3-pyridylmethylenecyanothioacetamide | 109619-20-7

• 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: 3-pyridylmethylenecyanothioacetamide
• 英文别名: 2-Cyano-3-pyridin-3-ylprop-2-enethioamide
• CAS: 109619-20-7
• 化学式: C₉H₇N₃S
• 分子量: 189.241
• InChiKey: PNSDADFWVJVLIG-UHFFFAOYSA-N

物化性质

• 熔点：
  172 °C (decomp)
• 沸点：
  377.6±52.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

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：

  3-pyridylmethylenecyanothioacetamide 在 吗啉 氢氧化钾 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-Amino-6-methyl-4-(3-pyridyl)-thieno<2,3-b>pyridin-2-carbonsaeureethylester
  参考文献：
  名称：

  Sharanin, Yu. A.; Shestopalov, A. M.; Litvinov, V. P., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 9, p. 1762 - 1770

  摘要：

  DOI：
• 作为产物：
  描述：

  3-吡啶甲醛 、 2-氰基硫代乙酰胺 以 乙醇 为溶剂， 反应 0.5h， 生成 3-pyridylmethylenecyanothioacetamide
  参考文献：
  名称：

  官能化腈和6-烷基硫烷基-1,4-二氢烟酸酯的新多组分合成

  摘要：

  摘要丙二腈，硫化氢，芳基或杂芳基醛，1,3-二羰基化合物和烷基化试剂的多组分缩合可提供官能化的腈和6-烷基硫烷基-1,4-二氢烟酸的酯，它们的芳香族类似物和1,4-二氢噻吩并[ 2,3- b ]吡啶。

  DOI：

  10.1134/s1070363220030068

文献信息

• 10.1080/15257770.2017.1297454
  作者：Elgemeie, Galal H.、Fathy, Nahed M.、Farag, Ayman B.、Alkursani, Sheikha A.

  DOI：10.1080/15257770.2017.1297454

  日期：——

  A convenient synthesis of a novel series of dihydropyridine and pyridine thioglycosides was developed. The evaluation of anti-proliferative activity against HepG-2 cell lines (liver carcinoma cell lines) shows that most of the compounds have antitumor activity, especially 5b, 5f, 5j, 5n, 7b, 7f, 7j, 7n, 8b, 8f, and 8j. The results of molecular docking reveal that these compounds have high binding affinity

  开发了一种方便的新型二氢吡啶和吡啶硫代糖苷的合成方法。对HepG-2细胞系（肝癌细胞系）的抗增殖活性评估显示，大多数化合物具有抗肿瘤活性，尤其是5b，5f，5j，5n，7b，7f，7j，7n，8b，8f，和8j。分子对接的结果表明，这些化合物通过与胸苷酸合酶二氢叶酸还原酶（TS-DHFR）的结合口袋形成氢键而具有高结合亲和力。
• Reactions of sulfur ylides with α,β-unsaturated thioamides: Synthesis of dihydrothiophenes and cyclopropanes
  作者：A. V. Samet、A. M. Shestopalov、V. N. Nesterov、V. V. Semenov

  DOI：10.1007/bf02495519

  日期：1998.1

  The reactions of stabilized sulfonium ylides with arylmethylenecyanothioacetamides proceed stereoselectively to yield 2-amino-4,5-dihydrothiophenes and cyclopropane-thiocarboxamides. The structures of the latter compounds were confirmed by X-ray diffraction analysis.

  稳定的锍叶立德与芳基亚甲基氰硫代乙酰胺的反应立体选择性地进行，产生 2-氨基-4,5-二氢噻吩和环丙烷-硫代甲酰胺。后一种化合物的结构通过 X 射线衍射分析得到证实。
• Stereoselective Synthesis of<i>trans</i>-4,5-Substituted 1,4,5,6-tetrahydropyridine-2-(olates)thiolates
  作者：A. M. Shestopalov、V. P. Litvinov、L. A. Rodinovskaya、Yu. A. Sharanin

  DOI：10.1055/s-1991-26477

  日期：——

  trans-4,5-Substituted 1,4,5,6-tetrahydropyridine-2-(olates)thiolates are prepared either from pyridinium salts and cyanoacetic acid derivatives or from pyridinium salts, aromatic aldehydes and ethyl cyanoacetate or cyanoacetamide in the presence of a base.

  反式-4,5-取代的 1,4,5,6-四氢吡啶-2-（橄榄酸盐）硫醇酯可由吡啶鎓盐和氰乙酸衍生物制备，或由吡啶鎓盐、芳香醛和氰乙酸乙酯或氰乙酰胺在碱存在下制备。
• NUCLEIC ACID COMPONENTS AND THEIR ANALOGUES: A NOVEL AND EFFICIENT METHOD FOR THE SYNTHESIS OF A NEW CLASS OF BIPYRIDYL AND BIHETEROCYCLIC-NITRO GEN THIOGLYCOSIDES FROM PYRIDINE-2(1H)-THIONES
  作者：Galal H. Elgemeie、Mervat M. El-Enany、Mohamed M. Ismail、Eman K. Ahmed

  DOI：10.1081/ncn-120014820

  日期：——

  ABSTRACT A novel synthesis of a new class of bipyridyl and biheterocyclic-nitrogen thioglycosides utilizing the reactions of heterocyclic substituted pyridine-2(1H)-thiones and α-bromoglucose or α-bromogalactose tetraacetate as starting components is described.

  摘要描述了利用杂环取代的吡啶-2(1H)-硫酮和 α-溴葡萄糖或 α-溴半乳糖四乙酸酯作为起始组分的反应，合成了一类新的联吡啶和双杂环氮硫糖苷。
• Design, synthesis, antimicrobial evaluation and molecular docking studies of some new thiophene, pyrazole and pyridone derivatives bearing sulfisoxazole moiety
  作者：Tamer Nasr、Samir Bondock、Sameh Eid

  DOI：10.1016/j.ejmech.2014.07.052

  日期：2014.9

  Development of new antimicrobial agents is a good solution to overcome drug-resistance problems. In this context, new functionalized thiophene, acrylamide, arylhydrazone, pyrazole and pyridone derivatives bearing sulfisoxazole moiety were designed, synthesized and evaluated for their in vitro antibacterial and antifungal activities. Among the synthesized compounds, thiophene 4d and 6-thioglucosylpyridone 17 displayed significant antibacterial activities against Escherichia coli (MIC, 0.007 μg/mL vs gentamycin 1.95 μg/mL) and Bacillis subtilis (MIC, 0.007 μg/mL vs ampicillin 0.24 μg/mL), respectively. Whereas, the pyrazole 6 showed the highest antifungal activity against Aspergillus fumigates (MIC, 0.03 μg/mL vs amphotericin B 0.12 μg/mL). In general, most of the synthesized compounds exhibited better antimicrobial activities than sulfisoxazole; this might be attributed to the synergistic effect of the sulfonamide and attached heterocyclic moieties as well as the increased lipophilic characters of the synthesized compounds. Molecular docking studies indicated that the synthesized compounds could occupy both p-amino benzoic acid (PABA) and pterin binding pockets of the dihydropteroate synthase (DHPS), suggesting that the target compounds could act by the inhibition of microbial DHPS enzyme. The results provide important information for the future design of more potent antimicrobial agents.