(E)-2-cyano-3-pyridin-3-ylacrylamide | 40029-36-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (E)-2-cyano-3-pyridin-3-ylacrylamide
• 英文别名: 2-cyano-3-(3'-pyridyl)acrylamide；2-Cyano-3-(3-pyridyl)acrylamid；(E)-2-cyano-3-pyridin-3-ylprop-2-enamide
• CAS: 40029-36-5
• 化学式: C₉H₇N₃O
• 分子量: 173.174
• InChiKey: HBHVANPHMSEPFC-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-吡啶基)丙酮 、 (E)-2-cyano-3-pyridin-3-ylacrylamide 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 5.5h， 以27%的产率得到3-cyano-6-methyl-4-(3'-pyridyl)-5-(4'-pyridyl)pyridine-2(1H)-one
  参考文献：
  名称：

  4,5-二吡啶并吡啶-2(1H)-酮、吡啶-2(1H)-硫酮和作为强心药米力农类似物的相关衍生物的合成

  摘要：

  4,5-二炔基取代的 pvndine-2(1H)-one 8 和 pvndine-2(1H)-硫酮 12 已通过 4-吡啶丙酮 3 和 2-氰基-3-(3-pvridyl)丙烯酰胺的迈克尔反应制备（硫丙烯酰胺）（4j 9），随后进行杂环化、脱水和脱氢。硫酮14的钠盐，作为水溶性化合物已经通过用甲醇钠处理硫酮12而获得。12 氧化生成 2,2-双吡啶基二硫化物 13，但甲基化生成 2-methykhiopvndine 15 引言 充血性心力衰竭 (CHF) 是一种广泛存在且高度恶性的疾病。治疗 CHF​​ 的最有希望的发展是非糖苷、非拟交感神经正性肌力（强心剂）药物。这些药物的主要机制是通过抑制环核苷酸磷酸二酯酶升高心肌细胞中的 cAMP 水平 [1-3]。3、15 年来，4'联吡啶作为强心剂一直备受关注。其中米力农1[I, 4-8]已被发现。米力农的硫类似物th;ouc 2 [9] 及其Za«

  DOI：

  10.1515/hc.2001.7.5.427
• 作为产物：
  描述：

  3-吡啶甲醛 、 氰乙酰胺 在 N-甲基哌嗪 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以59%的产率得到(E)-2-cyano-3-pyridin-3-ylacrylamide
  参考文献：
  名称：

  Arylcyanoacrylamides as inhibitors of the Dengue and West Nile virus proteases

  摘要：

  The 3-aryl-2-cyanoacrylamide scaffold was designed as core pharmacophore for inhibitors of the Dengue and West Nile virus serine proteases (NS2B-NS3). A total of 86 analogs was prepared to study the structure-activity relationships in detail. Thereby, it turned out that the electron density of the aryl moiety and the central double bond have a crucial influence on the activity of the compounds, whereas the influence of substituents of the amide residue is less relevant. The para-hydroxy substituted analog was found to be the most potent inhibitor in this series with a K(i)-value of 35.7 mu M at the Dengue and 44.6 mu M at the West Nile virus protease. The aprotinin competition assay demonstrates a direct interaction of the inhibitor molecule with active centre of the Dengue virus protease. The target selectivity was studied in a counterscreen with thrombin and found to be 2.8:1 in favor of DEN protease and 2.3:1 in favor of WNV protease, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.061

文献信息

• SHESTOPALOV, A. M.;BOGOMOLOVA, O. P.;LITVINOV, V. I., IZV. AN CCCP. CEP. XIM.,(1991) N, S. 1630-1637
  作者：SHESTOPALOV, A. M.、BOGOMOLOVA, O. P.、LITVINOV, V. I.

  DOI：——

  日期：——
• Arylcyanoacrylamides as inhibitors of the Dengue and West Nile virus proteases
  作者：Christoph Nitsche、Christian Steuer、Christian D. Klein

  DOI：10.1016/j.bmc.2011.10.061

  日期：2011.12

  The 3-aryl-2-cyanoacrylamide scaffold was designed as core pharmacophore for inhibitors of the Dengue and West Nile virus serine proteases (NS2B-NS3). A total of 86 analogs was prepared to study the structure-activity relationships in detail. Thereby, it turned out that the electron density of the aryl moiety and the central double bond have a crucial influence on the activity of the compounds, whereas the influence of substituents of the amide residue is less relevant. The para-hydroxy substituted analog was found to be the most potent inhibitor in this series with a K(i)-value of 35.7 mu M at the Dengue and 44.6 mu M at the West Nile virus protease. The aprotinin competition assay demonstrates a direct interaction of the inhibitor molecule with active centre of the Dengue virus protease. The target selectivity was studied in a counterscreen with thrombin and found to be 2.8:1 in favor of DEN protease and 2.3:1 in favor of WNV protease, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
• SYNTHESIS OF 4,5-DIPYRIDYLPYRIDIN-2(1H)-ONES, PYRIDINE- 2(1H)-THIONES AND RELATED DERIVATIVES AS ANALOGES OF CARDIOTONIC DRUG MILRINONE
  作者：A. Krauze、V. Garalene、R. Vitoliij、G. Duburs

  DOI：10.1515/hc.2001.7.5.427

  日期：2001.1

  developments of treatment of CHF are the non-glycoside, non-sympathomimetic positive inotropic (cardiotonic) agents. The principal mechanism of these agents is elevation of cAMP levels in the myocardial cell by inhibition of cyclic nucleotide phosphodiesterase [1-3]. 3,4'Dipyridyls have been of interest as cardiotonic agents for more than 15 years. Among them milrinone 1 [I , 4-8] has been discovered. The

  4,5-二炔基取代的 pvndine-2(1H)-one 8 和 pvndine-2(1H)-硫酮 12 已通过 4-吡啶丙酮 3 和 2-氰基-3-(3-pvridyl)丙烯酰胺的迈克尔反应制备（硫丙烯酰胺）（4j 9），随后进行杂环化、脱水和脱氢。硫酮14的钠盐，作为水溶性化合物已经通过用甲醇钠处理硫酮12而获得。12 氧化生成 2,2-双吡啶基二硫化物 13，但甲基化生成 2-methykhiopvndine 15 引言 充血性心力衰竭 (CHF) 是一种广泛存在且高度恶性的疾病。治疗 CHF​​ 的最有希望的发展是非糖苷、非拟交感神经正性肌力（强心剂）药物。这些药物的主要机制是通过抑制环核苷酸磷酸二酯酶升高心肌细胞中的 cAMP 水平 [1-3]。3、15 年来，4'联吡啶作为强心剂一直备受关注。其中米力农1[I, 4-8]已被发现。米力农的硫类似物th;ouc 2 [9] 及其Za«