4-[[(4-chloropyrimidin-2-yl)-propan-2-ylamino]methyl]-N,N-dimethylimidazole-1-sulfonamide | 1394290-66-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[[(4-chloropyrimidin-2-yl)-propan-2-ylamino]methyl]-N,N-dimethylimidazole-1-sulfonamide
• CAS: 1394290-66-4
• 化学式: C₁₃H₁₉ClN₆O₂S
• 分子量: 358.852
• InChiKey: KHBRYOGPAZLIRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  92.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[[(4-chloropyrimidin-2-yl)-propan-2-ylamino]methyl]-N,N-dimethylimidazole-1-sulfonamide 生成 (4-chloro-pyrimidin-2-yl)-(3H-imidazol-4-ylmethyl)-isopropyl-amine
  参考文献：
  名称：

  Optimisation of imidazole compounds as selective TAAR1 agonists: Discovery of RO5073012

  摘要：

  A series of imidazole compounds has been identified which affords potent and selective partial and full agonists of the TAAR1 receptor. Starting from 2-benzyl-imidazoline screening hits, a series of structurally related 2-benzyl- and 4-benzyl-imidazoles was investigated first, but it proved highly challenging to obtain compounds having sufficient selectivity against the adrenergic alpha 2 receptor. This issue could be successfully addressed by modification of the linker region and SAR exploration led to the discovery of highly selective isopropyl-substituted 4-aminomethyl-imidazole compounds. The work culminated in the identification of the selective TAAR1 partial agonist RO5073012 (4-chlorophenyl)-(1H-imidazol-4-ylmethyl)-isopropyl-amine, 24), which has a good pharmacokinetic profile after oral administration in rodents. RO5073012 has been found to be active in a behavioural rat model which is considered indicative for schizophrenia. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.060
• 作为产物：
  描述：

  4-甲酰基-N,N-二甲基-1H-咪唑-1-磺酰胺 在 sodium tetrahydroborate 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 4.0h， 生成 4-[[(4-chloropyrimidin-2-yl)-propan-2-ylamino]methyl]-N,N-dimethylimidazole-1-sulfonamide
  参考文献：
  名称：

  Optimisation of imidazole compounds as selective TAAR1 agonists: Discovery of RO5073012

  摘要：

  A series of imidazole compounds has been identified which affords potent and selective partial and full agonists of the TAAR1 receptor. Starting from 2-benzyl-imidazoline screening hits, a series of structurally related 2-benzyl- and 4-benzyl-imidazoles was investigated first, but it proved highly challenging to obtain compounds having sufficient selectivity against the adrenergic alpha 2 receptor. This issue could be successfully addressed by modification of the linker region and SAR exploration led to the discovery of highly selective isopropyl-substituted 4-aminomethyl-imidazole compounds. The work culminated in the identification of the selective TAAR1 partial agonist RO5073012 (4-chlorophenyl)-(1H-imidazol-4-ylmethyl)-isopropyl-amine, 24), which has a good pharmacokinetic profile after oral administration in rodents. RO5073012 has been found to be active in a behavioural rat model which is considered indicative for schizophrenia. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.060