4-氯-8-氟-2-甲基喹啉 | 18615-59-3

• 物质功能分类: 医药中间体 - 杂环化合物
• 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: 4-氯-8-氟-2-甲基喹啉
• 英文名称: 8-Fluor-4-chlor-2-methyl-chinolin
• 英文别名: 4-chloro-8-fluoro-quinaldine；4-Chloro-8-fluoro-2-methylquinoline
• CAS: 18615-59-3
• 化学式: C₁₀H₇ClFN
• mdl: MFCD00272335
• 分子量: 195.624
• InChiKey: PKLIYBDVJXLAHP-UHFFFAOYSA-N

物化性质

• 沸点：
  269.9±35.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  常温常压下稳定，应避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22,R41
• WGK Germany：
  3
• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  4-氯-8-氟-2-甲基喹啉 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 N1-{4-[(10S)-dihydroartemisinin-10-oxyl]}phenylmethylene-N2-(8-fluoro-2-methylquinoline-4-yl)hydrazine
  参考文献：
  名称：

  N 1-{4-[(10S)-Dihydroartemisinin-10-oxyl]}phenylmethylene-N 2-(2-methylquinoline-4-yl)hydrazine derivatives as antiplasmodial falcipain-2 inhibitors

  摘要：

  A series of N (1)-{4-[(10S)-dihydroartemisinin-10-oxyl]}phenylmethylene-N (2)-(2-methylquinoline-4-yl) hydrazine derivatives 9a-9n possessing 4-quinolylhydrazone and artemisinin cores were herein synthesized and evaluated for their activities against cysteine protease falcipain-2 of Plasmodium falciparum. The structures were clearly confirmed by elemental analysis, H-1 NMR, and mass spectra. The pharmacological results indicated that all compounds showed excellent activity against recombinant falcipain-2 (IC50 = 0.15-2.28 mu M). The best one of this series was compound 9d (IC50 = 0.15 mu M). The molecular docking results showed that the compound 9d made close contact with the key active site of cysteine protease falcipain-2.

  DOI：

  10.1007/s00044-011-9854-3
• 作为产物：
  描述：

  8-氟-4-羟基-2-甲基喹啉 在 三氯氧磷 作用下， 反应 3.0h， 生成 4-氯-8-氟-2-甲基喹啉
  参考文献：
  名称：

  N 1-{4-[(10S)-Dihydroartemisinin-10-oxyl]}phenylmethylene-N 2-(2-methylquinoline-4-yl)hydrazine derivatives as antiplasmodial falcipain-2 inhibitors

  摘要：

  A series of N (1)-{4-[(10S)-dihydroartemisinin-10-oxyl]}phenylmethylene-N (2)-(2-methylquinoline-4-yl) hydrazine derivatives 9a-9n possessing 4-quinolylhydrazone and artemisinin cores were herein synthesized and evaluated for their activities against cysteine protease falcipain-2 of Plasmodium falciparum. The structures were clearly confirmed by elemental analysis, H-1 NMR, and mass spectra. The pharmacological results indicated that all compounds showed excellent activity against recombinant falcipain-2 (IC50 = 0.15-2.28 mu M). The best one of this series was compound 9d (IC50 = 0.15 mu M). The molecular docking results showed that the compound 9d made close contact with the key active site of cysteine protease falcipain-2.

  DOI：

  10.1007/s00044-011-9854-3

文献信息

• Quinoline–galactose hybrids bind selectively with high affinity to a galectin-8 N-terminal domain
  作者：Kumar Bhaskar Pal、Mukul Mahanti、Xiaoli Huang、Stella Persson、Anders P. Sundin、Fredrik R. Zetterberg、Stina Oredsson、Hakon Leffler、Ulf J. Nilsson

  DOI：10.1039/c8ob01354c

  日期：——

  structure-stabilizing water-mediated hydrogen bonds. The compounds were demonstrated to be non-toxic in an MTT assay with several breast cancer cell lines and one normal cell line. The improved affinity, selectivity, and low cytotoxicity suggest that the quinoline–galactoside derivatives provide an attractive starting point for the development of galectin-8N inhibitors potentially interfering with pathological

  喹啉，吲哚嗪和香豆素是许多生物活性分子中众所周知的结构元素。在本报告中，我们已经开发出了简单的方法，可以在可靠的反应条件下将喹啉，吲哚嗪和香豆素结构掺入半乳糖苷衍生物中，从而发现半乳糖凝集素家族蛋白的拟糖类抑制剂，这些抑制剂涉及免疫学和促进肿瘤的生物学过程。喹啉，吲哚嗪和香豆素衍生的半乳糖苷作为人galectin-1、2、3、4N（N末端结构域），4C（C末端结构域），7、8N，8C，9N和9C的抑制剂的评估揭示了喹啉衍生物可选择性结合半乳凝素galectin-8N，该半乳凝素在淋巴管生成，肿瘤进展和自噬中起关键作用，D-吡喃半乳糖苷。分子动力学模拟提出了一种相互作用模式，其中Arg59移动了2.5Å，并且抑制剂羧酸盐和喹啉氮形成了稳定结构的水介导的氢键。在具有几种乳腺癌细胞系和一种正常细胞系的MTT分析中，该化合物被证明是无毒的。改善的亲和力，选择性和低细胞毒性表明，喹啉-半乳糖苷衍生物
• COMPOSITIONS AND METHODS FOR MODULATING GATED ION CHANNELS
  申请人：VOHRA Rahul

  公开号：US20090023773A1

  公开（公告）日：2009-01-22

  Disclosed are compounds that modulate the activity of the gated ion channels. Compounds that modulate these gated ion channels are useful in the treatment of diseases and disorders related to pain, inflammation, the neurological system, the gastrointestinal system and genitourinary system. Preferred compounds include compounds of the Formulae 1, 2, 3, 4, and 5.

  本文披露了调节门控离子通道活性的化合物。调节这些门控离子通道的化合物在治疗与疼痛、炎症、神经系统、胃肠系统和泌尿系统相关的疾病和障碍方面具有用处。优选化合物包括式1、2、3、4和5的化合物。
• 4-BENZYLAMINOQUINOLINES, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, AND THEIR USE IN THERAPY
  申请人：Amberg Wilhelm

  公开号：US20100222346A1

  公开（公告）日：2010-09-02

  The present invention relates to 4-benzylaminoquinolines of the formula (I) or physiologically tolerated salts thereof. The invention relates to pharmaceutical compositions comprising such quinolines, and the use of such quinolines for therapeutic purposes. The quinolines are GIyTI inhibitors.

  本发明涉及式（I）的4-苄氨基喹啉或其生理上可耐受的盐。本发明涉及包含这种喹啉的药物组合物，以及使用这种喹啉进行治疗目的的方法。这些喹啉是GIyTI抑制剂。
• 4-benzylaminoquinolines, pharmaceutical compositions containing them, and their use in therapy
  申请人：Amberg Wilhelm

  公开号：US08420670B2

  公开（公告）日：2013-04-16

  The present invention relates to 4-benzylaminoquinolines of the formula (I) or physiologically tolerated salts thereof. The invention relates to pharmaceutical compositions comprising such quinolines, and the use of such quinolines for therapeutic purposes. The quinolines are GIyTI inhibitors.

  本发明涉及式(I)的4-苄基氨基喹啉或其生理上可耐受的盐。本发明涉及包含这样的喹啉的药物组合物，以及使用这样的喹啉进行治疗目的。这些喹啉是GIyTI抑制剂。
• [EN] QUINOLINE COMPOUNDS FOR INCREASING INSULINE RELEASE<br/>[FR] COMPOSÉS DE QUINOLÉINE POUR AUGMENTER LA LIBÉRATION D'INSULINE
  申请人：MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WSS E V

  公开号：WO2017198756A1

  公开（公告）日：2017-11-23

  The present invention relates to a class of quinoline compounds that act as insulin secretagogues, i.e., induce insulin secretion from beta cells. The present compounds may be used to induce divalent calcium cation influx in pancreatic beta-cells or to activate voltage-dependent calcium channels in pancreatic beta-cells. The present invention further relates to compounds for use in the treatment of diabetes.

  本发明涉及一类喹啉化合物，其作为胰岛素分泌素，即从β细胞中诱导胰岛素分泌。本化合物可用于诱导胰岛β细胞中的二价钙阳离子通量或激活胰岛β细胞中的电压依赖性钙通道。本发明还涉及用于治疗糖尿病的化合物。