4-(3-(1H-pyrrole-3-carboxamido)phenyl)-2-amino-1H-imidazol-3-ium chloride | 1574306-36-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(3-(1H-pyrrole-3-carboxamido)phenyl)-2-amino-1H-imidazol-3-ium chloride
• 英文别名: N-[3-(2-amino-1H-imidazol-3-ium-5-yl)phenyl]-1H-pyrrole-3-carboxamide;chloride
• CAS: 1574306-36-7
• 化学式: C₁₄H₁₃N₅O*ClH
• 分子量: 303.751
• InChiKey: BYMJENRQVXDKHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  5
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴-3'-硝基苯乙酮 在 N-甲基吗啉 、 盐酸 、 4-二甲氨基吡啶 、 palladium on activated charcoal 、 氢气 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙醇-D1 、 乙腈 为溶剂， 反应 43.17h， 生成 4-(3-(1H-pyrrole-3-carboxamido)phenyl)-2-amino-1H-imidazol-3-ium chloride
  参考文献：
  名称：

  Substituted 4-phenyl-2-aminoimidazoles and 4-phenyl-4,5-dihydro-2-aminoimidazoles as voltage-gated sodium channel modulators

  摘要：

  Voltage-gated sodium channels play an integral part in neurotransmission and their dysfunction is frequently a cause of various neurological disorders. On the basis of the structure of marine alkaloid clathrodin, twenty eight new analogs were designed, synthesized and tested for their ability to block human Na(v)1.3, Na(v)1.4 and Na(v)1.7 channels, as well as for their selectivity against human cardiac isoform Na(v)1.5, using automated patch clamp electrophysiological assay. Several compounds exhibited promising activities on different Na-v channel isoforms in the medium micromolar range and some of the compounds showed also moderate isoform selectivities. The most promising results were obtained for the Na(v)1.3 channel, for which four compounds were found to possess IC50 values lower than 15 mu M. All of the active compounds bind to the open-inactivated states of the channels and therefore act as state-dependent modulators. The obtained results validate the approach of using natural products driven chemistry for drug discovery starting points and represent a good foundation for future design of selective Na-v modulators. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.034