6-氨基-4-(1H-吲哚-3-基)-2-硫代-1,2-二氢吡啶-3,5-二腈 | 1001625-57-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 6-氨基-4-(1H-吲哚-3-基)-2-硫代-1,2-二氢吡啶-3,5-二腈
• 英文名称: 6-amino-4-(1H-indol-3-yl)-2-thioxo-1,2-dihydropyridine-3,5-dicarbonitrile
• 英文别名: 6-Amino-4-(1h-indol-3-yl)-2-thioxo-1,2-dihydro-pyridine-3,5-dicarbonitrile；2-amino-4-(1H-indol-3-yl)-6-sulfanylidene-1H-pyridine-3,5-dicarbonitrile
• CAS: 1001625-57-5
• 化学式: C₁₅H₉N₅S
• 分子量: 291.336
• InChiKey: OBMAJXLXVSBDGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-cyano-3-(1H-indol-3-yl)prop-2-enethioamide 在 盐酸 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 6-氨基-4-(1H-吲哚-3-基)-2-硫代-1,2-二氢吡啶-3,5-二腈
  参考文献：
  名称：

  A New Approach to the Synthesis of Functional Derivatives of 3-(4-Pyridinyl)-1H-indole and 4-(1H-Indol-3-yl)thieno[2,3-b]pyridine

  摘要：

  Sequential reaction of indole-3-carbaldehyde with cyanothioacetamide and KOH led to the formation of potassium 6-amino-4-(1H-indol-3-yl)-3,5-dicyanopyridine-2-thiolate. S-Alkylation of the latter afforded new functional derivatives of 3-(pyridine-4-yl)-1H-indole and 4-(1H-indol-3-yl)-thieno[2,3-b]pyridine.

  DOI：

  10.1134/s1070363218040114

文献信息

• 3,6-Diamino-4-(2-halophenyl)-2-benzoylthieno[2,3-<i>b</i>]pyridine-5-carbonitriles Are Selective Inhibitors of Plasmodium falciparum Glycogen Synthase Kinase-3
  作者：Wiebke Fugel、Anselm Erich Oberholzer、Bernhard Gschloessl、Ron Dzikowski、Narkiss Pressburger、Lutz Preu、Laurence H. Pearl、Blandine Baratte、Morgane Ratin、Ilya Okun、Christian Doerig、Sebastian Kruggel、Thomas Lemcke、Laurent Meijer、Conrad Kunick

  DOI：10.1021/jm301575n

  日期：2013.1.10

  Plasmodium falciparum is the infective agent responsible for malaria tropica. The glycogen synthase kinase-3 of the parasite (PfGSK-3) was suggested as a potential biological target for novel antimalarial drugs. Starting from hit structures identified in a high-throughput screening campaign, 3,6-diamino-4-(2-halophenyl)-2-benzoylthieno[2,3-b]pyridine-5-carbonitriles were discovered as a new class of PfGSK-3 inhibitors. Being less active on GSK-3 homologues of other species, the title compounds showed selectivity in favor of PfGSK-3. Taking into account the X-ray structure of a related molecule in complex with human GSK-3 (HsGSK-3), a model was computed for the comparison of inhibitor complexes with the plasmodial and human enzymes. It was found that subtle differences in the ATP-binding pockets are responsible for the observed PfGSK-3 vs HsGSK-3 selectivity. Representatives of the title compound class exhibited micromolar IC₅₀ values against P. falciparum erythrocyte stage parasites. These results suggest that inhibitors of PfGSK-3 could be developed as potential antimalarial drugs.
• A New Approach to the Synthesis of Functional Derivatives of 3-(4-Pyridinyl)-1H-indole and 4-(1H-Indol-3-yl)thieno[2,3-b]pyridine
  作者：V. V. Dotsenko、S. G. Krivokolysko、B. S. Krivokolysko、K. A. Frolov

  DOI：10.1134/s1070363218040114

  日期：2018.4

  Sequential reaction of indole-3-carbaldehyde with cyanothioacetamide and KOH led to the formation of potassium 6-amino-4-(1H-indol-3-yl)-3,5-dicyanopyridine-2-thiolate. S-Alkylation of the latter afforded new functional derivatives of 3-(pyridine-4-yl)-1H-indole and 4-(1H-indol-3-yl)-thieno[2,3-b]pyridine.