2-cyano-3-(3'-pyridyl)acrylthioamide | 109628-96-8

• 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: 2-cyano-3-(3'-pyridyl)acrylthioamide
• 英文别名: 2-cyano-3-(pyrid-3'-yl)-1,4,5,6-tetrahydropyridine-2-thiolate；2-Cyano-3-(pyrid-3'-yl)-acrylthioamide；2-cyano-3-pyridin-3-ylprop-2-enethioamide；2-Cyano-3-pyridin-3-yl-thioacrylamide；(E)-2-cyano-3-pyridin-3-ylprop-2-enethioamide
• CAS: 109628-96-8
• 化学式: C₉H₇N₃S
• 分子量: 189.241
• InChiKey: PNSDADFWVJVLIG-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 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：
  94.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-cyano-3-(3'-pyridyl)acrylthioamide 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 6-phenyl-5-ethoxycarbonyl-3-cyano-4-(pyrid-3'-yl)-1,4-dihydropyridine-2-thione betaine
  参考文献：
  名称：

  Synthesis, properties, and cardiotonic activity of some 2-carbamoylmethylthio-6-phenyl-5-ethoxycarbonyl-3-cyano-4-[pyrid-3-yl]pyridines and their hydrogenated analogs

  摘要：

  DOI：

  10.1007/bf00772903
• 作为产物：
  描述：

  3-吡啶甲醛 、 2-氰基硫代乙酰胺 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 2-cyano-3-(3'-pyridyl)acrylthioamide
  参考文献：
  名称：

  Synthesis, Reactions, and Antiviral Activity of 6′-Amino-2′-thioxo-1′,2′-dihydro-3,4′-bipyridine-3′,5′-dicarbonitrile

  摘要：

  Nicotinaldehyde 1 reacted with 2-cyanoethanethioamide 2 to give 2-cyano-3-pyridin-3-ylprop-2-enethioamide 3, which reacted with a second mole of 2 to give the corresponding 6'-amino-2'-thioxo-1',2'-dihydro-3,4'-bipyridine-3',5'-dicarbonitrile 6. The synthetic potentiality of compound 6 was investigated via its reaction with active halogen-containing reagents, e.g., chloroacetone, 2-chloro-3-oxobutanoate, 2-chloroacetamide, chloroaceto-nitrile, and ethyl chloroacetate, to afford the corresponding thieno[2,3-b]-pyridine derivatives. Structure elucidation of all newly synthesized heterocyclic compounds was based on the data of elemental analyses, and IR, (HNMR)-H-1, as well as mass spectra. Cytotoxicity, anti-HSV1, anti-HAV, and MBB activities were evaluated for all newly synthesized heterocyclic compounds.

  DOI：

  10.1080/10426500601087277

文献信息

• 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«
• Synthesis and cardiovascular activity of 4-substituted 2-alkylthio-1,4-dihydropyridines
  作者：A. A. Krauze、R. O. Vitolinya、M. R. Romanova、G. Ya. Dubur

  DOI：10.1007/bf00763628

  日期：1988.8
• Recyclization of morpholinium 3,4-trans-4-aryl-5-cyano-2-hydroxy-3-nitro-1,2,3,4-tetrahydropyridine-6-thiolates to 2-acylamino-5-amino-4-aryl-3-cyanothiophenes. Molecular and crystal structures of 5-amino-3-cyano-2-(4-methylbenzamido)-4-(2-thienyl)-thiophene
  作者：Ludmila A. Rodinovskaya、Anatoly M. Shestopalov、Konstantin S. Chunikhin

  DOI：10.1016/s0040-4020(02)00361-7

  日期：2002.5

  2-Acylamino-5-amino-4-aryl-3-cyanothiophenes were synthesized by the reaction of arylidenecyanothioacetamides with alpha-nitroketones or by the three-component reaction of aromatic aldehydes, alpha-nitroketones, and cyanothioacetamide, or the reaction of 3-(4-chlorophenyl)-2-nitro-1-phenyl-2-propen-1-one with cyanothioacetamide in the presence of morpholine. These diaminothiophenes are formed via the recyclization stage of the primarily formed tetrahydropyridines, morpholinium 3,4-trans-4-aryl-5-cyano-2-hydroxy-3-nitro-1,2,3,4-tetrahydropyridine-6-thiolates. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A Total Synthesis of a New Class of Biazine Thioglycosides
  作者：Galal H. Elgemeie、Mona M. Hussein、Sheakha A. Al‐Khursani

  DOI：10.1081/car-200045262

  日期：2004.1

  A new method for the synthesis of bipyridinyl S-glycosides 11 and 12 has provided the title compounds in a higher yield. Application of a one-pot glycosylation methodology resulted in an efficient, high-yield synthesis of biazine S-glycosides 17-20 An X-ray diffraction analysis of 11 disclosed the conformation of this glycoside as the S-glycoside and not the corresponding N-form.
• Preparation and properties of betaines of 4-pyridyl-3,4-dihydropyridine-2-thiones(1H)
  作者：A. A. Krauze、�. �. Liepin'sh、Yu. �. Pelcher、Z. A. Kalme、G. Ya. Dubur

  DOI：10.1007/bf00519531

  日期：1986.5