4-methyl-2-(4-methylpiperazin-1-yl)-6-nitroquinoline | 705271-37-0

• 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-methyl-2-(4-methylpiperazin-1-yl)-6-nitroquinoline
• CAS: 705271-37-0
• 化学式: C₁₅H₁₈N₄O₂
• 分子量: 286.334
• InChiKey: QZDDHVIZYYENQF-UHFFFAOYSA-N

物化性质

• 熔点：
  155-160 °C
• 沸点：
  483.7±45.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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-methyl-2-(4-methylpiperazin-1-yl)-6-nitroquinoline 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 4-methyl-2-(4-methylpiperazin-1-yl)quinolin-6-ylamine
  参考文献：
  名称：

  Identification and optimization of novel 6-acylamino-2-aminoquinolines as potent Hsp90 C-terminal inhibitors

  摘要：

  In order to discover novel Hsp90 inhibitors targeting the C-terminal ATP binding pocket, a novobiocin derivative based ROCS model was constructed for virtual screening. Compound 13 was identified as the lead compound and then systematical structure activity relationship (SAR) study was conducted. These efforts led to compound 69, which exhibited potent anti-proliferative activities against MCF7 and SKBr3 breast cancer cell lines. In 4T1 mice breast cancer models, 69 exhibited potent tumor growth inhibition and anti-metastasis effect. Compound 69 as a potent antitumor agent targeting the Hsp90 C-terminal is worthy of further pre-clinical study. (C) 2017 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2017.07.080
• 作为产物：
  描述：

  4-甲基-2-氯-喹啉 在 硝酸 作用下， 反应 17.0h， 生成 4-methyl-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。
• Structure–activity relationships of a novel series of melanin-concentrating hormone (MCH) receptor antagonists
  作者：Rosa Arienzo、David E Clark、Sue Cramp、Stephen Daly、Hazel J Dyke、Peter Lockey、Dennis Norman、Alan G Roach、Keith Stuttle、Maxine Tomlinson、Melanie Wong、Stephen P Wren

  DOI：10.1016/j.bmcl.2004.05.051

  日期：2004.8

  A new series of 2-aminoquinolines has been identified as antagonists of the melanin concentrating hormone receptor (MCH-1R). Syntheses and structure-activity relationships are described leading to a compound having low nanomolar activity against the receptor and demonstrating functional antagonism. Studies also showed that some of the compounds were selective against a range of other G protein-coupled receptors. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.