{6-Amino-4-[2-[(Z)-hydroxyimino]-2-(4-trifluoromethyl-phenyl)-ethylamino]-5-nitro-pyridin-2-yl}-carbamic acid ethyl ester | 82585-71-5

• 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-[(Z)-hydroxyimino]-2-(4-trifluoromethyl-phenyl)-ethylamino]-5-nitro-pyridin-2-yl}-carbamic acid ethyl ester
• 英文别名: Ethyl [6-amino-4-({2-(hydroxyimino)-2-[4-(trifluoromethyl)phenyl]ethyl}amino)-5-nitropyridin-2-yl]carbamate；ethyl N-[6-amino-4-[[2-hydroxyimino-2-[4-(trifluoromethyl)phenyl]ethyl]amino]-5-nitropyridin-2-yl]carbamate
• CAS: 82585-71-5
• 化学式: C₁₇H₁₇F₃N₆O₅
• 分子量: 442.354
• InChiKey: YIVVRTMODHSFFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  168
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  {6-Amino-4-[2-[(Z)-hydroxyimino]-2-(4-trifluoromethyl-phenyl)-ethylamino]-5-nitro-pyridin-2-yl}-carbamic acid ethyl ester 在 镍 盐酸 、 氢气 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 50.0h， 生成 (5-氨基-1,2-二氢-3-(4-(三氟甲基)苯基)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
• 作为产物：
  描述：

  2-[2-[(E)-Hydroxyimino]-2-(4-trifluoromethyl-phenyl)-ethyl]-isoindole-1,3-dione 在 三乙胺 、 肼 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 {6-Amino-4-[2-[(Z)-hydroxyimino]-2-(4-trifluoromethyl-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

文献信息

• 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.