4-ethyl-2-(4-methylpiperazin-1-yl)-6-nitroquinoline | 710328-68-0

• 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-ethyl-2-(4-methylpiperazin-1-yl)-6-nitroquinoline
• CAS: 710328-68-0
• 化学式: C₁₆H₂₀N₄O₂
• 分子量: 300.36
• InChiKey: XQHHSMNUUXEXKL-UHFFFAOYSA-N

物化性质

• 沸点：
  492.5±45.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-ethyl-2-(4-methylpiperazin-1-yl)-6-nitroquinoline 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以84%的产率得到4-ethyl-2-(4-methylpiperazin-1-yl)quinolin-6-ylamine
  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：

  2-chloro-4-ethylquinoline 在 硝酸 作用下， 反应 17.0h， 生成 4-ethyl-2-(4-methylpiperazin-1-yl)-6-nitroquinoline
  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

• 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
• [EN] QUINOLINE COMPOUNDS FOR USE IN MCH RECEPTOR RELATED DISORDERS<br/>[FR] UTILISATION DE COMPOSES DE LA QUINOLINE POUR TRAITER DES TROUBLES LIES AU RECEPTEUR MCH
  申请人：7TM PHARMA AS

  公开号：WO2004052370A2

  公开（公告）日：2004-06-24

  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.
• [EN] CYCLIC QUINOLINE COMPOUNDS FOR USE IN MCH RECEPTOR RELATED DISORDERS<br/>[FR] COMPOSES DE QUINOLINE CYCLIQUES UTILISES AVEC DES TROUBLES LIES AU RECEPTEUR MCH
  申请人：7TM PHARMA AS

  公开号：WO2004052371A2

  公开（公告）日：2004-06-24

  The present invention relates to the use of cyclic 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 cyclic quinoline compounds per se . The cyclic 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. antagonisitic, 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.
• 6-Acylamino-2-aminoquinolines as Potent Melanin-Concentrating Hormone 1 Receptor Antagonists. Identification, Structure−Activity Relationship, and Investigation of Binding Mode
  作者：Trond Ulven、Thomas M. Frimurer、Jean-Marie Receveur、Paul Brian Little、Øystein Rist、Pia K. Nørregaard、Thomas Högberg

  DOI：10.1021/jm050103y

  日期：2005.9.1

  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.