acid ethyl ester | 82585-68-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: {6-Amino-4-[2-[(Z)-hydroxyimino]-2-(4-methoxy-phenyl)-ethylamino]-5-nitro-pyridin-2-yl}-carbamic acid ethyl ester
• 英文别名: ethyl N-[6-amino-4-[[2-hydroxyimino-2-(4-methoxyphenyl)ethyl]amino]-5-nitropyridin-2-yl]carbamate
• CAS: 82585-68-0
• 化学式: C₁₇H₂₀N₆O₆
• 分子量: 404.382
• InChiKey: GIPDESJHCSZBOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  177
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  {6-Amino-4-[2-[(Z)-hydroxyimino]-2-(4-methoxy-phenyl)-ethylamino]-5-nitro-pyridin-2-yl}-carbamic acid ethyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以53%的产率得到{6-Amino-4-[2-(4-methoxy-phenyl)-2-oxo-ethylamino]-5-nitro-pyridin-2-yl}-carbamic acid ethyl ester
  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
• 作为产物：
  描述：

  (6-amino-4-chloro-5-nitropyridin-2-yl)carbamate 、 2-Amino-1-(4-methoxy-phenyl)-ethanone oxime; hydrochloride 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以55%的产率得到{6-Amino-4-[2-[(Z)-hydroxyimino]-2-(4-methoxy-phenyl)-ethylamino]-5-nitro-pyridin-2-yl}-carbamic acid ethyl ester
  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