3-oxo-3-(2,5,6-trifluoro-4-methoxypyridin-3-yl)propanoic acid ethyl ester | 858860-05-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-oxo-3-(2,5,6-trifluoro-4-methoxypyridin-3-yl)propanoic acid ethyl ester
• 英文别名: ethyl 3-oxo-3-(2,5,6-trifluoro-4-methoxypyridin-3-yl)propanoate
• CAS: 858860-05-6
• 化学式: C₁₁H₁₀F₃NO₄
• 分子量: 277.2
• InChiKey: UECAYGFJRVVPMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-oxo-3-(2,5,6-trifluoro-4-methoxypyridin-3-yl)propanoic acid ethyl ester 在 四氢呋喃 、 sodium hydroxide 、 乙酸酐 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 18.5h， 生成 7-(3-tert-Butoxycarbonylamino-pyrrolidin-1-yl)-6-fluoro-5-methoxy-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and antibacterial activity of 5-methoxy- and 5-hydroxy-6-fluoro-1,8-naphthyridone-3-carboxylic acid derivatives

  摘要：

  A series of 5-methoxy- and 5-hydroxy-6-fluoro-1,8-naphthyridone-3-carboxylic acid derivatives were prepared and evaluated for cell-free bacterial protein synthesis inhibition and whole cell antibacterial activity. When compared to the analogous 5-hydrogen compounds, the presence of the 5-OH group negatively affects biochemical potency. However, a tolerance of the 5-methoxy group is indicated. Only moderate whole cell antibacterial activity is seen, but this could be due to poor cellular penetration, Because only a few 7-position variants were made for this study, further investigation into this novel series combining a broader range of 7-amino derivatives with these 5-position modifications is warranted. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.007
• 作为产物：
  描述：

  3-氯-2,4,5,6-四氟吡啶 在 palladium on activated charcoal 正丁基锂 、 草酰氯 、 氢气 、 三乙胺 、 N,N-二甲基甲酰胺 、 乙腈 、 magnesium chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、303.98 kPa 条件下， 反应 51.5h， 生成 3-oxo-3-(2,5,6-trifluoro-4-methoxypyridin-3-yl)propanoic acid ethyl ester
  参考文献：
  名称：

  Synthesis and antibacterial activity of 5-methoxy- and 5-hydroxy-6-fluoro-1,8-naphthyridone-3-carboxylic acid derivatives

  摘要：

  A series of 5-methoxy- and 5-hydroxy-6-fluoro-1,8-naphthyridone-3-carboxylic acid derivatives were prepared and evaluated for cell-free bacterial protein synthesis inhibition and whole cell antibacterial activity. When compared to the analogous 5-hydrogen compounds, the presence of the 5-OH group negatively affects biochemical potency. However, a tolerance of the 5-methoxy group is indicated. Only moderate whole cell antibacterial activity is seen, but this could be due to poor cellular penetration, Because only a few 7-position variants were made for this study, further investigation into this novel series combining a broader range of 7-amino derivatives with these 5-position modifications is warranted. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.007

文献信息

• NOVEL PYRIDONE CARBOXYLIC ACID DERIVATIVE OR SALT THEREOF
  申请人：WAKUNAGA PHARMACEUTICAL CO., LTD.

  公开号：US20200062752A1

  公开（公告）日：2020-02-27

  It is intended to provide a novel compound having high antitumor activity and low toxicity to normal cells. The present invention provides a pyridone carboxylic acid derivative represented by the following formula (1) or a salt thereof wherein R 1 represents a hydrogen atom, a halogen atom or the like; R 2 represents a hydrogen atom, a halogen atom or the like; R 3 to R 6 each represent a hydrogen atom or the like; R 7 represents a hydrogen atom or the like; R 8 represents a hydrogen atom, a halogen atom, the following formula (a) (wherein R a1 and R a2 each represent a hydrogen atom, a hydroxy group, an optionally substituted lower alkyl group or the like) or the like, or R 7 and R 8 together represent —N—OR 10 (wherein R 10 represents a hydrogen atom, an optionally substituted lower alkyl group, or an aralkyl group), or R 7 and R 8 form an optionally substituted 4- to 6-membered saturated hetero ring together with the adjacent carbon atom, or the like; R 9 represents a hydrogen atom or the like; X represents a nitrogen atom or the like; and Y represents a nitrogen atom or the like.

  本发明旨在提供一种具有高抗肿瘤活性和低毒性对正常细胞的新型化合物。本发明提供一种由以下式(1)表示的吡啶酮羧酸衍生物或其盐，其中R1代表氢原子、卤素原子或类似物；R2代表氢原子、卤素原子或类似物；R3至R6各自代表氢原子或类似物；R7代表氢原子或类似物；R8代表氢原子、卤素原子、以下式(a)（其中Ra1和Ra2各自代表氢原子、羟基、可选择取代的低烷基基团或类似物）或类似物，或者R7和R8一起代表—N—OR10（其中R10代表氢原子、可选择取代的低烷基基团或芳基烷基基团），或者R7和R8与相邻碳原子一起形成可选择取代的4-至6元饱和杂环，或类似物；R9代表氢原子或类似物；X代表氮原子或类似物；Y代表氮原子或类似物。