ethyl 4-(1-acetyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2,5-difluoro-β-oxobenzenepropionate | 122858-46-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-(1-acetyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2,5-difluoro-β-oxobenzenepropionate
• 英文别名: ethyl 4-(1-acetyl-1,2,3,6-tetrahydro-4-pyridyl)-2,5-difluoro-β-oxobenzenepropionate；Ethyl 4-(1-acetyl-1,2,3,6-tetrahydro-4-pyridyl)-2,5-difluoro-beta-oxobenzenepropionate；ethyl 3-[4-(1-acetyl-3,6-dihydro-2H-pyridin-4-yl)-2,5-difluorophenyl]-3-oxopropanoate
• CAS: 122858-46-2
• 化学式: C₁₈H₁₉F₂NO₄
• 分子量: 351.35
• InChiKey: GWACMQOKAQHZJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4-(1-acetyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2,5-difluoro-β-oxobenzenepropionate 以 乙酸酐 为溶剂， 生成 ethyl 4-(1-acetyl-1,2,3,6-tetrahydro-pyridin-4-yl)-α-(ethoxymethylene)-2,5-difluoro-β-oxobenzenepropionate
  参考文献：
  名称：

  Antibacterial agents

  摘要：

  描述了一系列新型的喹啉酸、萘啉酸和苯并噁嗪酸，它们作为抗菌剂具有用途。还描述了制备这些化合物的新方法以及新的中间体，以及它们的配方方法和在治疗细菌感染中的应用方法。

  公开号：

  US05081254A1
• 作为产物：
  描述：

  1,4-二溴-2,5-二氟苯 在 盐酸 、 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 63.25h， 生成 ethyl 4-(1-acetyl-1,2,3,6-tetrahydro-pyridin-4-yl)-2,5-difluoro-β-oxobenzenepropionate
  参考文献：
  名称：

  Quinolone antibacterials: synthesis and biological activity of carbon isosteres of the 1-piperazinyl and 3-amino-1-pyrrolidinyl side chains

  摘要：

  A series of 6-fluoro-1,4-dihydro-4-oxo-3-quinoline- and 1,8-naphthyridinecarboxylic acids, substituted at the 7-position with carbon-linked side chains, was synthesized and evaluated for antibacterial activity and DNA-gyrase inhibition. Structural modifications focused on replacement of the heterocyclic nitrogen of the frequently found 1-piperazinyl and 3-amino-1-pyrrolidinyl side chains by an sp2- or an sp3-hybridized carbon. All new compounds displayed high in vitro and in vivo antibacterial activity. Potency relative to the standard nitrogenated agents was dependent on ring size and hybridization of the linking carbon atom of the side chain. Compounds with a 1,2,3,6-tetrahydro-4-pyridinyl substituent at C-7 were equipotent with their 1-piperazinyl analogs, whereas those having a 4-piperidinyl or a 3-amino-1-cyclopentenyl ring at C-7 were less active than the 1-piperazinyl or 3-amino-1-pyrrolidinyl substituted agents, respectively. This relative difference in antibacterial potency did not correlate with the observed activity against gyrase, where the majority of the new compounds were equally or more potent than their nitrogenated counterparts.

  DOI：

  10.1021/jm00066a005

文献信息

• 4-Quinolone-3-carboxylic-acid derivatives and their use as antibacterial agents
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0306764A2

  公开（公告）日：1989-03-15

  A novel series of quinoline-, naphthyridine- and benzoxazine-carboxylic acids (I) useful as antibacterial agents is described. Novel methods for preparing the compounds as well as novel intermediates are also described as are methods for their formulation and the use thereof in treating bacterial infections. where Z is wherein one endocyclic double bond may be present between any two consecutive ring positions or two alternating or nonalternating endocyclic double bonds may be present in the ring; wherein n, n′, n‴, and n˝˝ are each independently 0, 1, or 2; n˝ is 0, 1, 2, or 3; y is 0 or 1; x is 0 or 1; A and B are each independently CH, CH₂, NR₇ wherein R₇ is hydrogen or R₇ is R₈CO wherein R₈ is alkyl of from one to ten carbon atoms, arylalkyl, aryl wherein the aryl or alkyl may be substituted by hydroxy, halogen, COOH, or CONHR₉ wherein R₉ is hydrogen or alkyl of from one to four carbon atoms and when A is NR₇, B can be O or S or when B is NR₇, A can be absent; (CR₁₃R₁₄)n‴ wherein R₁₃ and R₁₄ are each independently hydrogen or lower alkyl; and E is hydrogen, alkyl, OR₁₀ wherein R₁₀ is hydrogen or alkyl, NR₁₁R₁₂ wherein R₁₁ and R₁₂ are each independently hydrogen, lower alkyl, cycloalkyl alkylaryl, alkylheteroaryl, alkanoyl, amidine, peptide urethane, or R₁₁ and R₁₂ when taken together with the nitrogen to which they are attached form a ring of from three to six carbon atoms or

  本文介绍了一系列新型喹啉、萘啶和苯并噁嗪羧酸（I），可用作抗菌剂。此外，还介绍了制备这些化合物以及新型中间体的新方法，以及这些化合物的配制方法和用于治疗细菌感染的方法。 其中 Z 是 其中一个内环双键可存在于任意两个连续的环位置之间，或两个交替或非交替的内环双键可存在于环中； 其中 n、n′、n‴ 和 n˝˝ 各自独立地为 0、1 或 2； n˝ 为 0、1、2 或 3； y 是 0 或 1； x 为 0 或 1； A 和 B 各自独立地为 CH、CH₂、NR₇（其中 R₇ 为氢或 R₇ 为 R₈CO（其中 R₈ 为一至十个碳原子的烷基）、芳烷基、芳基（其中芳基或烷基可被羟基取代）、卤素、COOH 或 CONHR₉，其中 R𠢙 是氢或一至四个碳原子的烷基，当 A 是 NR₇ 时，B 可以是 O 或 S，或者当 B 是 NR₇ 时，A 可以不存在； (CR₁₃R₁₄)n‴ 其中 R₁₃ 和 R₁₄ 各自独立地为氢或低级烷基；以及 E 是氢、烷基、OR₁₀(其中 R₁₀ 是氢或烷基)、NR₁₁R₁₂(其中 R₁₁ 和 R₁₂ 各自独立地是氢、低级烷基、环烷基烷芳基、R₁₁和 R₁₂各自独立地为氢、低级烷基、环烷基烷基芳基、烷基杂芳基、烷酰基、脒、肽聚氨酯，或 R₁₁和 R₁₂与它们所连接的氮一起形成三至六个碳原子的环，或
• US4929613A
  申请人：——

  公开号：US4929613A

  公开（公告）日：1990-05-29
• US5081254A
  申请人：——

  公开号：US5081254A

  公开（公告）日：1992-01-14
• Antibacterial agents
  申请人：Warner-Lambert Company

  公开号：US04929613A1

  公开（公告）日：1990-05-29

  The novel series of quinoline-, naphthyridine- and benzoxazine-carboxylic acids useful as antibacterial agents is described. Novel methods for preparing the compounds as well as novel intermediates are also described as are methods for their formulation and the use thereof in treating bacterial infections.

  描述了喹啉基，萘啉基和苯并噁嗪基羧酸的小说系列，这些化合物可用作抗菌剂。还描述了制备这些化合物的新方法以及新的中间体，以及它们的配方方法以及在治疗细菌感染中的应用方法。
• Quinolone antibacterials: synthesis and biological activity of carbon isosteres of the 1-piperazinyl and 3-amino-1-pyrrolidinyl side chains
  作者：Edgardo Laborde、John S. Kiely、Townley P. Culbertson、Lawrence E. Lesheski

  DOI：10.1021/jm00066a005

  日期：1993.7

  A series of 6-fluoro-1,4-dihydro-4-oxo-3-quinoline- and 1,8-naphthyridinecarboxylic acids, substituted at the 7-position with carbon-linked side chains, was synthesized and evaluated for antibacterial activity and DNA-gyrase inhibition. Structural modifications focused on replacement of the heterocyclic nitrogen of the frequently found 1-piperazinyl and 3-amino-1-pyrrolidinyl side chains by an sp2- or an sp3-hybridized carbon. All new compounds displayed high in vitro and in vivo antibacterial activity. Potency relative to the standard nitrogenated agents was dependent on ring size and hybridization of the linking carbon atom of the side chain. Compounds with a 1,2,3,6-tetrahydro-4-pyridinyl substituent at C-7 were equipotent with their 1-piperazinyl analogs, whereas those having a 4-piperidinyl or a 3-amino-1-cyclopentenyl ring at C-7 were less active than the 1-piperazinyl or 3-amino-1-pyrrolidinyl substituted agents, respectively. This relative difference in antibacterial potency did not correlate with the observed activity against gyrase, where the majority of the new compounds were equally or more potent than their nitrogenated counterparts.