(2-amino-5-fluorophenyl)(4-chlorophenyl)methanone | 1841-49-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-amino-5-fluorophenyl)(4-chlorophenyl)methanone
• 英文别名: (2-Amino-5-fluorophenyl)-(4-chlorophenyl)methanone
• CAS: 1841-49-2
• 化学式: C₁₃H₉ClFNO
• 分子量: 249.672
• InChiKey: HHQSWIFBOBTBEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-amino-5-fluorophenyl)(4-chlorophenyl)methanone 在 potassium hydroxide 、 肼 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.54h， 生成 4-(5-(4-chlorophenyl)-3-(4-(4-chlorophenyl)-6-fluoro-2-oxo-1,2-dihydroquinolin-3-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-oxobutanoic acid
  参考文献：
  名称：

  Structure–Activity Relationships and Pharmacophore Model of a Noncompetitive Pyrazoline Containing Class of GluN2C/GluN2D Selective Antagonists

  摘要：

  Here we describe the synthesis and structure-activity relationship for a class of pyrazoline-containing dihydroquinolone negative allosteric modulators of the NMDA receptor that show strong subunit selectivity for GluN2C- and GluN2D-containing receptors over GluN2A- and GluN2B-containing receptors. Several members of this class inhibit NMDA receptor responses in the nanomolar range and are more than 50-fold selective over GluN1/GluN2A and GluN1/GluN2B NMDA receptors, as well as AMPA, kainate, GABA, glycine, nicotinic, serotonin, and purinergic receptors. Analysis of the purified enantiomers of one of the more potent and selective compounds shows that the S-enantiomer is both more potent and more selective than the R-enantiomer. The S-enantiomer had an IC50 of 0.17-0.22 mu M at GluN2D- and GluN2C-containing receptors, respectively, and showed over 70-fold selectivity over other NMDA receptor subunits. The subunit selectivity of this class of compounds should be useful in defining the role of GluN2C- and GluN2D-containing receptors in specific brain circuits in both physiological and pathophysiological conditions.

  DOI：

  10.1021/jm400652r
• 作为产物：
  描述：

  2-氨基-5-氟苯甲酸 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 4.17h， 生成 (2-amino-5-fluorophenyl)(4-chlorophenyl)methanone
  参考文献：
  名称：

  Structure–Activity Relationships and Pharmacophore Model of a Noncompetitive Pyrazoline Containing Class of GluN2C/GluN2D Selective Antagonists

  摘要：

  Here we describe the synthesis and structure-activity relationship for a class of pyrazoline-containing dihydroquinolone negative allosteric modulators of the NMDA receptor that show strong subunit selectivity for GluN2C- and GluN2D-containing receptors over GluN2A- and GluN2B-containing receptors. Several members of this class inhibit NMDA receptor responses in the nanomolar range and are more than 50-fold selective over GluN1/GluN2A and GluN1/GluN2B NMDA receptors, as well as AMPA, kainate, GABA, glycine, nicotinic, serotonin, and purinergic receptors. Analysis of the purified enantiomers of one of the more potent and selective compounds shows that the S-enantiomer is both more potent and more selective than the R-enantiomer. The S-enantiomer had an IC50 of 0.17-0.22 mu M at GluN2D- and GluN2C-containing receptors, respectively, and showed over 70-fold selectivity over other NMDA receptor subunits. The subunit selectivity of this class of compounds should be useful in defining the role of GluN2C- and GluN2D-containing receptors in specific brain circuits in both physiological and pathophysiological conditions.

  DOI：

  10.1021/jm400652r

文献信息

• Antiinflammatory agents. 3. Synthesis and pharmacological evaluation of 2-amino-3-benzoylphenylacetic acid and analogs
  作者：David A. Walsh、H. Wayne Moran、Dwight A. Shamblee、Ibrahim M. Uwaydah、William J. Welstead、Lawrence F. Sancilio、Warren N. Dannenburg

  DOI：10.1021/jm00377a001

  日期：1984.11

  A series of substituted derivatives of 2-amino-3-benzoylphenylacetic acid (amfenac) has been synthesized and evaluated for antiinflammatory, analgesic, and cyclooxygenase inhibiting activity. Several derivatives including 157 (4'-chloro), 158 (4'-bromo), and 182 (5-chloro, 4'-bromo) were more potent than indomethacin in these assays.

  已经合成了一系列2-氨基-3-苯甲酰基苯基乙酸（氨苯乙酸）的取代衍生物，并评估了它们的抗炎，止痛和环加氧酶活性。在这些测定中，包括157（4'-氯），158（4'-溴）和182（5-氯，4'-溴）的几种衍生物比消炎痛更有效。
• One‐Pot Synthesis of 2‐Aminobenzophenones from 2‐Alkynyl Arylazides Catalyzed by Pd and Cu Precursors
  作者：Fan Yang、Shijie Xu、Hui Fan、Xuechun Zhao、Xiaoxiang Zhang

  DOI：10.1002/ejoc.202100772

  日期：2021.8.26

  A novel, one-pot, three-step synthetic method to prepare 2-aminobenzophenones from 2-alkynyl arylazides has been disclosed. This reaction is catalyzed by palladium to form 3-hydroxy-3-phenylindolin-2-ones, which is followed by hydrolysis of amide bonds and copper-catalyzed decarboxylation to generate 2-aminobenzophenones. The desired products are afforded in moderate to good yields under mild reaction

  公开了一种从 2-炔基芳基叠氮化物制备 2-氨基二苯甲酮的新型一锅三步合成方法。该反应由钯催化形成 3-羟基-3-苯基吲哚-2-酮，随后酰胺键水解和铜催化脱羧生成 2-氨基二苯甲酮。在温和的反应条件下以中等至良好的产率得到所需产物。
• Asymmetric Reduction of 2-Aminobenzophenone Using Yeast, Rhodosporidium toruloides.
  作者：Masahiro KATO、Kazuo SASAHARA、Kiyoshige OCHI、Hiroyuki AKITA、Takeshi OISHI

  DOI：10.1248/cpb.39.2498

  日期：——

  (±)-N-Isonicotinoyl-2-amino-5-chlorobenzhydrol (1) is a rice plant growth regulator which shortens the second leaf sheaths. One of the enantiomers, (S)-1, was obtained by microbiological asymmetric reduction of 2-amino-5-chlorobenzophenone using Rhodosporidium toruloides followed by isonicotinoylation. Several substituted benzhydrol derivatives were also prepared by use of the same biological method and converted to N-isonicotinoyl compounds. The growth-regulating activities of these compounds were evaluated.

  (±)-N-异烟酰基-2-氨基-5-氯苯基醇 (1) 是一种水稻植物生长调节剂，可缩短第二片叶鞘。通过使用红酵母Rhodosporidium toruloides对2-氨基-5-氯苯酮进行微生物不对称还原，得到了其中一个对映体(S)-1，随后进行异烟酰化。还通过相同的生物方法制备了几种取代的苯基醇衍生物，并转化为N-异烟酰基化合物。对这些化合物的生长调节活性进行了评估。
• Polyurethane mit kovalent gebundenen Photoinitiatoreinheiten
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP0849300A1

  公开（公告）日：1998-06-24

  In Wasser im wesentlichen selbstdispergierbares Polyurethan, erhältlich durch Umsetzung von a) mindestens einem Polyisocyanat mit b) mindestens einem Polyol und c) mindestens einem Photoinitiator der allgemeinen Formel I wobei R für einen Rest der Formel II oder für -CR7R8R9, P(=O)(R10)2 oder SO2R11 steht, wobei das Zahlenmittel des Molekulargewichts Mn des Polyurethans größer als 2700 ist, sowie dessen Verwendung. Weiterhin betrifft die Erfindung wäßrige Polyurethanharzdispersionen und Beschichtungsmittelzusammensetzungen, enthaltend die erfindungsgemäßen Polyurethane, sowie deren Verwendung.

  在水中基本自分散的聚氨酯，可通过以下反应获得 a) 至少一种多异氰酸酯与 b) 至少一种多元醇和 c) 至少一种通式 I 的光引发剂 其中 R 是式 II 的基团 或-CR7R8R9、P(=O)(R10)2 或 SO2R11、 其中聚氨酯的平均分子量 Mn 大于 2700。本发明还涉及含本发明聚氨酯的水性聚氨酯树脂分散体和涂料组合物及其用途。
• Synthesis of New Highly Functionalized Quinolines via a Novel FeIII-Catalyzed Domino aza-Michael/Aldol/Aromatization Reaction
  作者：Svetlana B. Tsogoeva、Felix Heckmann、Mohammad M. Ibrahim、Frank Hampel

  DOI：10.1055/s-0042-1751546

  日期：——

  We report the development of a straightforward, waste-reducing, environmentally friendly, FeIII-catalyzed domino aza-Michael/aldol/aromatization reaction in the presence of water to access high-value functionalized quinolines by using 2-aminobenzophenones and ethyl buta-2,3-dienoate as starting compounds. The tangible advantages, that is, the utilization of commercially available and/or easily accessible

  我们报告了一种直接、减少废物、环境友好、Fe III催化的多米诺氮杂-迈克尔/醇醛/芳构化反应的开发，该反应在水存在下通过使用 2-氨基二苯甲酮和乙基丁二酮获得高价值的官能化喹啉,3-二烯酸酯作为起始化合物。明显的优势，即利用市售和/或易于获得的底物、简单、温和的反应条件以及水作为溶剂的应用，使得这种三步多米诺骨牌工艺变得绿色，并且对于直接构建多米诺骨牌非常有吸引力。多种高功能化喹啉，产率高达 78%。