(6-Amino-4-{2-(3,4-dichloro-phenyl)-2-[(Z)-hydroxyimino]-ethylamino}-5-nitro-pyridin-2-yl)-carbamic acid ethyl ester | 82585-66-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (6-Amino-4-{2-(3,4-dichloro-phenyl)-2-[(Z)-hydroxyimino]-ethylamino}-5-nitro-pyridin-2-yl)-carbamic acid ethyl ester
• CAS: 82585-66-8
• 化学式: C₁₆H₁₆Cl₂N₆O₅
• 分子量: 443.246
• InChiKey: FNDJLCCRPXHXSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  165.0
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (6-Amino-4-{2-(3,4-dichloro-phenyl)-2-[(Z)-hydroxyimino]-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 6.0h， 以69%的产率得到{6-Amino-4-[2-(3,4-dichloro-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：

  2-{2-(3,4-Dichloro-phenyl)-2-[(E)-hydroxyimino]-ethyl}-isoindole-1,3-dione 在 三乙胺 、 肼 作用下， 以 乙醇 为溶剂， 反应 23.5h， 生成 (6-Amino-4-{2-(3,4-dichloro-phenyl)-2-[(Z)-hydroxyimino]-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