2-chloro-7-fluoro-8-methylquinoline-3-carboxaldehyde | 1167542-21-3

• 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-chloro-7-fluoro-8-methylquinoline-3-carboxaldehyde
• 英文别名: 2-chloro-7-fluoro-8-methylquinoline-3-carbaldehyde；2-Chloro-7-fluoro-8-methylquinoline-3-carbaldehyde
• CAS: 1167542-21-3
• 化学式: C₁₁H₇ClFNO
• 分子量: 223.634
• InChiKey: IDUAAKKFSBLOFD-UHFFFAOYSA-N

物化性质

• 沸点：
  353.4±37.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-7-fluoro-8-methylquinoline-3-carboxaldehyde 在 sodium tetrahydroborate 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成
  参考文献：
  名称：

  喹啉共轭 1,2,3-三唑衍生物作为杀虫剂的合成、生物学评价和分子对接研究

  摘要：

  在目前的工作中，我们从取代的乙酰苯胺开始，分五步合成了新型的喹啉共轭 1,2,3-三唑衍生物6a - l 。筛选合成的化合物的抗寄生虫活性。与喹啉结合的 1,2,3-三唑化合物6c (IC 50  = 15.1 μg/ml)、6d (IC 50  = 14.6 μg/ml) 和6e (IC 50  = 14.3 μg/ml) 与标准葡萄糖酸锑钠 (IC 50  = 14.3 ± 1.5 μg/ml)。利什曼原虫主要蝶啶还原酶（Lm）的分子对接研究-PTR1) 表明这些化合物有可能成为抗寄生虫药物发现的先导分子。

  DOI：

  10.1002/jhet.4414
• 作为产物：
  描述：

  3-氟-2-甲基苯胺 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 2-chloro-7-fluoro-8-methylquinoline-3-carboxaldehyde
  参考文献：
  名称：

  Synthesis and Herbicidal Activity of Triketone–Quinoline Hybrids as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

  摘要：

  4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) is one of the most important targets for herbicide discovery. In the search for new HPPD inhibitors with novel scaffolds, triketone-quinoline hybrids were designed and subsequently optimized on the basis of the structure -activity relationship (SAR) studies. Most of the synthesized compounds displayed potent inhibition of Arabidopsis thaliana HPPD (AtHPPD), and some of them exhibited broad-spectrum and promising herbicidal activity at the rate of 150 g ai/ha by postemergence application. Most promisingly, compound III-1, 3-hydroxy-2-(2-methoxy-7-(methylthio)quinoline-3-carbonyl)cyclohex-2-enone (K-i = 0.009 mu M, AtHPPD), had broader spectrum of weed control than mesotrione. Furthermore, compound III-1 was much safer to maize at the rate of 150 g ai/ha than mesotrione, demonstrating its great potential as herbicide for weed control in maize fields. Therefore, triketone-quinoline hybrids may serve as new lead structures for novel herbicide discovery.

  DOI：

  10.1021/acs.jafc.5b01530

文献信息

• [EN] FUSED PYRIDINE AND PYRAZINE DERIVATIVES AS KINASE INHIBITORS<br/>[FR] DÉRIVÉS CONDENSÉS DE PYRIDINE ET DE PYRAZINE EN TANT QU'INHIBITEURS DE KINASES
  申请人：UCB PHARMA SA

  公开号：WO2010092340A1

  公开（公告）日：2010-08-19

  A series of amino-substituted fused pyridine and pyrazine derivatives, in particular amino-substituted quinoline and quinoxaline derivatives, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

  一系列氨基取代的融合吡啶和吡嗪衍生物，特别是氨基取代的喹啉和喹喔啉衍生物，作为选择性PI3激酶酶抑制剂，在医学上具有益处，例如在治疗炎症性、自身免疫性、心血管、神经退行性、代谢性、肿瘤学、疼痛性或眼科疾病方面。
• [EN] TRIAZINE DERIVATIVES AS KINASE INHIBITORS<br/>[FR] DÉRIVÉS DE TRIAZINE EN TANT QU'INHIBITEURS DE KINASES
  申请人：UCB PHARMA SA

  公开号：WO2010100405A1

  公开（公告）日：2010-09-10

  A series of substituted [1,3,5]triazin-2-yl derivatives, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

  一系列取代的[1,3,5]三嗪-2-基衍生物，作为选择性PI3激酶酶抑制剂，在医学上具有益处，例如在治疗炎症性、自身免疫性、心血管、神经退行性、代谢性、肿瘤学、疼痛或眼科疾病方面。
• [EN] QUINOLINE AND QUINOXALINE DERIVATIVES AS KINASE INHIBITORS<br/>[FR] DÉRIVÉS DE QUINOLÉINE ET DE QUINOXALINE EN TANT QU'INHIBITEURS DE KINASE
  申请人：UCB PHARMA SA

  公开号：WO2011058108A1

  公开（公告）日：2011-05-19

  A series of quinoline and quinoxaline derivatives, substituted by an optionally substituted bicyclic heteroaryl moiety consisting of two fused six-membered aromatic rings attached via an alkylene chain optionally linked to a heteroatom, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

  一系列喹啉和喹啉衍生物，其取代的环异芳基部分由两个融合的六元芳香环组成，通过一个可选择连接到杂原子的烷基链连接，这些衍生物是选择性的PI3激酶酶抑制剂，在医学上具有益处，例如在治疗炎症、自身免疫、心血管、神经退行性、代谢、肿瘤、疼痛或眼科疾病方面。
• [EN] QUINOLINE AND QUINOXALINE DERIVATIVES AS KINASE INHIBITORS<br/>[FR] DÉRIVÉS DE QUINOLINE ET DE QUINOXALINE À TITRE D'INHIBITEURS DE KINASES
  申请人：UCB PHARMA SA

  公开号：WO2012032334A1

  公开（公告）日：2012-03-15

  A series of quinoline and quinoxaline derivatives comprising a fluorinated ethyl side-chain, being selective inhibitors of P13 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

  一系列含有氟乙基侧链的喹啉和喹啉衍生物，作为选择性P13激酶酶抑制剂，在医学上具有益处，例如在治疗炎症性、自身免疫性、心血管、神经退行性、代谢性、肿瘤学、疼痛或眼科疾病方面。
• [EN] FUSED BICYCLIC PYRIDINE AND PYRAZINE DERIVATIVES AS KINASE INHIBITORS<br/>[FR] DÉRIVÉS DE PYRIDINE ET DE PYRAZINE BICYCLIQUES CONDENSÉS COMME INHIBITEURS DE KINASES
  申请人：UCB PHARMA SA

  公开号：WO2011058113A1

  公开（公告）日：2011-05-19

  A series of fused bicyclic pyridine and pyrazine derivatives, substituted directly on the pyridine or pyrazine ring by a functional group attached via a sulphur-containing linkage, being selective inhibitors of P13 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

  一系列通过含硫键连接的功能基团直接取代吡啶或吡嗪环的融合双环吡啶和吡嗪衍生物，作为选择性P13激酶酶抑制剂，在医学上具有益处，例如在炎症、自身免疫、心血管、神经退行性、代谢、肿瘤、疼痛或眼科疾病的治疗中。