(1-methyl-4-phenyl-1H-imidazol-2-yl)methanamine | 1404113-47-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1-methyl-4-phenyl-1H-imidazol-2-yl)methanamine
• 英文别名: (1-Methyl-4-phenylimidazol-2-yl)methanamine；(1-methyl-4-phenylimidazol-2-yl)methanamine
• CAS: 1404113-47-8
• 化学式: C₁₁H₁₃N₃
• 分子量: 187.244
• InChiKey: ACJGTTDKXBKEFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1-methyl-4-phenyl-1H-imidazol-2-yl)methanamine 在 苯酚 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 7-chloro-N-[[1-methyl-4-phenyl-5-(pyrrolidin-1-ylmethyl)imidazol-2-yl]methyl]quinolin-4-amine
  参考文献：
  名称：

  Synthesis and antiplasmodial activity of new heteroaryl derivatives of 7-chloro-4-aminoquinoline

  摘要：

  With the aim to investigate the effect of different heterocyclic rings linked to the 4-aminoquinoline nucleus on the antimalarial activity, a set of 7-chloro-N-(heteroaryl)-methyl-4-aminoquinoline and 7-chloro-N-(heteroaryl)-4-aminoquinoline was synthesized and tested in vitro against D-10 (CQ-S) and W-2 (CQ-R) strains of Plasmodium falciparum. All compounds exhibited from moderate to high antiplasmodial activities. The activity was strongly influenced both by the presence of a methylenic group, as a spacer between the 4-aminoquinoline and the heterocyclic ring, and by the presence of a basic head. The most potent molecules inhibited the growth of both CQ-S and CQ-R strains of P. falciparum with IC50 < 30 nM and were not toxic against human endothelial cells. These results confirm that the presence of an heteroaryl moiety in the side chain of 7-chloro-4-aminoquinoline is useful for the design and development of new powerful antimalarial agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.040
• 作为产物：
  描述：

  tert-butoxycarbonyl (1-methyl-4-phenyl-1H-imidazol-2-yl)methylamine 在 三氟乙酸 作用下， 反应 0.75h， 以88%的产率得到(1-methyl-4-phenyl-1H-imidazol-2-yl)methanamine
  参考文献：
  名称：

  Synthesis and antiplasmodial activity of new heteroaryl derivatives of 7-chloro-4-aminoquinoline

  摘要：

  With the aim to investigate the effect of different heterocyclic rings linked to the 4-aminoquinoline nucleus on the antimalarial activity, a set of 7-chloro-N-(heteroaryl)-methyl-4-aminoquinoline and 7-chloro-N-(heteroaryl)-4-aminoquinoline was synthesized and tested in vitro against D-10 (CQ-S) and W-2 (CQ-R) strains of Plasmodium falciparum. All compounds exhibited from moderate to high antiplasmodial activities. The activity was strongly influenced both by the presence of a methylenic group, as a spacer between the 4-aminoquinoline and the heterocyclic ring, and by the presence of a basic head. The most potent molecules inhibited the growth of both CQ-S and CQ-R strains of P. falciparum with IC50 < 30 nM and were not toxic against human endothelial cells. These results confirm that the presence of an heteroaryl moiety in the side chain of 7-chloro-4-aminoquinoline is useful for the design and development of new powerful antimalarial agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.040

文献信息

• [EN] NOVEL NITROGENATED HETEROCYCLIC RING DERIVATIVE<br/>[FR] NOUVEAU DÉRIVÉ À NOYAU HÉTÉROCYCLIQUE AZOTÉ
  申请人：MOCHIDA PHARM CO LTD

  公开号：WO2013005798A1

  公开（公告）日：2013-01-10

  　有効性に優れたＰＤＥ１０阻害剤、とりわけ、統合失調症などの精神疾患等の予防または治療剤が求められている。本発明は、下記式（I）で表される含窒素複素環化合物またはそれらの製薬学的に許容される塩、またはそれらの溶媒和物、および当該化合物またはそれらの製薬学的に許容される塩、またはそれらの溶媒和物を有効成分として含有することを特徴とする医薬組成物を提供する。当該医薬組成物は、とりわけＰＤＥ１０阻害剤であり、統合失調症などの精神疾患等の予防または治療剤に用いられるものである。
• Synthesis and antiplasmodial activity of new heteroaryl derivatives of 7-chloro-4-aminoquinoline
  作者：Manolo Casagrande、Anna Barteselli、Nicoletta Basilico、Silvia Parapini、Donatella Taramelli、Anna Sparatore

  DOI：10.1016/j.bmc.2012.07.040

  日期：2012.10

  With the aim to investigate the effect of different heterocyclic rings linked to the 4-aminoquinoline nucleus on the antimalarial activity, a set of 7-chloro-N-(heteroaryl)-methyl-4-aminoquinoline and 7-chloro-N-(heteroaryl)-4-aminoquinoline was synthesized and tested in vitro against D-10 (CQ-S) and W-2 (CQ-R) strains of Plasmodium falciparum. All compounds exhibited from moderate to high antiplasmodial activities. The activity was strongly influenced both by the presence of a methylenic group, as a spacer between the 4-aminoquinoline and the heterocyclic ring, and by the presence of a basic head. The most potent molecules inhibited the growth of both CQ-S and CQ-R strains of P. falciparum with IC50 < 30 nM and were not toxic against human endothelial cells. These results confirm that the presence of an heteroaryl moiety in the side chain of 7-chloro-4-aminoquinoline is useful for the design and development of new powerful antimalarial agents. (C) 2012 Elsevier Ltd. All rights reserved.