2-Propylquinoline-4,6-diamine | 538360-53-1

• 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-Propylquinoline-4,6-diamine
• CAS: 538360-53-1
• 化学式: C₁₂H₁₅N₃
• 分子量: 201.271
• InChiKey: UKXIWSVDCCRKDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  64.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenoxymethyl)-benzoyl chloride 、 2-Propylquinoline-4,6-diamine 在 吡啶 作用下， 反应 12.0h， 生成 N-(4-Amino-2-propyl-quinolin-6-yl)-2-(4-chloro-phenoxymethyl)-benzamide
  参考文献：
  名称：

  4-Aminoquinolines:  Novel Nociceptin Antagonists with Analgesic Activity

  摘要：

  Small-molecule nociceptin antagonists were synthesized to examine their therapeutic potential. After a 4-aminoquinoline derivative was found to bind with the human ORL1 receptor, a series of 4-aminoquinolines and related compounds were synthesized and their binding was evaluated. Elucidation of structure-activity relationships eventually led to the optimum compounds. One of the se compounds, N-(4-amino-2-methylquinolin-6-yl) -2-(4-ethylphenoxymethyl)benzamide hydrochloride (11) not only antagonized nociceptin-induced allodynia in mice but also showed analgesic effect in a hot plate test using mice and in a formalin test using rats. Its analgesic effect was not antagonized by the opioid antagonist naloxone. These results indicate that this nociceptin antagonist has the potential to become a novel type of analgesic that differs from mu -opioid agonists.

  DOI：

  10.1021/jm0002073
• 作为产物：
  描述：

  4′-氨基乙酰苯胺 在 盐酸 、 ammonium acetate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 34.17h， 生成 2-Propylquinoline-4,6-diamine
  参考文献：
  名称：

  4-Aminoquinolines:  Novel Nociceptin Antagonists with Analgesic Activity

  摘要：

  Small-molecule nociceptin antagonists were synthesized to examine their therapeutic potential. After a 4-aminoquinoline derivative was found to bind with the human ORL1 receptor, a series of 4-aminoquinolines and related compounds were synthesized and their binding was evaluated. Elucidation of structure-activity relationships eventually led to the optimum compounds. One of the se compounds, N-(4-amino-2-methylquinolin-6-yl) -2-(4-ethylphenoxymethyl)benzamide hydrochloride (11) not only antagonized nociceptin-induced allodynia in mice but also showed analgesic effect in a hot plate test using mice and in a formalin test using rats. Its analgesic effect was not antagonized by the opioid antagonist naloxone. These results indicate that this nociceptin antagonist has the potential to become a novel type of analgesic that differs from mu -opioid agonists.

  DOI：

  10.1021/jm0002073

文献信息

• [EN] 4-AMINOQUINOLINE COMPOUNDS<br/>[FR] COMPOSES 4-AMINOQUINOLEINES
  申请人：MERCK & CO INC

  公开号：WO2003045920A1

  公开（公告）日：2003-06-05

  The present invention is concerned with compounds of the general Formula I : and pharmaceutically acceptable salts thereof, which are useful as melanin concentrating hormone receptor antagonists, particularly MCH-1R antagonists. As such, compounds of the present invention are useful for the treatment or prevention of obesity or eating disorders associated with excessive food intake and complications thereof, osteoarthritis, certain cancers, AIDS wasting, cachexia, frailty (particularly in elderly), mental disorders stress, cognitive disorders, sexual function, reproductive function, kidney function, locomotor disorders, attention deficit disorder (ADD), substance abuse disorders and dyskinesias, Huntington s disease, epilepsy, memory function, and spinal muscular atrophy. Compounds of formula I may therefore be used in the treatment of these conditions, and in the manufacture of a medicament useful in treating these conditions. Pharmaceutical formulations comprising one of the compounds of formula (I) as an active ingredient are disclosed, as are processes for preparing these compounds.

  本发明涉及一般式I的化合物及其药学上可接受的盐，这些化合物可用作黑色素浓集激素受体拮抗剂，尤其是MCH-1R拮抗剂。因此，本发明的化合物可用于治疗或预防与过度进食及其并发症相关的肥胖症或进食障碍、骨关节炎、某些癌症、艾滋病消耗症、消瘦、虚弱（尤其是老年人）、心理障碍、压力、认知障碍、性功能、生殖功能、肾功能、运动障碍、注意力缺陷障碍（ADD）、物质滥用障碍和运动障碍、亨廷顿病、癫痫、记忆功能和脊髓肌萎缩症。因此，I式化合物可用于治疗这些疾病，并用于制造用于治疗这些疾病的药物。本发明披露了包含一种I式化合物作为活性成分的制药配方，以及制备这些化合物的过程。
• 4-Aminoquinoline compounds
  申请人：DeVita J. Robert

  公开号：US20050009815A1

  公开（公告）日：2005-01-13

  The present invention is concerned with compounds of the general Formula I: and pharmaceutically acceptable salts thereof, which are useful as melanin concentrating hormone receptor antagonists, particularly MCH-1R antagonists. As such, compounds of the present invention are useful for the treatment or prevention of obesity or eating disorders associated with excessive food intake and complications thereof, osteoarthritis, certain cancers, AIDS wasting, cachexia, frailty (particularly in elderly), mental disorders stress, cognitive disorders, sexual function, reproductive function, kidney function, locomotor disorders, attention deficit disorder (ADD), substance abuse disorders and dyskinesias, Huntington's disease, epilepsy, memory function, and spinal muscular atrophy. Compounds of formula I may therefore be used in the treatment of these conditions, and in the manufacture of a medicament useful in treating these conditions. Pharmaceutical formulations comprising one of the compounds of formula (I) as an active ingredient are disclosed, as are processes for preparing these compounds.

  本发明涉及一般式I的化合物及其药用可接受的盐，其作为黑色素浓集激素受体拮抗剂，特别是MCH-1R拮抗剂，具有用途。因此，本发明的化合物可用于治疗或预防与过度进食及其并发症相关的肥胖症或进食障碍、骨关节炎、某些癌症、艾滋病消耗综合征、恶病质、虚弱（特别是老年人）、心理障碍、压力、认知障碍、性功能、生殖功能、肾功能、运动障碍、注意力缺陷障碍（ADD）、物质滥用障碍和运动障碍、亨廷顿病、癫痫、记忆功能和脊髓肌萎缩症。因此，式I的化合物可用于治疗这些疾病，并用于制造用于治疗这些疾病的药物。本发明还揭示了包含式（I）的化合物作为活性成分的制药配方，以及制备这些化合物的过程。
• A Method of Treating Cancer
  申请人：Blizzard Timothy A.

  公开号：US20090012061A1

  公开（公告）日：2009-01-08

  The present invention relates to a method of treating cellular proliferative diseases, in particular cancer, which comprises administering a modulator of the activity of the mitotic kinesin KSP, wherein the activity of the KSP modulator is dependent on the presence of microtubules. It is believed that the KSP modulators utilized in the instant method bind to the KSP protein in a previously unreported manner, since the compounds do not bind competitively with respect to either microtubules or ATP, the substrates of KSP. The modulators useful in the instant methods are furthermore not active against the non-microtubule stimulated activity of KSP. Cellular proliferative diseases that may be treated using the method disclosed herein are, for example cancer, hyperplasias, restenosis, cardiac hypertrophy, immune disorders and inflammation.

  本发明涉及一种治疗细胞增殖性疾病，特别是癌症的方法，其包括给予丝裂期动力蛋白KSP活性调节剂，其中KSP活性调节剂的活性取决于微管的存在。据信，本方法中使用的KSP调节剂以一种先前未报道的方式结合到KSP蛋白上，因为这些化合物不与KSP的底物微管或ATP竞争地结合。此外，本方法中有用的调节剂对于KSP的非微管刺激活性也没有活性。可以使用本文所披露的方法治疗的细胞增殖性疾病包括癌症、增生、再狭窄、心肌肥大、免疫失调和炎症等。
• 4-Aminoquinoline melanin-concentrating hormone 1-receptor (MCH1R) antagonists
  作者：Jinlong Jiang、Peter Lin、Myle Hoang、Lehua Chang、Carina Tan、Scott Feighner、Oksana C. Palyha、Donna L. Hreniuk、Jie Pan、Andreas W. Sailer、Nancy R. Morin、Douglas J. MacNeil、Andrew D. Howard、Lex H.T. Van der Ploeg、Mark T. Goulet、Robert J. DeVita

  DOI：10.1016/j.bmcl.2006.08.008

  日期：2006.10

  Structure-activity relationships of a 4-aminoquinoline MCHlR antagonist lead series were explored by synthesis of analogs with modifications at the 2-, 4-, and 6-positions of the original HTS hit. Improvements to the original screening lead included lipophilic groups at the 2-position and biphenyl, cyclohexyl phenyl, and hydrocinnamyl carboxamides at the 6-position. Modifications of the 4-amino group were not well tolerated. (c) 2006 Elsevier Ltd. All rights reserved.
• PROCESS FOR COATING A SURFACE
  申请人：Novartis AG

  公开号：EP1252222B1

  公开（公告）日：2005-11-09