3-[(4-phenylpiperazin-1-yl)methyl]-5-(quinolin-2-yl)-1,3,4-oxadiazol-2(3H)-thione | 1383551-03-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-[(4-phenylpiperazin-1-yl)methyl]-5-(quinolin-2-yl)-1,3,4-oxadiazol-2(3H)-thione
• 英文别名: 3-[(4-Phenylpiperazin-1-yl)methyl]-5-quinolin-2-yl-1,3,4-oxadiazole-2-thione；3-[(4-phenylpiperazin-1-yl)methyl]-5-quinolin-2-yl-1,3,4-oxadiazole-2-thione
• CAS: 1383551-03-8
• 化学式: C₂₂H₂₁N₅OS
• 分子量: 403.508
• InChiKey: XHFQCFJXCOQQNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  76.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  喹啉-2-甲酰肼 在 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 9.0h， 生成 3-[(4-phenylpiperazin-1-yl)methyl]-5-(quinolin-2-yl)-1,3,4-oxadiazol-2(3H)-thione
  参考文献：
  名称：

  Preparation and antimicrobial activity evaluation of some quinoline derivatives containing an azole nucleus

  摘要：

  由喹哪啶酸(1)获得的喹啉-2-碳酰肼(2)通过用异(硫代)氰酸苄酯处理转化为相应的硫代甲酰胺3和甲酰胺6。 3和6的碱性处理得到相应的1,2,4-三唑衍生物4和7。5-(喹啉-2-基)-1,3,4-恶二唑-2-硫醇(9)的合成为由1与CS_2在基本介质中的反应进行。 化合物4、7和9的曼尼希反应导致形成氨烷基化衍生物5a-c、8和10a、b。 1与氨基硫脲、碳酰肼或硫代碳酰肼缩合得到相应的1,2,4-三唑衍生物(11-13)。 用4-氯苯甲酰溴处理4-氨基-5-(喹啉-2-基)-4H-1,2,4-三唑-3-硫醇(13)导致形成稠合三唑并噻二嗪14。13的缩合与4-甲氧基苯甲醛反应生成相应的席夫碱15。新合成的化合物通过元素分析、IR、^1H-NMR、^{13}C-NMR和质谱进行表征。抗菌活性研究表明，一些新合成的化合物对多种微生物表现出良好至中等的活性。

  DOI：

  10.3906/kim-1109-9

文献信息

• Synthesis, molecular modeling and biological evaluation of 2-aminomethyl-5-(quinolin-2-yl)-1,3,4-oxadiazole-2(3H)-thione quinolone derivatives as novel anticancer agent
  作者：Juan Sun、Hui Zhu、Zhong-Ming Yang、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2012.11.039

  日期：2013.2

  A series of quinoline derivatives (4a-4o) have been synthesized and their biological activities were also evaluated as potential telomerase inhibitors. Bioassay tests demonstrated that most of the compounds exhibited substantial broad-spectrum antitumor activity against the three cancer cell lines (HepG2, SGC-7901 and MCF-7). Moreover, all the title compounds were assayed for telomerase inhibition using the TRAP-PCR-ELISA assay. Compounds 4d and 4i displayed the most potent anticancer activities, which were comparable to the positive control. Docking simulation was performed to position compounds 4d and 4i into the telomerase structure active site to determine the probable binding model. Compounds 4d and 4i with potent inhibitory activity in tumor growth inhibition may be potential anticancer agents. (C) 2012 Elsevier Masson SAS. All rights reserved.