(E)-5-methyl-2-phenyl-3-(thiophen-2-yl)-7-(thiophen-2-ylmethylene)-3,3a,4,5,6,7-hexahydro-2H-pyrazolo[4,3-c]pyridine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-5-methyl-2-phenyl-3-(thiophen-2-yl)-7-(thiophen-2-ylmethylene)-3,3a,4,5,6,7-hexahydro-2H-pyrazolo[4,3-c]pyridine
• 英文别名: (7E)-5-methyl-2-phenyl-3-(2-thienyl)-7-(2-thienylmethylene)-3,3a,4,6-tetrahydropyrazolo[4,3-c]pyridine；(7E)-5-methyl-2-phenyl-3-thiophen-2-yl-7-(thiophen-2-ylmethylidene)-3,3a,4,6-tetrahydropyrazolo[4,3-c]pyridine
• 化学式: C₂₂H₂₁N₃S₂
• 分子量: 391.561
• InChiKey: CXSQILIHTWRLFQ-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  75.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-甲基-4-哌啶酮 在 sodium hydroxide 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 10.17h， 生成 (E)-5-methyl-2-phenyl-3-(thiophen-2-yl)-7-(thiophen-2-ylmethylene)-3,3a,4,5,6,7-hexahydro-2H-pyrazolo[4,3-c]pyridine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Certain α,β-Unsaturated Ketones and Their Corresponding Fused Pyridines as Antiviral and Cytotoxic Agents

  摘要：

  A new series of 3,5-bis(arylidene)-4-piperidones, as chalcone analogues carrying variety of aryl and heteroaryl groups, pyrazolo[4,3-c]pyridines, pyrido[4,3-d]pyrimidines, and pyrido[3,2-c]-pyridines, carrying an arylidene moiety, and a series of pyrano[3,2-c]pyridines, as flavone and coumarin isosteres, were synthesized and screened for their in vitro antiviral and antitumor activities at the National Cancer Institute (NCI). Compounds 9 and 18 proved to be active against herpes simplex virus-1 (HSV-1), while compound 13 showed moderate activity against human immunodeficiency virus-1 (HIV-1). Compounds 14, 26, 28, 33, and 35 exhibited a broad spectrum antitumor activity. In addition, compounds 26, 33, and 35 proved to be of moderate selectivity toward leukemia cell lines. The pyrano[3,2-c]pyridines heterocyclic system proved to be the most active antitumors among the investigated heterocycles.

  DOI：

  10.1021/jm000038m

文献信息

• Synthesis and discovery of pyrazolo-pyridine analogs as inflammation medications through pro- and anti-inflammatory cytokine and COX-2 inhibition assessments
  作者：J. Dennis Bilavendran、A. Manikandan、P. Thangarasu、K. Sivakumar

  DOI：10.1016/j.bioorg.2019.103484

  日期：2020.1

  of methanol. In the second and final step, compounds 3a-l were refluxed with phenyl-hydrazine to achieve the target compounds (E)-5-methyl-2-phenyl-3-(thiophen-2-yl)-7-(thiophen-2-ylmethylene)-3,3a,4,5,6,7-hexahydro-2H-pyrazolo[4,3-c]pyridine and their analogs (5a-l) in good yield. These compounds were used to assess their inflammation regulation properties in macrophages by executing quantitative pro-inflammatory

  本文简要介绍了为合成，表征和开发（E）-5-甲基-2-苯基-3-（噻吩-2-基）-7-（噻吩-2-基亚甲基）-3,3a，4所做的努力，5,6,7-六氢-2H-吡唑并[4,3-c]吡啶及其类似物。在两步反应中，第一步是通过搅拌反应合成（3Z，5E）-1-甲基-3,5-双（噻吩-2-基亚甲基）哌啶-4-酮衍生物（3a-1）甲醇存在下1-甲基哌啶-4-酮和取代噻吩-甲醛的混合物。在第二个也是最后一个步骤中，化合物3a-1与苯基肼一起回流，以实现目标化合物（E）-5-甲基-2-苯基-3-（噻吩-2-基）-7-（噻吩-2 （-亚甲基）-3,3a，4,5,6,7-六氢-2H-吡唑并[4,3-c]吡啶及其类似物（5a-1），收率很高。通过分别执行定量促炎和抗炎蛋白（例如TNF-α，IL-1β，IL6和IL-10），这些化合物可用于评估巨噬细胞中的炎症调节特性。电子和体外COX-2抑制研究有助于了解化合物