N2-[cis-4-(aminomethyl)cyclohexyl]-N4,N4-dimethylquinazoline-2,4-diamine | 509142-63-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N2-[cis-4-(aminomethyl)cyclohexyl]-N4,N4-dimethylquinazoline-2,4-diamine
• 英文别名: N²-[cis-4-(aminomethyl)cyclohexyl]-N⁴,N⁴-dimethylquinazoline-2,4-diamine
• CAS: 509142-63-6
• 化学式: C₁₇H₂₅N₅
• 分子量: 299.419
• InChiKey: HHSGHPCBSYNFLX-BETUJISGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  67.07
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N2-[cis-4-(aminomethyl)cyclohexyl]-N4,N4-dimethylquinazoline-2,4-diamine 在 硼烷四氢呋喃络合物 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 N⁴,N⁴-dimethyl-N²-{cis-4-[({2-[2-(trifluoromethoxy)phenyl]ethyl}amino)methyl]cyclohexyl}quinazoline-2,4-diamine dihydrochloride
  参考文献：
  名称：

  Identification of 4-amino-2-cyclohexylaminoquinazolines as metabolically stable melanin-concentrating hormone receptor 1 antagonists

  摘要：

  The optimization of the distance between two key pharmacophore features within our first hit compounds la and 2a led to the identification of a new class of potent non-peptidic antagonists for the MCH-R1, based around 4-amino-2-cyclohexylamino-quinazolines. In particular, ATC0065 (2c), N-2-[cis-4-({2-[4-Bromo-2-(trifluoromethoxy)phenyl]ethyl}amino)cyclohexyl]-N-4,N-4-dimethylquinazoline-2,4-diamine dihydrochloride, bound with high affinity to the MCH-R1 (IC50 value of 16 nM) and showed good metabolic stability in liver microsomes from human and rat. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.052
• 作为产物：
  描述：

  2,4-二氯喹唑啉 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 、 异丙醇 为溶剂， 反应 229.33h， 生成 N2-[cis-4-(aminomethyl)cyclohexyl]-N4,N4-dimethylquinazoline-2,4-diamine
  参考文献：
  名称：

  Identification of 4-amino-2-cyclohexylaminoquinazolines as metabolically stable melanin-concentrating hormone receptor 1 antagonists

  摘要：

  The optimization of the distance between two key pharmacophore features within our first hit compounds la and 2a led to the identification of a new class of potent non-peptidic antagonists for the MCH-R1, based around 4-amino-2-cyclohexylamino-quinazolines. In particular, ATC0065 (2c), N-2-[cis-4-({2-[4-Bromo-2-(trifluoromethoxy)phenyl]ethyl}amino)cyclohexyl]-N-4,N-4-dimethylquinazoline-2,4-diamine dihydrochloride, bound with high affinity to the MCH-R1 (IC50 value of 16 nM) and showed good metabolic stability in liver microsomes from human and rat. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.052

文献信息

• Novel quinazoline derivatives and methods of treatment related to the use thereof
  申请人：Sekiguchi Yoshinori

  公开号：US20070010671A1

  公开（公告）日：2007-01-11

  The present invention relates to novel compounds of Formula (1): which act as MCH receptor antagonists. These compositions are useful in pharmaceutical compositions whose use includes prophylaxis or treatment of improving memory function, sleeping and arousal, anxiety, depression, mood disorders, seizure, obesity, diabetes, appetite and eating disorders, cardiovascular disease, hypertension, dyslipidemia, myocardial infarction, binge eating disorders including bulimia, anorexia, mental disorders including manic depression, schizophrenia, delirium, dementia, stress, cognitive disorders, attention deficit disorder, substance abuse disorders and dyskinesias including Parkinson's disease, epilepsy, and addiction.

  本发明涉及一种新的化合物，其化学式为(1)，并作为MCH受体拮抗剂。这些化合物在制药组合物中的使用包括预防或治疗改善记忆功能、睡眠和觉醒、焦虑、抑郁、情绪障碍、癫痫、肥胖症、糖尿病、食欲和进食障碍、心血管疾病、高血压、血脂异常、心肌梗塞、暴食障碍（包括贪食症、厌食症）、精神障碍（包括躁郁症、精神分裂症、谵妄、痴呆）、压力、认知障碍、注意力缺陷障碍、物质滥用障碍和运动障碍（包括帕金森病、癫痫和成瘾）。
• Mch receptor antagonists
  申请人：Sekiguchi Yoshinori

  公开号：US20070037836A1

  公开（公告）日：2007-02-15

  The present invention relates to novel compounds of the formula (I) which act as MCH receptor antagonists. These compositions are useful in pharmaceutical compositions whose use includes prophylaxis or treatment of obesity, obesity related disorders, anxiety, or depression.

  本发明涉及具有式(I)的新型化合物，其作为MCH受体拮抗剂。这些组合物在药物组合物中有用，其使用包括预防或治疗肥胖症、与肥胖相关的疾病、焦虑或抑郁症。
• MCH receptor antagonists
  申请人：Taisho Pharmaceutical Co., Ltd.

  公开号：US07544690B2

  公开（公告）日：2009-06-09

  The present invention relates to novel compounds of the formula (I) which act as MCH receptor antagonists. These compositions are useful in pharmaceutical compositions whose use includes prophylaxis or treatment of obesity, obesity related disorders, anxiety, or depression.

  本发明涉及一种新型化合物，其化学式为（I），可作为MCH受体拮抗剂。这些化合物可用于制备药物组合物，用于预防或治疗肥胖、肥胖相关疾病、焦虑或抑郁症。
• US7544690B2
  申请人：——

  公开号：US7544690B2

  公开（公告）日：2009-06-09