2-氨基-6-氯-3,4-二氢喹唑啉 | 1005550-46-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 2-氨基-6-氯-3,4-二氢喹唑啉
• 英文名称: 2-amino-6-chloro-3,4-dihydroquinazoline
• 英文别名: 6-chloro-1,4-dihydroquinazolin-2-amine
• CAS: 1005550-46-8
• 化学式: C₈H₈ClN₃
• 分子量: 181.625
• InChiKey: XXJMPUMRHCNWPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-氨基-6-氯-3,4-二氢喹唑啉 在 盐酸 作用下， 以 乙醇 为溶剂， 以54%的产率得到2-amino-6-chloro-3,4-dihydroquinazoline hydrochloride
  参考文献：
  名称：

  2-Amino-6-chloro-3,4-dihydroquinazoline: A novel 5-HT3 receptor antagonist with antidepressant character

  摘要：

  2-Amino-6-chloro-3,4-dihydroquinazoline HCl (A6CDQ, 4) binds at 5-HT3 serotonin receptors and displays antidepressant-like action in the mouse tail suspension test (TST). Empirically, 4 was demonstrated to be a 5-HT3 receptor antagonist (two-electrode voltage clamp recordings using frog oocytes; IC50 = 0.26 mu M), and one that should readily penetrate the blood-brain barrier (log P = 1.86). 5-HT3 receptor antagonists represent a potential approach to the development of new antidepressants, and 4 is an example of a structurally novel 5-HT3 receptor antagonist that is active in a preclinical antidepressant model (i.e., the mouse TST). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.072
• 作为产物：
  描述：

  5-氯靛红酸酐 在 硼烷四氢呋喃络合物 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 8.5h， 生成 2-氨基-6-氯-3,4-二氢喹唑啉
  参考文献：
  名称：

  2-Amino-6-chloro-3,4-dihydroquinazoline: A novel 5-HT3 receptor antagonist with antidepressant character

  摘要：

  2-Amino-6-chloro-3,4-dihydroquinazoline HCl (A6CDQ, 4) binds at 5-HT3 serotonin receptors and displays antidepressant-like action in the mouse tail suspension test (TST). Empirically, 4 was demonstrated to be a 5-HT3 receptor antagonist (two-electrode voltage clamp recordings using frog oocytes; IC50 = 0.26 mu M), and one that should readily penetrate the blood-brain barrier (log P = 1.86). 5-HT3 receptor antagonists represent a potential approach to the development of new antidepressants, and 4 is an example of a structurally novel 5-HT3 receptor antagonist that is active in a preclinical antidepressant model (i.e., the mouse TST). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.072

文献信息

• Cyclic guanidines as dual 5-HT5A/5-HT7 receptor ligands: Structure–activity relationship elucidation
  作者：Jens-Uwe Peters、Thomas Lübbers、Alexander Alanine、Sabine Kolczewski、Francesca Blasco、Lucinda Steward

  DOI：10.1016/j.bmcl.2007.10.080

  日期：2008.1

  The optimisation of affinity and selectivity in a novel series of dual 5-HT5A/5-HT7 receptor ligands is described. Brain penetrant 2-aminodihydroquinazolines with low nanomolar affinities were identified. (C) 2007 Elsevier Ltd. All rights reserved.
• 2-Amino-6-chloro-3,4-dihydroquinazoline: A novel 5-HT3 receptor antagonist with antidepressant character
  作者：Małgorzata Dukat、Katie Alix、Jessica Worsham、Shailesh Khatri、Marvin K. Schulte

  DOI：10.1016/j.bmcl.2013.08.072

  日期：2013.11

  2-Amino-6-chloro-3,4-dihydroquinazoline HCl (A6CDQ, 4) binds at 5-HT3 serotonin receptors and displays antidepressant-like action in the mouse tail suspension test (TST). Empirically, 4 was demonstrated to be a 5-HT3 receptor antagonist (two-electrode voltage clamp recordings using frog oocytes; IC50 = 0.26 mu M), and one that should readily penetrate the blood-brain barrier (log P = 1.86). 5-HT3 receptor antagonists represent a potential approach to the development of new antidepressants, and 4 is an example of a structurally novel 5-HT3 receptor antagonist that is active in a preclinical antidepressant model (i.e., the mouse TST). (C) 2013 Elsevier Ltd. All rights reserved.