N-phenyl-4-(pyridin-2-yl)piperazine-1-carbothioamide | 330865-56-0

• 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: N-phenyl-4-(pyridin-2-yl)piperazine-1-carbothioamide
• 英文别名: 4-[2]pyridyl-piperazine-1-carbothioic acid anilide；4-[2]Pyridyl-piperazin-1-thiocarbonsaeure-anilid；N-phenyl-4-pyridin-2-ylpiperazine-1-carbothioamide
• CAS: 330865-56-0
• 化学式: C₁₆H₁₈N₄S
• 分子量: 298.412
• InChiKey: JHUGFIKZRYEKOB-UHFFFAOYSA-N

物化性质

• 熔点：
  140-141 °C
• 沸点：
  465.1±55.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-噻吩甲酰氯 、 N-phenyl-4-(pyridin-2-yl)piperazine-1-carbothioamide 在 吡啶 、 sodium hydride 作用下， 反应 4.0h， 生成 N-phenyl-[(4-pyridin-2-ylpiperazin-1-yl)carbonothioyl]thiophene-2-carboxamide
  参考文献：
  名称：

  Synthesis of N-substituted-N-acylthioureas of 4-substituted piperazines endowed with local anaesthetic, antihyperlipidemic, antiproliferative activities and antiarrythmic, analgesic, antiaggregating actions

  摘要：

  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.

  DOI：

  10.1016/s0014-827x(03)00132-0
• 作为产物：
  描述：

  、 硫代异氰酸苯酯 以 二氯甲烷 为溶剂， 以84%的产率得到N-phenyl-4-(pyridin-2-yl)piperazine-1-carbothioamide
  参考文献：
  名称：

  β-葡萄糖醛酸苷酶抑制剂的不对称杂环硫脲的合成与评价

  摘要：

  合成了硫脲类似物1 – 20，并评估了其体外β-葡萄糖醛酸苷酶抑制潜力。化合物9（0.86±0.01μM），6（1.24±0.01μM），16（1.64±0.02μM）和15（2.12±0.02μM）显示出有效的活性。其他类似物1 - 5，7，8，10，11，13，17，20显示出比标准药物更好的活性d-蔗糖酸1,4-内酯（47.34±0.21μM）范围为4.36–34.4μM。所有合成化合物均通过不同的光谱方法表征。这项研究确定了一种新型的有效抑制剂β-葡萄糖醛酸酶。

  DOI：

  10.1007/s00044-015-1369-x

文献信息

• Fluorous electrophilic scavengers for solution-phase parallel synthesis
  作者：Wei Zhang、Christine Hiu-Tung Chen、Tadamichi Nagashima

  DOI：10.1016/s0040-4039(03)00178-3

  日期：2003.3

  A fluorous isatoic anhydride and isocyanate are synthesized and used as scavengers for amines in solution-phase parallel synthesis of urea, thiourea, and β-hydroxyamine analogs. The resulting fluorous derivatives are readily separated from the reaction mixture by solid-phase extractions (SPE) over FluoroFlash™ cartridges to give products with good purity. The SPE cartridges can be reused.

  在尿素，硫脲和β-羟胺类似物的溶液相平行合成中，合成了氟代等位酸酐和异氰酸酯，并将其用作胺的清除剂。通过在Fluoro Flash ™柱上进行固相萃取（SPE），可以轻松地从反应混合物中分离出所得的氟衍生物，从而获得具有良好纯度的产品。SPE墨盒可以重复使用。
• Design, synthesis, <i>in vitro</i> and <i>in silico</i> bioactivity profiles of new urea/thiourea derivatives of 2-pyridyl piperazine as potent antioxidant and antimicrobial agents: chemo-bio-computational approach
  作者：S. Sumalatha、Ch. Venkataramaiah、C. Naga Raju

  DOI：10.1080/07391102.2022.2072952

  日期：——

  Abstract Synthesis of a series of new urea and thiourea derivatives of 2-pyridyl piperazine was accomplished by reacting various isocyanates and isothiocyanates in the presence of triethylamine (TEA) at 50 °C. All the title compounds were obtained in high yields and their structures were characterized by IR, 1H, 13C NMR, Mass spectral, and Elemental analysis. The synthesized compounds were screened

  摘要 通过在三乙胺 (TEA) 存在下于 50 °C 下使各种异氰酸酯和异硫氰酸酯反应，合成了一系列新型 2-吡啶基哌嗪的脲和硫脲衍生物。所有标题化合物均以高产率获得，其结构通过 IR、1 H、13 C NMR、质谱和元素分析进行​​了表征。对合成的化合物进行了体外和计算机抗氧化和抗菌活性筛选。所有标题化合物均表现出有效的抗氧化和抗菌活性。其中，2c和2f对抗 DPPH，H 2 O 2和氮氧化物表现出显着的活性，活性水平高于参考化合物、抗坏血酸和 BHT。而2a、2c、2f和2j在对所有测试的微生物菌株的抑菌圈方面显示出比标准品（如左氧氟沙星和制霉菌素）显着的活性。此外，计算机研究还表明，2a、2c、2f和2j与其他化合物的标准品相比，显示出对过氧化物酶和 DNA 促旋酶蛋白的最高结合能。总体而言，2c和2f比其他标题化合物在体外和计算机中表现出最有前途的抗氧化和抗菌活性。因此，2c和2f
• Howard et al., Journal of the American Pharmaceutical Association (1912), 1954, vol. 43, p. 628,630
  作者：Howard et al.

  DOI：——

  日期：——
• US7576245B2
  申请人：——

  公开号：US7576245B2

  公开（公告）日：2009-08-18