(Methylamino)(4-phenylpiperazinyl)methane-1-thione | 433313-85-0

• 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: (Methylamino)(4-phenylpiperazinyl)methane-1-thione
• 英文别名: N-methyl-4-phenylpiperazine-1-carbothioamide
• CAS: 433313-85-0
• 化学式: C₁₂H₁₇N₃S
• mdl: MFCD02662282
• 分子量: 235.353
• InChiKey: CVINAXLGYOOLNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  50.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Methylamino)(4-phenylpiperazinyl)methane-1-thione 反应 32.5h， 生成 1-(4-methyl-5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl)-4-phenylpiperazine
  参考文献：
  名称：

  轻松地一锅平行合成3-氨基-1,2,4-三唑

  摘要：

  1,2,4-三唑基序存在于许多商业化和研究性生物活性分子中。尽管它对于药物化学很重要，但缺乏针对该分子核心的便捷组合方法。在这里，我们提出一种合成策略，适合在一锅设置中快速制备结构多样的1,2,4-三唑库。关键步骤包括形成硫脲，然后使用1,3-丙烷磺酸内酯进行S-烷基化和连续闭环，从而得到所需的1,2,4-三唑。平行合成可从市售化学品中以节省成本和时间的方式产生数千个1,2,4-三唑。

  DOI：

  10.1021/acscombsci.8b00060
• 作为产物：
  描述：

  N-苯基哌嗪 、 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 (Methylamino)(4-phenylpiperazinyl)methane-1-thione
  参考文献：
  名称：

  轻松地一锅平行合成3-氨基-1,2,4-三唑

  摘要：

  1,2,4-三唑基序存在于许多商业化和研究性生物活性分子中。尽管它对于药物化学很重要，但缺乏针对该分子核心的便捷组合方法。在这里，我们提出一种合成策略，适合在一锅设置中快速制备结构多样的1,2,4-三唑库。关键步骤包括形成硫脲，然后使用1,3-丙烷磺酸内酯进行S-烷基化和连续闭环，从而得到所需的1,2,4-三唑。平行合成可从市售化学品中以节省成本和时间的方式产生数千个1,2,4-三唑。

  DOI：

  10.1021/acscombsci.8b00060

文献信息

• Synthesis of N-substituted-N-acylthioureas of 4-substituted piperazines endowed with local anaesthetic, antihyperlipidemic, antiproliferative activities and antiarrythmic, analgesic, antiaggregating actions
  作者：Angelo Ranise、Andrea Spallarossa、Olga Bruno、Silvia Schenone、Paola Fossa、Giulia Menozzi、Francesco Bondavalli、Luisa Mosti、Annalisa Capuano、Filomena Mazzeo、Giuseppe Falcone、Walter Filippelli

  DOI：10.1016/s0014-827x(03)00132-0

  日期：2003.9

  Three series of N-acyl and N-cyclohexyl- or N-methyl or N-phenyl-thioureas of 4-substituted (methyl, phenyl, 2-pyridyl)piperazines (4-12) were synthesised according to a highly convergent one-pot procedure and tested in vivo (local anaesthetic, anti-hyperlipoproteinemic, analgesic, anti-inflammatory, antiarrythmic activities) and in vitro (antiaggregating and, for some selected derivatives, antiproliferative activities) experiments. All the test compounds showed local anaesthesia in particular 4Ar(4), 5Ar(4), 12Ar(3) (after 5 min) and 5Ar(2), 5Ar(3), 9Ar(4) (after 30 min) were equipotent to lidocaine. In lowering triglyceride levels, compounds 6Ar(4) and 7Ar(3) were more active than nicotinic acid, whereas 7Ar(4) and 11Ar(4) were approximately equipotent. As concerns analgesic activity, 5Ar(2) and 5Ar(4) were as active as indomethacin. Appreciable anti-inflammatory activity was found in 8Ar(1), 5Ar(2) and 11Ar(2), but inferior to that of indomethacin. High levels of antiarrythmic activity, comparable with that of quinidine, were found in derivatives 4Ar(2) and 10Ar(1). Compounds 4Ar(2) and 8Ar(2), assayed in antitumor in vitro screening system at National Cancer Institute (NCI), showed significant antiproliferative activity against ACHN cell line (GI50: 0.13 microM) and NCI-H226 cell line (GI50: 1.03 microM), respectively.
• Facile One-Pot Parallel Synthesis of 3-Amino-1,2,4-triazoles
  作者：Andrey V. Bogolyubsky、Olena Savych、Anton V. Zhemera、Sergey E. Pipko、Alexander V. Grishchenko、Anzhelika I. Konovets、Roman O. Doroshchuk、Dmytro N. Khomenko、Volodymyr S. Brovarets、Yurii S. Moroz、Mykhailo Vybornyi

  DOI：10.1021/acscombsci.8b00060

  日期：2018.7.9

  strategy suitable for the quick preparation of a library of structurally diverse 1,2,4-triazoles in a one-pot setting. The key steps include the formation of thioureas followed by S-alkylation using 1,3-propane sultone and consecutive ring closure leading to the desired 1,2,4-triazoles. Parallel synthesis yields thousands of 1,2,4-triazoles in a cost- and time-efficient manner from commercially available

  1,2,4-三唑基序存在于许多商业化和研究性生物活性分子中。尽管它对于药物化学很重要，但缺乏针对该分子核心的便捷组合方法。在这里，我们提出一种合成策略，适合在一锅设置中快速制备结构多样的1,2,4-三唑库。关键步骤包括形成硫脲，然后使用1,3-丙烷磺酸内酯进行S-烷基化和连续闭环，从而得到所需的1,2,4-三唑。平行合成可从市售化学品中以节省成本和时间的方式产生数千个1,2,4-三唑。