4-ethylquinoline-N-oxide | 126921-53-7

• 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: 4-ethylquinoline-N-oxide
• 英文别名: 4-Ethyl-1-oxo-1lambda~5~-quinoline；4-ethyl-1-oxidoquinolin-1-ium
• CAS: 126921-53-7
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: UCLOONHUSMFODC-UHFFFAOYSA-N

物化性质

• 熔点：
  1200 °C(Solv: benzene (71-43-2))
• 沸点：
  324.4±35.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  25.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-ethylquinoline-N-oxide 在 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以38%的产率得到2-chloro-4-ethylquinoline
  参考文献：
  名称：

  6-Acylamino-2-aminoquinolines as Potent Melanin-Concentrating Hormone 1 Receptor Antagonists. Identification, Structure−Activity Relationship, and Investigation of Binding Mode

  摘要：

  Novel 6-acylamino-2-aminoquinoline melanin-concentrating hormone 1 receptor (MCHIR) antagonists were identified by sequential in silico screening with 3D pharmacophore models derived from a series of benzamide antagonists. The structure- activity relationship exploration by synthesis of analogues found structural demands around the western part of the compounds to be quite specific, whereas much structural freedom was found in the eastern part. Vvhile these compounds in general suffered from poor solubility properties, the 4-trifluoromethoxy-phenoxyacetamide western appendage provided a favorable combination of activity and solubility properties. The amine in the eastern appendage, originally required by the pharmacophore model and believed to interact with Asp123 in transmembrane 3 of MCH1R, could be removed without diminishing affinity or functional activity of the compounds. Docking studies suggested that the Asp123 interacts preferentially with the nitrogen of the central quinoline. Synthesis and testing of specific analogues supported our revised binding mode hypothesis.

  DOI：

  10.1021/jm050103y
• 作为产物：
  描述：

  4-甲基喹啉 在 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 氯仿 为溶剂， 反应 4.5h， 生成 4-ethylquinoline-N-oxide
  参考文献：
  名称：

  6-Acylamino-2-aminoquinolines as Potent Melanin-Concentrating Hormone 1 Receptor Antagonists. Identification, Structure−Activity Relationship, and Investigation of Binding Mode

  摘要：

  Novel 6-acylamino-2-aminoquinoline melanin-concentrating hormone 1 receptor (MCHIR) antagonists were identified by sequential in silico screening with 3D pharmacophore models derived from a series of benzamide antagonists. The structure- activity relationship exploration by synthesis of analogues found structural demands around the western part of the compounds to be quite specific, whereas much structural freedom was found in the eastern part. Vvhile these compounds in general suffered from poor solubility properties, the 4-trifluoromethoxy-phenoxyacetamide western appendage provided a favorable combination of activity and solubility properties. The amine in the eastern appendage, originally required by the pharmacophore model and believed to interact with Asp123 in transmembrane 3 of MCH1R, could be removed without diminishing affinity or functional activity of the compounds. Docking studies suggested that the Asp123 interacts preferentially with the nitrogen of the central quinoline. Synthesis and testing of specific analogues supported our revised binding mode hypothesis.

  DOI：

  10.1021/jm050103y

文献信息

• N-substituted-2-aminoquinolines useful for treating hypofunction of the
  申请人：American Home Products Corporation

  公开号：US05093333A1

  公开（公告）日：1992-03-03

  The compound of the formula: ##STR1## wherein R.sup.1 is H, alkyl or cycloalkyl of 1 to 6 carbon atoms; R.sup.2 is H, alkyl of 1 to 6 carbon atoms, cyano, halo, nitro, amino or mono or dialkylamino in which the alkyl groups have 1 to 6 carbon atoms; R.sup.3 is H or alkyl of 1 to 6 carbon atoms; n is 1 to 5 and R.sup.4 and R.sup.5 taken with the nitrogen atom to which they are attached are polymethylene of 4 to 6 carbon atoms, morpholino, pyrrolidin-2-on-1-yl, or a piperazin-1-yl moiety in the 4-position of which is H, alkyl of 1 to 6 carbon atoms or unsubstituted or substituted pyrimidinyl, pyridinyl, or pyrazinyl wherein the substituents are alkyl of 1 to 6 carbon atoms, alkoxyl of 1 to 6 carbon atoms, halo, cyano, nitro or trifluoromethyl and the pharmaceutically acceptable salts, hydrates and solvates thereof are M.sub.1 receptor agonists useful in treatment of dementias involving the cholinergic system.

  该化合物的化学式为：##STR1## 其中，R.sup.1是H，烷基或1到6个碳原子的环烷基；R.sup.2是H，1到6个碳原子的烷基，氰基，卤素，硝基，氨基或1到6个碳原子的烷基组成的单或双烷基氨基；R.sup.3是H或1到6个碳原子的烷基；n为1到5，R.sup.4和R.sup.5与它们连接的氮原子一起是4到6个碳原子的聚亚甲基，吗啡啉，吡咯烷-2-酮-1-基，或者是在4位上带有H，1到6个碳原子的烷基或未取代或取代的嘧啶基，吡啶基或吡嗪基，其中取代基是1到6个碳原子的烷基，1到6个碳原子的烷氧基，卤素，氰基，硝基或三氟甲基，以及其药学上可接受的盐，水合物和溶剂化合物是M.sub.1受体激动剂，用于治疗涉及胆碱系统的痴呆症。
• External oxidant-free alkylation of quinoline and pyridine derivatives
  作者：Linhua Shen、Xianying Gao、Nannan Luan、Zhenwei Liu、Jingya Li、Dapeng Zou、Yangjie Wu、Yusheng Wu

  DOI：10.1039/c9ob02653c

  日期：——

  A novel and efficient method for the generation of alkyl radicals and the alkylation of quinoline and pyridine derivatives under mild conditions has been developed. This strategy allows the direct alkylation of heteroaromatics in the absence of an external oxidant. A preliminary mechanistic study suggests that the present reaction probably proceeds via an intermolecular HAT process.

  已经开发了在温和条件下产生烷基自由基以及喹啉和吡啶衍生物烷基化的新颖有效的方法。该策略允许在没有外部氧化剂的情况下将杂芳族化合物直接烷基化。初步的机理研究表明，目前的反应可能是通过分子间的HAT过程进行的。
• Quinoline compounds for use in mch receptor related disorders
  申请人：Frimurer Michael Thomas

  公开号：US20060111357A1

  公开（公告）日：2006-05-25

  The present invention relates to the use of quinoline compounds for the preparation of a pharmaceutical and/or a cosmetic composition for the treatment, prophylaxis and/or diagnosis of a condition caused by or involving a melanin-concentrating hormone. The invention also relates to novel quinoline compounds per se. The quinoline compounds have been found to interact with a melanin-concentrating hormone receptor, a MCH receptor. The compounds have modulating activity on the MCH receptor such as e.g. antagonistic, agonistic or allosteric activity and are useful for medicinal or cosmetic purposes such as, e.g. in the treatment or prevention of feeding disorders like obesity, metabolic syndrome, Type II diabetes, bulimia, etc. or in the treatment or prevention of depression.

  本发明涉及使用喹啉化合物制备用于治疗、预防和/或诊断由或涉及黑色素浓缩激素引起的疾病的药物和/或化妆品组合物。本发明还涉及新型喹啉化合物本身。已发现喹啉化合物与黑色素浓缩激素受体（MCH受体）相互作用。该化合物对MCH受体具有调节活性，例如拮抗、激动或异构活性，并可用于药用或化妆品用途，例如治疗或预防饮食障碍，如肥胖症、代谢综合征、2型糖尿病、贪食症等，或治疗或预防抑郁症。
• QUINOLINE COMPOUNDS FOR USE IN MCH RECEPTOR RELATED DISORDERS
  申请人：7TM Pharma A/S

  公开号：EP1572212A2

  公开（公告）日：2005-09-14
• US4239897A
  申请人：——

  公开号：US4239897A

  公开（公告）日：1980-12-16