3-((2-(1H-indol-3-yl)ethyl)carbamoyl)-1-benzylpyridin-1-ium bromide | 89651-77-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-((2-(1H-indol-3-yl)ethyl)carbamoyl)-1-benzylpyridin-1-ium bromide
• 英文别名: 1-benzyl-N-[2-(1H-indol-3-yl)ethyl]pyridin-1-ium-3-carboxamide;bromide
• CAS: 89651-77-4
• 化学式: Br*C₂₃H₂₂N₃O
• 分子量: 436.351
• InChiKey: BQUDOMQSUTVRDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.48
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  48.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-((2-(1H-indol-3-yl)ethyl)carbamoyl)-1-benzylpyridin-1-ium bromide 在 sodium ethanolate 、 镍 作用下， 以 四氢呋喃 、 乙醇 、 xylene 为溶剂， 反应 2.67h， 生成 7-苄基-2-[2-(1H-吲哚-3-基)乙基]-2,7-萘啶-1,3(2H,7H)-二酮
  参考文献：
  名称：

  Inter- and intramolecular addition of ester anions to nicotinium salts

  摘要：

  DOI：

  10.1016/s0040-4020(01)88606-3
• 作为产物：
  描述：

  烟酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 3-((2-(1H-indol-3-yl)ethyl)carbamoyl)-1-benzylpyridin-1-ium bromide
  参考文献：
  名称：

  New multifunctional melatonin-derived benzylpyridinium bromides with potent cholinergic, antioxidant, and neuroprotective properties as innovative drugs for Alzheimer's disease

  摘要：

  A novel series of melatonin-derived benzylpyridinium bromides have been designed, synthesized, and evaluated as multi-functional anti-AD agents with cholinesterase inhibitory, antioxidant, and neuroprotective activities. In vitro studies showed that most of these compounds exhibited potent inhibitory activity toward h-AChE and h-BuChE, and good antioxidant capacity in the ORAC assay. In particular, compound 19 was the most attractive derivative, showing the highest potency to inhibit ChEs (AChE: IC50 = 0.11 mu M; BuChE: IC50 = 1.1 mu M) and good antioxidant ability (ORAC (trolox) = 3.41). Kinetic and molecular modeling studies indicated that 19 was a mixed-type inhibitor, binding simultaneously to active and peripheral sites of AChE. Moreover, 19 also showed good neuroprotective effects in human SH-SY5Y neuroblastoma cells. Taken together, these results suggested that compound 19 might be a promising multi-target drug candidate worthy of further pursuit. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.08.052

文献信息

• Inter- and intramolecular addition of ester anions to nicotinium salts
  作者：Martin J. Wanner、Gerrit Jan Koomen、Upendra K. Pandit

  DOI：10.1016/s0040-4020(01)88606-3

  日期：1983.1
• New multifunctional melatonin-derived benzylpyridinium bromides with potent cholinergic, antioxidant, and neuroprotective properties as innovative drugs for Alzheimer's disease
  作者：Xiao-Ting Luo、Chun-Ming Wang、Yun Liu、Zhen-Guang Huang

  DOI：10.1016/j.ejmech.2015.08.052

  日期：2015.10

  A novel series of melatonin-derived benzylpyridinium bromides have been designed, synthesized, and evaluated as multi-functional anti-AD agents with cholinesterase inhibitory, antioxidant, and neuroprotective activities. In vitro studies showed that most of these compounds exhibited potent inhibitory activity toward h-AChE and h-BuChE, and good antioxidant capacity in the ORAC assay. In particular, compound 19 was the most attractive derivative, showing the highest potency to inhibit ChEs (AChE: IC50 = 0.11 mu M; BuChE: IC50 = 1.1 mu M) and good antioxidant ability (ORAC (trolox) = 3.41). Kinetic and molecular modeling studies indicated that 19 was a mixed-type inhibitor, binding simultaneously to active and peripheral sites of AChE. Moreover, 19 also showed good neuroprotective effects in human SH-SY5Y neuroblastoma cells. Taken together, these results suggested that compound 19 might be a promising multi-target drug candidate worthy of further pursuit. (C) 2015 Elsevier Masson SAS. All rights reserved.