ethyl 2-(3-chloro-6-nitro-2,4,5-trifluorobenzoyl)acetate | 111230-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-(3-chloro-6-nitro-2,4,5-trifluorobenzoyl)acetate
• 英文别名: ethyl 3-chloro-2,4,5-trifluoro-6-nitrobenzoylacetate；ethyl (3-chloro-2,4,5-trifluoro-6-nitro)-β-oxophenylpropanoate；ethyl 3-(3-chloro-2,4,5-trifluoro-6-nitrophenyl)-3-oxopropanoate
• CAS: 111230-50-3
• 化学式: C₁₁H₇ClF₃NO₅
• 分子量: 325.628
• InChiKey: MZSMCLGNJHSWEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  412.6±45.0 °C(Predicted)
• 密度：
  1.547±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3-chloro-6-nitro-2,4,5-trifluorobenzoyl)acetate 在 盐酸 、 乙酸酐 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 8.5h， 生成 洛美沙星杂质
  参考文献：
  名称：

  Synthesis and biological activity of 5-amino- and 5-hydroxyquinolones, and the overwhelming influence of the remote N1-substituent in determining the structure-activity relationship

  摘要：

  A series of 5-amino- and 5-hydroxyquinolone antibacterials substituted at C7 with a select group of common piperazinyl and 3-aminopyrrolidinyl side chains was prepared. These 5-substituted derivatives were compared to the analogous 5-hydrogen compounds for antiinfective activity by using DNA gyrase inhibition, minimum inhibitory concentrations against a variety of bacteria, and in vivo efficacy in the mouse infection model. The influence on the structure-activity relationships of varied substituents at C8 (H, F, Cl) and Ni (ethyl, cyclopropyl, difluorophenyl) was also studied. The results showed that several of the structure-activity conclusions regarding side-chain bulk at C7, the effect of halogen at C8, and the effect of the C5-amino group were greatly influenced by the choice of the N1-substituent. Several outstanding broad spectrum quinolones were identified in this work. In particular, the spectrum and potency of the 7-piperazinyl quinolones could be greatly enhanced by the judicious choice of C5-, C8-, and N1-substitutents.

  DOI：

  10.1021/jm00107a039
• 作为产物：
  描述：

  3-氯-2,4,5-三氟-6-硝基苯甲酸 在 正丁基锂 、 dipyridyl 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 ethyl 2-(3-chloro-6-nitro-2,4,5-trifluorobenzoyl)acetate
  参考文献：
  名称：

  Synthesis and biological activity of 5-amino- and 5-hydroxyquinolones, and the overwhelming influence of the remote N1-substituent in determining the structure-activity relationship

  摘要：

  A series of 5-amino- and 5-hydroxyquinolone antibacterials substituted at C7 with a select group of common piperazinyl and 3-aminopyrrolidinyl side chains was prepared. These 5-substituted derivatives were compared to the analogous 5-hydrogen compounds for antiinfective activity by using DNA gyrase inhibition, minimum inhibitory concentrations against a variety of bacteria, and in vivo efficacy in the mouse infection model. The influence on the structure-activity relationships of varied substituents at C8 (H, F, Cl) and Ni (ethyl, cyclopropyl, difluorophenyl) was also studied. The results showed that several of the structure-activity conclusions regarding side-chain bulk at C7, the effect of halogen at C8, and the effect of the C5-amino group were greatly influenced by the choice of the N1-substituent. Several outstanding broad spectrum quinolones were identified in this work. In particular, the spectrum and potency of the 7-piperazinyl quinolones could be greatly enhanced by the judicious choice of C5-, C8-, and N1-substitutents.

  DOI：

  10.1021/jm00107a039

文献信息

• [EN] QUINOLIN-4-ONE AND 4(1H)-CINNOLINONE COMPOUNDS AND METHODS OF USING SAME<br/>[FR] COMPOSÉS DE QUINOLIN-4-ONE ET DE 4(1H)-CINNOLINONE ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：FREQUENCY THERAPEUTICS INC

  公开号：WO2020163816A1

  公开（公告）日：2020-08-13

  The present disclosure relates to quinolin-4-one and 4(1H)-cinnolinone compounds and methods of using them to induce self-renewal of stem/progenitor supporting cells, including inducing the stem/progenitor cells to proliferate while maintaining, in the daughter cells, the capacity to differentiate into tissue cells.

  本公开涉及喹啉-4-酮和4(1H)-喹啉酮化合物，以及使用它们诱导干/祖细胞支持细胞自我更新的方法，包括诱导干/祖细胞增殖，同时在子细胞中保持分化为组织细胞的能力。
• NOVEL PYRIDONECARBOXYLIC ACID DERIVATIVE OR SALT THEREOF
  申请人：WAKUNAGA PHARMACEUTICAL CO., LTD.

  公开号：US20190276407A1

  公开（公告）日：2019-09-12

  A pyridonecarboxylic acid derivative or a salt thereof is represented by Formula (1), where R 1 is hydrogen, a halogen atom, a lower alkyl group, or an amino group; R 2 is —NH—R 6 , where R 6 is hydrogen, a lower alkyl group, an amino lower alkyl group, or the like; —O—R 7 , where R 7 is hydrogen, a lower alkyl group, or the like; —(CH 2 ) m —R 8 , where R 8 is an amino group or the like, m is 1, 2, 3 or 4; or a cyclic amino group of Formula (2), where Y represents NH or C—R 9a R 9b , where R 9a and R 9b are each independently hydrogen, a lower alkyl group, an amino group, a lower alkyl amino group, or the like; n and p are 1 or 2; R 3 is hydrogen, a halogen atom, a lower alkyl group, or the like; R 4 is hydrogen or a carboxyl group-protecting group; and R 5 is hydrogen or a hydroxyl group-protecting group.

  化合物或其盐可由以下式（1）表示，其中R1是氢、卤素原子、低烷基或氨基；R2是—NH—R6，其中R6是氢、低烷基、氨基低烷基或类似物；—O—R7，其中R7是氢、低烷基或类似物；—(CH2)m—R8，其中R8是氨基或类似物，m为1、2、3或4；或由以下式（2）的环状氨基团表示，其中Y代表NH或C—R9aR9b，其中R9a和R9b各自独立地是氢、低烷基、氨基、低烷基氨基或类似物；n和p为1或2；R3是氢、卤素原子、低烷基或类似物；R4是氢或羧基保护基团；R5是氢或羟基保护基团。
• 5-amino and 5-hydroxy-6-fluoroquinolones as antibacterial agents
  申请人：Warner-Lambert Company

  公开号：US04977154A1

  公开（公告）日：1990-12-11

  Novel 7-piperazine derivatives of 5-amino- and 5-hydroxy-1-cyclopropyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections.

  本发明涉及7-哌嗪衍生物的新型抗菌剂，其基础结构为5-氨基-和5-羟基-1-环丙基-1,4-二氢-4-氧喹啉-3-羧酸，并描述了它们的制备方法、配方和用于治疗细菌感染的用途。
• Pyridonecarboxylic acid derivatives or their salts and antibacterial
  申请人：Wakunaga Pharmaceuticals Co., Ltd.

  公开号：US05998436A1

  公开（公告）日：1999-12-07

  A pyridonecarboxylic acid derivative represented by the following general formula (1): ##STR1## [wherein R.sup.1 represents hydrogen atom or a carboxyl protective group; R.sup.2 represents hydroxyl group, a lower alkoxy group, or a substituted or unsubstituted amino group; R.sup.3 represents hydrogen atom or a halogen atom; R.sup.4 represents hydrogen atom or a halogen atom; R.sup.5 represents a halogen atom or an optionally substituted saturated cyclic amino group; R.sup.6 represents hydrogen atom, a halogen atom, nitro group, or an optionally protected amino group; X, Y and Z may be the same or different and respectively represent nitrogen atom, --CH.dbd. or --CR.sup.7 .dbd. (wherein R.sup.7 represents a lower alkyl group, a halogen atom, or cyano group) (with the proviso that at least one of X, Y and Z represent the nitrogen atom), and W represents nitrogen atom or --CR.sup.8 .dbd. (wherein R.sup.8 represents hydrogen atom, a halogen atom, or a lower alkyl group)] or its salt, as well as an antibacterial agent containing such compound are provided.

  提供一种由以下一般式（1）表示的吡啶酮羧酸衍生物：##STR1## [其中R.sup.1表示氢原子或羧基保护基；R.sup.2表示羟基，较低的烷氧基或取代或未取代的氨基；R.sup.3表示氢原子或卤素原子；R.sup.4表示氢原子或卤素原子；R.sup.5表示卤素原子或可选择取代的饱和环氨基；R.sup.6表示氢原子，卤素原子，硝基或可选择保护的氨基；X，Y和Z可以相同或不同，分别表示氮原子，--CH.dbd.或--CR.sup.7.dbd.（其中R.sup.7表示较低的烷基，卤素原子或氰基）（具有至少一个X，Y和Z表示氮原子的条件），W表示氮原子或--CR.sup.8.dbd.（其中R.sup.8表示氢原子，卤素原子或较低的烷基）]或其盐，以及含有这种化合物的抗菌剂。
• Pyridonecarboxylic acid derivatives or their salts, and antibacterial
  申请人：Wakunaga Pharmaceutical Co., Ltd.

  公开号：US06133284A1

  公开（公告）日：2000-10-17

  A pyridonecarboxylic acid derivative represented by the following general formula (1): ##STR1## [wherein R.sup.1 represents hydrogen atom or a carboxyl protective group; R.sup.2 represents hydroxyl group, a lower alkoxy group, or a substituted or unsubstituted amino group; R.sup.3 represents hydrogen atom or a halogen atom; R.sup.4 represents hydrogen atom or a halogen atom; R.sup.5 represents a halogen atom or an optionally substituted saturated cyclic amino group; R.sup.6 represents hydrogen atom, a halogen atom, nitro group, or an optionally protected amino group; X, Y and Z may be the same or different and respectively represent nitrogen atom, --CH.dbd. or --CR.sup.7 .dbd. (wherein R.sup.7 represents a lower alkyl group, a halogen atom, or cyano group) (with the proviso that at least one of X, Y and Z represent the nitrogen atom), and W represents nitrogen atom or --CR.sup.8 .dbd. (wherein R.sup.8 represents hydrogen atom, a halogen atom, or a lower alkyl group)] or its salt, as well as an antibacterial agent containing such compound are provided.

  提供一种由以下通式（1）表示的吡啶酮羧酸衍生物：##STR1## [其中，R.sup.1表示氢原子或羧基保护基；R.sup.2表示羟基、低级烷氧基或取代或未取代的氨基；R.sup.3表示氢原子或卤素原子；R.sup.4表示氢原子或卤素原子；R.sup.5表示卤素原子或可选取代的饱和环氨基基团；R.sup.6表示氢原子、卤素原子、硝基基团或可选保护的氨基基团；X、Y和Z可以相同也可以不同，分别表示氮原子、--CH.dbd.或--CR.sup.7.dbd.（其中，R.sup.7表示低级烷基、卤素原子或氰基）（但至少其中一个为氮原子），W表示氮原子或--CR.sup.8.dbd.（其中，R.sup.8表示氢原子、卤素原子或低级烷基）]或其盐，以及含有此类化合物的抗菌剂。