2-nitro-5,6-dihydro-6-acetyldibenzo[b,f][1,4,5]thiadiazepine | 1615684-16-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-nitro-5,6-dihydro-6-acetyldibenzo[b,f][1,4,5]thiadiazepine
• 英文别名: 1-(2-nitro-5H-benzo[c][5,1,2]benzothiadiazepin-6-yl)ethanone
• CAS: 1615684-16-6
• 化学式: C₁₄H₁₁N₃O₃S
• 分子量: 301.326
• InChiKey: VFIREGNJWDIGNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  {2-[(2,4-dinitrophenyl)thio]phenyl}hydrazine 在 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.25h， 生成 2-nitro-5,6-dihydro-6-acetyldibenzo[b,f][1,4,5]thiadiazepine
  参考文献：
  名称：

  Dibenzo[1,4,5]thiadiazepine: A hardly-known heterocyclic system with neuroprotective properties of potential usefulness in the treatment of neurodegenerative diseases

  摘要：

  In this work we describe a new family of dibenzo[1,4,5]thiadiazepines (2-12) that showed an interesting in vitro biological profile, namely neuroprotective and antioxidant properties, as well as blockade of cytosolic calcium entry. They showed no cytotoxic effects and the majority were predicted as CNS-permeable compounds. In human neuroblastoma cells they displayed good neuroprotective properties against mitochondrial oxidative stress which, in many cases, almost reached the full protection (>90%) when compounds were incubated with cells 24 h before the addition of toxic stressors. In co-incubation conditions these figures were smaller, although some compounds maintained an interesting level of neuroprotection, higher than 50%. Four selected compounds (2, 5, 8, and 11) were found to be effective antioxidant agents by sequestering mitochondrial radical oxygen species (ROS). Moreover, compound 2 showed a remarkable calcium-channel modulating activity. The interest of these compounds is increased by the fact that dibenzo[1,4,5]thiadiazepine is a barely known structure that is not difficult to synthesize and presents very few described derivatives, opening a new and broad line of research in Medicinal Chemistry. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.075

文献信息

• Dibenzo[1,4,5]thiadiazepine: A hardly-known heterocyclic system with neuroprotective properties of potential usefulness in the treatment of neurodegenerative diseases
  作者：Gema C. González-Muñoz、Mariana P. Arce、Concepción Pérez、Alejandro Romero、Mercedes Villarroya、Manuela G. López、Santiago Conde、María Isabel Rodríguez-Franco

  DOI：10.1016/j.ejmech.2014.04.075

  日期：2014.6

  In this work we describe a new family of dibenzo[1,4,5]thiadiazepines (2-12) that showed an interesting in vitro biological profile, namely neuroprotective and antioxidant properties, as well as blockade of cytosolic calcium entry. They showed no cytotoxic effects and the majority were predicted as CNS-permeable compounds. In human neuroblastoma cells they displayed good neuroprotective properties against mitochondrial oxidative stress which, in many cases, almost reached the full protection (>90%) when compounds were incubated with cells 24 h before the addition of toxic stressors. In co-incubation conditions these figures were smaller, although some compounds maintained an interesting level of neuroprotection, higher than 50%. Four selected compounds (2, 5, 8, and 11) were found to be effective antioxidant agents by sequestering mitochondrial radical oxygen species (ROS). Moreover, compound 2 showed a remarkable calcium-channel modulating activity. The interest of these compounds is increased by the fact that dibenzo[1,4,5]thiadiazepine is a barely known structure that is not difficult to synthesize and presents very few described derivatives, opening a new and broad line of research in Medicinal Chemistry. (C) 2014 Elsevier Masson SAS. All rights reserved.