3-benzyl-5-(3-carboxypropyl)-tetrahydro-2H-1,3,5-thiadiazine-2-thione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪类
• 英文名称: 3-benzyl-5-(3-carboxypropyl)-tetrahydro-2H-1,3,5-thiadiazine-2-thione
• 英文别名: 4-(5-Benzyl-6-thioxo-1,3,5-thiadiazinan-3-yl)butanoic acid；4-(5-benzyl-6-sulfanylidene-1,3,5-thiadiazinan-3-yl)butanoic acid
• 化学式: C₁₄H₁₈N₂O₂S₂
• 分子量: 310.441
• InChiKey: SAFBQMYBOFUELH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 potassium benzylcarbamodithioate 、 4-氨基丁酸 在 phosphate buffer 作用下， 以 水 为溶剂， 反应 2.0h， 生成 3-benzyl-5-(3-carboxypropyl)-tetrahydro-2H-1,3,5-thiadiazine-2-thione
  参考文献：
  名称：

  Synthesis and antimycobacterial activity of 3,5-disubstituted thiadiazine thiones

  摘要：

  A series of 3,5-disubstituted thiadiazine thiones (4-24) have been synthesized by reaction of primary amines with carbon disulphide followed by cyclocondensation of the resulting intermediate with formaldehyde and primary amines or amino acids. The compounds were screened for antitubercular activity in vitro against Mycobacterium tuberculosis H37Rv. Three compounds 4, 12 and 18 showed antimycobacterial activity with MIC 12.5 mug/mL. Compound 4, was tested in vitro against five multidrug resistant (MDR) strains of M. tuberculosis and was found to be active. Compound 4 also exhibited activity in vivo. While all the mice died in the untreated group, the mean survival time (MST) of the compound treated mice was enhanced, 33% mice were surviving in treated group and the load of bacilli in the lung was considerably less in the compound treated group than in the untreated control group. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00480-2

文献信息

• Targeting γ-Aminobutyric Acid (GABA) Carriers to the Brain: Potential Relevance as Antiepileptic Pro-Drugs
  作者：Mohammad Semreen、Abdel-Nasser El-Shorbagi、Taleb Al-Tel、Izzeddin Alsalahat

  DOI：10.2174/1573406411006030144

  日期：2010.5.1

  be an area of intensive investigation in medicinal chemistry. 3,5-Disubstituted tetrahydro-2H-1,3,5-thiadiazine-2-thione (THTT) derivatives, 3a-g, potential prodrugs incorporating the neurotransmitter GABA were synthesized and studied for crossing the blood-brain barrier (BBB). Compounds were prepared from primary amines and carbon disulfide to give dithiocarbamates 2a-g which upon reaction in situ

  寻找具有更高选择性活性的抗癫痫化合物仍然是药物化学领域深入研究的领域。合成了3,5-二取代的四氢-2H-1,3,5-噻二嗪-2-硫酮（THTT）衍生物3a-g，其中掺入了神经递质GABA的潜在前药可用于穿越血脑屏障（BBB）。由伯胺和二硫化碳制备化合物，得到二硫代氨基甲酸酯2a-g，其与甲醛原位反应后提供中间体Ia-g。将Ia-g加到GABA上得到标题化合物3a-g。通过光谱数据验证了结构，并使用HPLC研究了脑中化合物的含量。确定小鼠脑中测试化合物的浓度分布，并测量体内抗惊厥活性。