2-(2-甲基丙基)-4-喹啉羧酸 | 24260-31-9

• 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
• 中文名称: 2-(2-甲基丙基)-4-喹啉羧酸
• 英文名称: 2-isobutylquinoline-4-carboxylic acid
• 英文别名: 2-Isobutyl-cinchoninsaeure；2-Isobutyl-chinolin-4-carbonsaeure；2-Isobutyl-quinoline-4-carboxylic acid；2-(2-methylpropyl)quinoline-4-carboxylic acid
• CAS: 24260-31-9
• 化学式: C₁₄H₁₅NO₂
• mdl: MFCD01548753
• 分子量: 229.279
• InChiKey: FTAADMSZKWMHEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  2-(2-甲基丙基)-4-喹啉羧酸 在 乙醇 、 硫酸 作用下， 生成 2-isobutyl-quinoline-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  结核病的化学贡献I.亲水性，亲水性和亲水性延伸物的应用

  摘要：

  为了找到新的抗结核化合物，遵循了一个新的构想，制备了一些在2位取代的金鸡尼克酸系列的酰肼和。

  DOI：

  10.1002/hlca.19530360628
• 作为产物：
  描述：

  靛红 、 4-甲基-2-戊酮 在 氢氧化钾 、 盐酸 、 水 作用下， 以 乙醇 为溶剂， 反应 0.1h， 以42%的产率得到2-(2-甲基丙基)-4-喹啉羧酸
  参考文献：
  名称：

  新型2-咪唑啉酮和四氢嘧啶-2（1 H）-作为潜在的TACE抑制剂的研究：设计，合成，分子建模和初步生物学评估

  摘要：

  合成属于2-咪唑啉酮和四氢嘧啶-2（1 H）-一类的化合物，并评价其TACE抑制活性。大多数化合物显示出非常好的TACE抑制活性。对接研究清楚地表明了抑制剂的P1'基团对TACE抑制活性的重要性。这项工作证明这两类分子可用作开发TACE抑制剂的潜在先导。

  DOI：

  10.1016/j.bmc.2009.04.003

文献信息

• TRPM8 ANTAGONISTS AND THEIR USE IN TREATMENTS
  申请人：Biswas Kaustav

  公开号：US20130157996A1

  公开（公告）日：2013-06-20

  Compounds of Formula I are useful as antagonists of TRPM8. Such compounds are useful in treating a number of TRPM8 mediated disorders and conditions and may be used to prepare medicaments and pharmaceutical compositions useful for treating such disorders and conditions. Examples of such disorders include, but are not limited to, migraines and neuropathic pain. Compounds of Formula I have the following structure: where the definitions of the variables are provided herein.

  公式I的化合物可用作TRPM8的拮抗剂。这些化合物在治疗许多TRPM8介导的疾病和病症方面非常有用，并可用于制备用于治疗此类疾病和病症的药物和制剂。此类疾病的示例包括但不限于偏头痛和神经病性疼痛。公式I的化合物具有以下结构：其中变量的定义在此提供。
• Microwave‐Assisted Synthesis of Quinoline Derivatives from Isatin
  作者：El Sayed H. El Ashry、El Sayed Ramadan、Hamida Abdel Hamid、Mohamed Hagar

  DOI：10.1080/00397910500184719

  日期：2005.9.1

  Microwave irradiation has been used for a rapid and efficient synthesis of quinoline-4-carboxylic acids 5a-g and 1,2,3,4-tetrahydroacridine-9-carboxylic acid (6) from the reaction of isatins 1-3 with acyclic and cyclic ketones in basic medium. 2-Hydroxyquinoline-4-carboxylic acid (11) was also obtained by irradiating a mixture of isatin 1 and malonic acid in AcOH. The esters of 5f and 11 and their respective hydrazides 8 and 13 were also prepared under MWI.
• 26. The application of Pfitzinger reactions to the synthesis of quinoline derivatives: a novel route to 4-hydroxyquinolines
  作者：Ng. Ph. Buu-Hoï、René Royer

  DOI：10.1039/jr9480000106

  日期：——
• 5-HT3 Receptor antagonists. 3. Quinoline derivatives which may be effective in the therapy of irritable bowel syndrome
  作者：Nobuyuki Kishibayashi、Yoshikazu Miwa、Hiroaki Hayashi、Akio Ishii、Shunji Ichikawa、Hiromi Nonaka、Toshihide Yokoyama、Fumio Suzuki

  DOI：10.1021/jm00074a009

  日期：1993.10

  A series of quinolinecarboxylic acid derivatives has been previously described as a new class of 5-HT3 receptor antagonists due to deviation of a carbonyl moiety from the plane of an aromatic ring in their minimum-energy conformations. These derivatives were evaluated in a wrap-restraint stress-induced defecation model in rats. Reference compounds, ondansetron (1), granisetron (2), and YM060 (4), potently inhibited a stress-induced increase in stools excreted from fed rats (ID50 = 0.27, 0.12, and 0.0052 mg/kg, po, respectively). However, quinoline derivatives exhibited different activities depending on structural class. 4-Hydroxyquinoline-3-carboxylic acid derivatives 5 and 6a possess high affinity for the 5-HT3 receptor (K(i) = 6.1 and 1.5 nM, respectively) and exhibit potent activity in the Bezold-Jarisch (B-J) reflex test (ED50 = 0.0017 and 0.000 10 mg/kg, iv, respectively), but they did not effectively inhibit the increase in fecal pellet output at the dose of 1 mg/kg, po. On the other hand, most of 1-substituted 2-oxoquinoline-4-carboxylates 10 showed less potent activity in the B-J reflex test than 1 or 2 but inhibited restraint stress-induced defecation more potently than 1 or 2. The ID50 value of endo-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 1-isobutyl-2-oxo-1,2-dihydro-4-quinolinecarboxylate 10e was 0.013 mg/kg, po. With respect to the selected compounds 6a and 10e, effects on 5-HT- and thyrotropin-releasing hormone (TRH)-induced defecation, castor oil-induced diarrhea and wrap-restraint stress-induced colonic propulsion in rats were examined. These 5-HT3 receptor antagonists did not effectively inhibit castor oil-induced diarrhea, which has been reported not to be mediated via the 5-HT3 receptor. Although 10e showed 800-fold decreased potency compared with 4 in the B-J reflex test, 10e exhibited activity as potent as 4 in 5-HT- and TRH-induced defecation assays; 10e exhibited 7-fold increased potency compared with 4 in wrap-restraint stress-induced colonic propulsions. From these results, 10e appears to interact selectively with 5-HT3 receptors in the gastrointestinal system and might be effective in the therapy of irritable bowel syndrome (IBS).
• Doebner, Justus Liebigs Annalen der Chemie, 1887, vol. 242, p. 265
  作者：Doebner

  DOI：——

  日期：——