1,2-dihydro-2,2,4-trimethyl-6-methoxyquinoline hydrochloride | 4153-89-3

• 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: 1,2-dihydro-2,2,4-trimethyl-6-methoxyquinoline hydrochloride
• 英文别名: 6-methoxy-2,2,4-trimethyl-1H-quinoline;hydrochloride
• CAS: 4153-89-3
• 化学式: C₁₃H₁₇NO*ClH
• 分子量: 239.745
• InChiKey: FZCGYNYHGIGLFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  21.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-dihydro-2,2,4-trimethyl-6-methoxyquinoline hydrochloride 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 1-(6-Methoxy-4-methylquinazolin-2-yl)-2-methylguanidine
  参考文献：
  名称：

  Quinazolines as adenosine receptor antagonists: SAR and selectivity for A2B receptors

  摘要：

  We have recently reported the discovery of numerous new compounds that are selective inhibitors of all of the subtypes of the adenosine receptor family via a pharmacophore database searching and screening strategy. During the course of this work we made the unexpected discovery of a potent A(2B) receptor antagonist, 4-methyl-7-methoxyquinazolyl-2-(2'-amino-4'-imidazolinone) (38, CMB 6446), which showed selectivity for this receptor and functioned as an antagonist, with a binding K-i value of H 2 nM. We explored the effects of both substituent- and ring-structural variations on the receptor affinity in this series of derivatives, which were found to be mostly non-selective adenosine receptor ligands with K-i values in the micromolar range. Since no enhancement of A(2B) receptor affinity of 38 was achieved, the previously reported pharmacophore-based searching strategy yielded the most potent and selective structurally-related hit in the database originally searched. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00323-1
• 作为产物：
  描述：

  甲氧苯胺 、 丙酮 在 对叔丁基邻苯二酚 、 碘 、 magnesium sulfate 、 盐酸 作用下， 以 乙醚 为溶剂， 反应 17.5h， 以40%的产率得到1,2-dihydro-2,2,4-trimethyl-6-methoxyquinoline hydrochloride
  参考文献：
  名称：

  [EN] BIS-QUINAZOLINE COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS
  [FR] COMPOSES DE BIS-QUINAZOLINE POUR LE TRAITEMENT DES INFECTIONS BACTERIENNES

  摘要：

  公开号：

  WO2005030131A3

文献信息

• [EN] BIS-QUINAZOLINE COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS<br/>[FR] COMPOSES DE BIS-QUINAZOLINE POUR LE TRAITEMENT DES INFECTIONS BACTERIENNES
  申请人：REPLIDYNE INC

  公开号：WO2005030131A3

  公开（公告）日：2005-05-12
• Quinazolines as adenosine receptor antagonists: SAR and selectivity for A2B receptors
  作者：Thomas R Webb、Dmitriy Lvovskiy、Soon-Ai Kim、Xiao-duo Ji、Neli Melman、Joel Linden、Kenneth A Jacobson

  DOI：10.1016/s0968-0896(02)00323-1

  日期：2003.1

  We have recently reported the discovery of numerous new compounds that are selective inhibitors of all of the subtypes of the adenosine receptor family via a pharmacophore database searching and screening strategy. During the course of this work we made the unexpected discovery of a potent A(2B) receptor antagonist, 4-methyl-7-methoxyquinazolyl-2-(2'-amino-4'-imidazolinone) (38, CMB 6446), which showed selectivity for this receptor and functioned as an antagonist, with a binding K-i value of H 2 nM. We explored the effects of both substituent- and ring-structural variations on the receptor affinity in this series of derivatives, which were found to be mostly non-selective adenosine receptor ligands with K-i values in the micromolar range. Since no enhancement of A(2B) receptor affinity of 38 was achieved, the previously reported pharmacophore-based searching strategy yielded the most potent and selective structurally-related hit in the database originally searched. (C) 2002 Elsevier Science Ltd. All rights reserved.