[6-Amino-5-nitro-4-(2-oxo-2-phenyl-ethylamino)-pyridin-2-yl]-carbamic acid ethyl ester | 82585-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [6-Amino-5-nitro-4-(2-oxo-2-phenyl-ethylamino)-pyridin-2-yl]-carbamic acid ethyl ester
• 英文别名: ethyl N-[6-amino-5-nitro-4-(phenacylamino)pyridin-2-yl]carbamate
• CAS: 82585-75-9
• 化学式: C₁₆H₁₇N₅O₅
• 分子量: 359.341
• InChiKey: YCVCBVPDZROICR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  152
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [6-Amino-5-nitro-4-(2-oxo-2-phenyl-ethylamino)-pyridin-2-yl]-carbamic acid ethyl ester 在 镍 氢气 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 6.0h， 以89%的产率得到N-(5-氨基-3-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
• 作为产物：
  描述：

  (6-amino-4-chloro-5-nitropyridin-2-yl)carbamate 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 10.0h， 生成 [6-Amino-5-nitro-4-(2-oxo-2-phenyl-ethylamino)-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

• Novel 1,2-dihydropyrido(3,4-b)-pyrazines and method for preparing same
  申请人：Southern Research Institute

  公开号：EP0061178A2

  公开（公告）日：1982-09-29

  1,2-pihydropyrido[3,4-b]pyrazines are provided which possess antifungal and anticancer activity. The compounds have the structure: wherein x has a value of 1, 2 or 3; R1 is a lower alkyl group, R2 has the meaning as defined in the description and R3 and R4 are either both hydrogen or one is hydrogen and the other is a lower alkyl group. Processes and intermediates for the preparation of compounds of formula I are disclosed as well as pharmaceutical compositions containing compounds of formula I.

  本研究提供了具有抗真菌和抗癌活性的 1,2-二氢吡啶并[3,4-b]吡嗪类化合物。这些化合物具有如下结构 其中 x 的值为 1、2 或 3；R1 为低级烷基，R2 的含义如描述中所定义，R3 和 R4 要么都是氢，要么一个是氢，另一个是低级烷基。 本发明公开了制备式 I 化合物的工艺和中间体，以及含有式 I 化合物的药物组合物。
• Novel intermediates in a process for making novel 1,2-dihydropyrido(3,4-b)-pyrazines
  申请人：Southern Research Institute

  公开号：EP0151765A2

  公开（公告）日：1985-08-21

  The invention relates to compounds of the general formulae in which R1, R2, R3, R4 and x have the meaning defined in the specification. These compounds are valuable novel intermediates for the preparation of novel 1,2-dihydropyrido[3,4-b]-pyrazines.

  本发明涉及通式如下的化合物 其中 R1、R2、R3、R4 和 x 具有说明书中定义的含义。这些化合物是制备新型 1,2-二氢吡啶并[3,4-b]-吡嗪的重要新型中间体。
• 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：——
• TEMPLE, C. G. ,, JR.;MONTGOMERY, J. A.;ELLIOTT, R. D.;WHEELER, G. P.
  作者：TEMPLE, C. G. ,, JR.、MONTGOMERY, J. A.、ELLIOTT, R. D.、WHEELER, G. P.

  DOI：——

  日期：——
• US4450160A
  申请人：——

  公开号：US4450160A

  公开（公告）日：1984-05-22