ethyl 6-amino-4-<<2-hydroxy-3-(N-methyl-N-phenylamino)propyl>amino>-5-nitro-2-pyridinecarbamate | 82585-86-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: ethyl 6-amino-4-<<2-hydroxy-3-(N-methyl-N-phenylamino)propyl>amino>-5-nitro-2-pyridinecarbamate
• 英文别名: ethyl 6-amino-4-{[2-hydroxy-3-(N-methyl-N-phenylamino)propyl]amino}-5-nitro-2-pyridinecarbamate；2-Pyridinecarbamic acid, 6-amino-4-[[2-hydroxy-3-(methylphenylamino)propyl]amino]-5-nitro-, ethyl ester；ethyl N-[6-amino-4-[[2-hydroxy-3-(N-methylanilino)propyl]amino]-5-nitropyridin-2-yl]carbamate
• CAS: 82585-86-2
• 化学式: C₁₈H₂₄N₆O₅
• 分子量: 404.426
• InChiKey: FBNXSOAJCFNWFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  159
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 6-amino-4-<<2-hydroxy-3-(N-methyl-N-phenylamino)propyl>amino>-5-nitro-2-pyridinecarbamate 在 镍 磷酸 、 氢气 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 44.5h， 生成 ethyl 5-amino-1,2-dihydro-3-<(N-methyl-N-phenylamino)methyl>pyrido<3,4-b>pyrazine-7-carbamate
  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：

  N-甲基-N-(环氧乙烷-2-基甲基)苯胺 在 氨 、 三乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 21.0h， 生成 ethyl 6-amino-4-<<2-hydroxy-3-(N-methyl-N-phenylamino)propyl>amino>-5-nitro-2-pyridinecarbamate
  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
  申请人：Southern Research Institute

  公开号：EP0090681A2

  公开（公告）日：1983-10-05

  1,2-Dihydropyrido[3,4-b]pyrazines are provided which possess anticancer activity. The compounds have the structure: wherein x has a value of 1, 2 or 3; Y is CH2 or N(CH3); R1is a lower alkyl group; e.g., an alkyl group containing up to six carbon atoms such as methyl, ethyl, propyl, butyl, etc.; R2 is a member selected from the group consisting of hydrogen, alkyl radicals having from about one to about 12 carbon atoms, preferably from about one to about 6 carbon atoms; alkenyl radicals having from about two to about 15 carbon atoms, preferably from about two to about 10 carbon atoms; cycloalkyl radi- cads having from about three to about 20 carbon atoms, preferably from about three to about 15 carbon atoms; aralkyl and alkaryl radicals having from about six to about 20 carbon atoms, preferably from about six to about 15 carbon atoms; a halogen radical, e.g., chlorine, fluorine, bromine and iodine; a hydroxyl group; an amino group; an alkoxy or aryloxy group; an alkylthio group or an arylthio group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; a sulfonic acid group or alkyl- or arylsulfonyl group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; an alkyl- or arylsulfinyl group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; an alkyl- or aryl mono- or diamino group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; a hydrocarbyl group, such as defined above, carrying halogen, hydroxyl; amino, alkoxy or aryloxy; and, when taken together with the aromatic ring to which it is attached , a fused ring structure such as naphthyl; and R3 and R4 are either both hydrogen or one is hydrogen and the other is a lower alkyl group; provided that when each of R2, R3 and R4 are hydrogen, Y is CH2.

  本研究提供了具有抗癌活性的 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；Y 为 CH2 或 N(CH3)；R1 为低级烷基；例如R1 是低级烷基；例如，含有多达六个碳原子的烷基，如甲基、乙基、丙基、丁基等； R2 是选自下列化合物的成员R2 是选自以下组别的成员：氢、具有约 1 至约 12 个碳原子，最好是约 1 至约 6 个碳原子的烷基；具有约 2 至约 15 个碳原子，最好是约 2 至约 10 个碳原子的烯基；具有约 3 至约 20 个碳原子，最好是约 3 至约 15 个碳原子的环烷基；具有约 6 至约 20 个碳原子，最好是约 6 至约 15 个碳原子的芳烷基和烷芳基；卤素基，例如：氯、氟、溴、烷基、烯烷基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、炔烃基、羟基；氨基；烷氧基或芳氧基；烷硫基或芳硫基，具有约 1 至约 20 个碳原子，最好是约 1 至约 15 个碳原子；磺酸基或烷基或芳基磺酰基，具有约 1 至约 20 个碳原子，最好是约 1 至约 15 个碳原子；烷基或芳基亚磺酰基，具有约 1 至约 20 个碳原子，最好是约 1 至约 15 个碳原子；具有约 1 至约 20 个碳原子，最好是约 1 至约 15 个碳原子的烷基或芳基一元或二元基团； 如上定义的烃基，带有卤素、羟基、氨基、烷氧基或芳氧基；当与所连接的芳环一起时，为融合环结构，如萘基；以及 R3 和 R4 要么都是氢，要么一个是氢，另一个是低级烷基；条件是当 R2、R3 和 R4 都是氢时，Y 为 CH2。
• INHIBITORS OF FTSZ AND USES THEREOF
  申请人：White E. Lucile

  公开号：US20100113429A1

  公开（公告）日：2010-05-06

  The invention relates to inhibitors of FtsZ polymerization and uses thereof.
• US4600716A
  申请人：——

  公开号：US4600716A

  公开（公告）日：1986-07-15
• US4645840A
  申请人：——

  公开号：US4645840A

  公开（公告）日：1987-02-24
• US7718651B2
  申请人：——

  公开号：US7718651B2

  公开（公告）日：2010-05-18

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