2-phenethyl-quinoline-4-carboxylic acid | 222960-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-phenethyl-quinoline-4-carboxylic acid
• 英文别名: 2-Phenaethyl-chinolin-4-carbonsaeure；2-(beta-Phenylethyl)-4-quinolinecarboxylic acid；2-(2-phenylethyl)quinoline-4-carboxylic acid
• CAS: 222960-37-4
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: RPHNQBLSVQBAOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N,N'-三乙基乙二胺 、 2-phenethyl-quinoline-4-carboxylic acid 生成 2-phenethyl-quinoline-4-carboxylic acid-[ethyl-(2-diethylamino-ethyl)-amide]
  参考文献：
  名称：

  Unilaterally acylated diamines and process of making same

  摘要：

  公开号：

  US01886481A1
• 作为产物：
  描述：

  靛红 在 氢氧化钾 作用下， 生成 2-phenethyl-quinoline-4-carboxylic acid
  参考文献：
  名称：

  Borsche; Vorbach, Justus Liebigs Annalen der Chemie, 1939, vol. 537, p. 22,36

  摘要：

  DOI：

文献信息

• Mycobacterium tuberculosis Inhibitors Based on Arylated Quinoline Carboxylic Acid Backbones with Anti-Mtb Gyrase Activity
  作者：Mark Tristan J. Quimque、Adrian D. Go、Justin Allen K. Lim、Warren S. Vidar、Allan Patrick G. Macabeo

  DOI：10.3390/ijms241411632

  日期：——

  The present study profiles new arylated quinoline carboxylic acids (QCAs) having activity against replicating and non-replicating Mycobacterium tuberculosis (Mtb), the causative agent of TB. Thus, the synthesis, characterization, and in vitro screening (MABA and LORA) of 48 QCAs modified with alkyl, aryl, alkoxy, halogens, and nitro groups in the quinoline ring led to the discovery of two QCA derivatives

  迫切需要具有新作用模式或新抑制模式的新型抗结核药物来克服耐药结核病（TB）的威胁。本研究描述了新型芳基化喹啉羧酸 (QCA)，其具有对抗复制型和非复制型结核分枝杆菌 (Mtb)（结核病病原体）的活性。因此，对喹啉环中烷基、芳基、烷氧基、卤素和硝基修饰的 48 个 QCA 进行合成、表征和体外筛选（MABA 和 LORA），最终发现了两种 QCA 衍生物 7i 和 7m，其中C-2 2-(萘-2-基)/C-6 1-丁基和C-2 22-(菲-3-基)/C-6 异丙基分别是最好的Mtb抑制剂。两者均表现出 DNA 旋转酶抑制作用，其中 QCA 7m 在高达 1 μM 的测试浓度下表现出更好的活性。最后，开发了两种化合物与 Mtb DNA 旋转酶的对接模型，并显示出与体外结果良好的相关性。
• DE540697
  申请人：——

  公开号：——

  公开（公告）日：——
• John, Journal fur praktische Chemie (Leipzig 1954), 1927, vol. <2> 117, p. 222
  作者：John

  DOI：——

  日期：——
• Crippa; Scevola, Gazzetta Chimica Italiana, 1937, vol. 67, p. 119,120
  作者：Crippa、Scevola

  DOI：——

  日期：——
• NOVEL MYCOBACTERIAL INHIBITORS
  申请人：Guillemont Emile Georges Jerome

  公开号：US20070299106A1

  公开（公告）日：2007-12-27

  The present invention relates to novel substituted quinoline derivatives according to the general Formula (I) pharmaceutically acceptable addition salts, quaternary amines, stereochemically isomeric forms, tautomeric forms and N-oxide forms thereof, wherein R 1 is hydrogen, halo, haloalkyl, cyano, hydroxy, Ar, Het, alkyl, alkyloxy, alkylthio, alkyloxyalkyl, alkylthioalkyl, Ar-alkyl or di(Ar)alkyl; p is 1, 2 or 3; s is 0, 1, 2, 3 or 4; R 2 is hydrogen; halo; alkyl; hydroxy; mercapto; optionally substituted alkyloxy; alkyloxyalkyloxy; alkylthio; mono or di(alkyl)amino wherein alkyl may optionally be substituted; Ar; Het, a radical of formula R 3 is alkyl, Ar, Ar-alkyl, Het, Het-alkyl; q is 0, 1, 2, 3 or 4; R 4 and R 5 are hydrogen, alkyl, benzyl; or R 4 and R 5 may be taken together including the N to which they are attached; R 6 is hydrogen, halo, haloalkyl, hydroxy, Ar, alkyl, alkyloxy, alkylthio, alkyloxyalkyl, alkylthioalkyl, Ar-alkyl or di(Ar)alkyl; or two vicinal R 6 radicals may be taken together to form together with the phenyl ring to which they are attached a naphthyl; r is 1, 2, 3, 4 or 5; R 7 is hydrogen, alkyl, Ar or Het; R 8 is hydrogen-, alkyl, hydroxyl, aminocarbonyl, mono-or di(alkyl)aminocarbonyl, Ar, Het, substituted alkyl, Het-C(═O)— or Ar—C(═O)—; provided that when the quinoline substituent carrying the R 3 to R 6 substituents is placed in position 3 of the quinoline moiety; R 7 is placed in position 4 and R 2 is placed in position 2 and represents hydrogen, hydroxy, mercapto, alkyloxy, alkyloxyalkyloxy, alkylthio, mono or di(alkyl)amino or a radical of formula then s is 1, 2, 3 or 4; also claimed is a composition comprising the claimed compounds, the use of the claimed compounds or compositions for the manufacture of a medicament for the treatment of mycobacterial diseases and a process for preparing the claimed compounds.