(E)-2-(benzo[d]thiazol-2-yl)-3-(1H-indol-3-yl)acrylonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: (E)-2-(benzo[d]thiazol-2-yl)-3-(1H-indol-3-yl)acrylonitrile
• 英文别名: (2E)-2-(1,3-benzothiazol-2-yl)-3-(1H-indol-3-yl)prop-2-enenitrile；(E)-2-(1,3-benzothiazol-2-yl)-3-(1H-indol-3-yl)prop-2-enenitrile
• 化学式: C₁₈H₁₁N₃S
• 分子量: 301.371
• InChiKey: KKZSLQGVLBCOIH-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基苯硫醇 在 溶剂黄146 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.0h， 生成 (E)-2-(benzo[d]thiazol-2-yl)-3-(1H-indol-3-yl)acrylonitrile
  参考文献：
  名称：

  Mycobacterium tuberculosis lysine-ɛ-aminotransferase a potential target in dormancy: Benzothiazole based inhibitors

  摘要：

  MTB lysine-epsilon-aminotransferase (LAT) was found to play a crucial role in persistence and antibiotic tolerance. LAT serves as a potential target in the management of latent tuberculosis. In present work we attempted to derivatize the benzothiazole lead identified through high throughput virtual screening of Birla Institute of Technology and Science in house database. For Structure activity relationship purpose 22 derivatives were synthesized and characterized. Among synthesized compounds, eight compounds were found to be more efficacious in terms of LAT inhibition when compared to lead compound (IC50 10.38 +/- 1.21 mu M). Compound 22 exhibits bactericidal action against nutrient starved Mycobacterium tuberculosis (MTB). It also exhibits significant activity in nutrient starvation model (2.9 log folds) and biofilm model (2.3 log folds). 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.03.053

文献信息

• Tyrphostins. 5. Potent Inhibitors of Platelet-Derived Growth Factor Receptor Tyrosine Kinase:  Structure−Activity Relationships in Quinoxalines, Quinolines, and Indole Tyrphostins
  作者：Aviv Gazit、Harald App、Gerald McMahon、Jefferey Chen、Alexander Levitzki、Frank D. Bohmer

  DOI：10.1021/jm950727b

  日期：1996.1.1

  3-arylquinoxalines were prepared and tested for inhibition of platelet-derived growth factor receptor tyrosine kinase (PDGF-RTK) activity. The potency of the inhibitors was found to be quinoxalines > quinolines > indoles. Lipophilic groups (methyl, methoxy) in the 6 and 7 positions and phenyl at the 3 position of quinoxalines and quinolines were essential for potency, in contrast to the hydrophilic catechol

  制备了一系列3-吲哚丙烯腈酪氨酸酪蛋白，2-氯-3-苯基喹啉和3-芳基喹喔啉，并测试了其对血小板衍生的生长因子受体酪氨酸激酶（PDGF-RTK）活性的抑制作用。发现抑制剂的效力为喹喔啉>喹啉>吲哚。喹喔啉和喹啉在6和7位上的亲脂基团（甲基，甲氧基）和3位上的苯基对于效价至关重要，而酪蛋白中的亲水邻苯二酚基团在不同位点具有抑制EGFR激酶活性。抑制剂对PDGF具有选择性，对EGF受体和HER-2 / c-ErbB-2受体无活性。
• Biological evaluation of novel bicyclic heteroaromatic benzazole derived acrylonitriles: synthesis, antiproliferative and antibacterial activity
  作者：Nataša Perin、Maja Cindrić、Ivo Zlatar、L. Persoons、D. Daelemans、Vedrana Radovanović、Mihailo Banjanac、Karmen Brajša、Marijana Hranjec

  DOI：10.1007/s00044-022-02915-w

  日期：2022.8

  manuscript we present the design, synthesis and biological evaluation of novel benzazole derived acrylonitriles bearing bicyclic heteroaromatic rings. Either benzimidazole, benzothiazole or imidazo[4,5-b]pyridine scaffolds are linked via acrylonitrile linker with different bicyclic heteroaromatics. All newly prepared are evaluated for their in vitro antiproliferative activity on 8 human cancer cells as well

  在这份手稿中，我们介绍了新型苯唑衍生的带有双环杂芳环的丙烯腈的设计、合成和生物学评价。苯并咪唑、苯并噻唑或咪唑并[4,5- b ]吡啶支架通过丙烯腈接头与不同的双环杂芳烃连接。所有新制备的都在 MTS 细胞毒性和在 2D 和 3D 测定格式上进行的 BrdU 增殖测定中评估了它们对 8 种人类癌细胞以及三种人类肺癌细胞系的体外抗增殖活性。除萘基取代的苯并咪唑衍生物13和苯并噻唑基取代的衍生物17外，大多数测试化合物的活性均较弱, 都是苯并咪唑衍生的丙烯腈。此外，作为一种有前途的化合物，已证明是咪唑并[4,5- b ]吡啶衍生物25和30，对A549细胞具有选择性活性。此外，测试了所有化合物对九种细菌菌株和酿酒酵母的抗菌活性。只有苯并[ b ]呋喃-2-基取代的苯并咪唑衍生物14表现出中等活性。
• Mycobacterium tuberculosis lysine-ɛ-aminotransferase a potential target in dormancy: Benzothiazole based inhibitors
  作者：Rudraraju Srilakshmi Reshma、Variam Ullas Jeankumar、Nidhi Kapoor、Shalini Saxena、Karyakulam Andrews Bobesh、Astakala Rishi Vachaspathy、Pappachan E. Kolattukudy、Dharmarajan Sriram

  DOI：10.1016/j.bmc.2017.03.053

  日期：2017.5

  MTB lysine-epsilon-aminotransferase (LAT) was found to play a crucial role in persistence and antibiotic tolerance. LAT serves as a potential target in the management of latent tuberculosis. In present work we attempted to derivatize the benzothiazole lead identified through high throughput virtual screening of Birla Institute of Technology and Science in house database. For Structure activity relationship purpose 22 derivatives were synthesized and characterized. Among synthesized compounds, eight compounds were found to be more efficacious in terms of LAT inhibition when compared to lead compound (IC50 10.38 +/- 1.21 mu M). Compound 22 exhibits bactericidal action against nutrient starved Mycobacterium tuberculosis (MTB). It also exhibits significant activity in nutrient starvation model (2.9 log folds) and biofilm model (2.3 log folds). 2017 Elsevier Ltd. All rights reserved.