5-([(2-chloroquinolin-3-yl)methyl]sulfanyl)-N-(4-nitrobenzyl)-1,3,4-thiadiazol-2-amine | 1355162-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-([(2-chloroquinolin-3-yl)methyl]sulfanyl)-N-(4-nitrobenzyl)-1,3,4-thiadiazol-2-amine
• 英文别名: 5-[(2-chloroquinolin-3-yl)methylsulfanyl]-N-[(4-nitrophenyl)methyl]-1,3,4-thiadiazol-2-amine
• CAS: 1355162-41-2
• 化学式: C₁₉H₁₄ClN₅O₂S₂
• 分子量: 443.937
• InChiKey: FDSLHMXXOARSHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-氯-3-氯甲基喹啉 在 sodium tetrahydroborate 、 溶剂黄146 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 5-([(2-chloroquinolin-3-yl)methyl]sulfanyl)-N-(4-nitrobenzyl)-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  Design, Synthesis and Screening of Quinoline-Incorporated Thiadiazole as a Potential Anticonvulsant

  摘要：

  A series of quinoline‐incorporated substituted thiadiazole were designed and synthesized using appropriate synthetic route keeping in view the structural requirement of pharmacophore and evaluated for anticonvulsant and CNS activities. After intraperitoneal injection to mice, some synthesized derivatives were examined in the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazol (scPTZ)‐induced seizure and neurotoxicity screens. Those found potent were also evaluated for behavioural impairment and depression activity. Among the compounds tested, 6d and 6e showed protection from seizures in both the animal models at dose level of 30 mg/kg while 7f showed protection against both models at 100 mg/kg dose level. These compounds exhibited lesser CNS depression and neurotoxicity compared with clinically effective drug.

  DOI：

  10.1111/j.1747-0285.2011.01255.x

文献信息

• Design, Synthesis and Screening of Quinoline-Incorporated Thiadiazole as a Potential Anticonvulsant
  作者：Suresh Kumar、Darpan Kaushik、Sandhya Bawa、Suroor A. Khan

  DOI：10.1111/j.1747-0285.2011.01255.x

  日期：2012.1

  A series of quinoline‐incorporated substituted thiadiazole were designed and synthesized using appropriate synthetic route keeping in view the structural requirement of pharmacophore and evaluated for anticonvulsant and CNS activities. After intraperitoneal injection to mice, some synthesized derivatives were examined in the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazol (scPTZ)‐induced seizure and neurotoxicity screens. Those found potent were also evaluated for behavioural impairment and depression activity. Among the compounds tested, 6d and 6e showed protection from seizures in both the animal models at dose level of 30 mg/kg while 7f showed protection against both models at 100 mg/kg dose level. These compounds exhibited lesser CNS depression and neurotoxicity compared with clinically effective drug.