(E)-3-(benzo[d][1,3]dioxol-5-yl)-2-(benzo[d]thiazol-2-yl)acrylonitrile | 1246081-67-3

• 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)-3-(benzo[d][1,3]dioxol-5-yl)-2-(benzo[d]thiazol-2-yl)acrylonitrile
• 英文别名: (E)-3-(benzo[d][1,3]dioxol-6-yl)-2-(benzo[d]thiazol-2-yl)acrylonitrile；(E)-3-(1,3-benzodioxol-5-yl)-2-(1,3-benzothiazol-2-yl)prop-2-enenitrile
• CAS: 1246081-67-3
• 化学式: C₁₇H₁₀N₂O₂S
• 分子量: 306.345
• InChiKey: PUVADSIVYFBGRV-KPKJPENVSA-N

物化性质

• 熔点：
  219-220 °C(Solv: toluene (108-88-3))
• 沸点：
  497.7±55.0 °C(Predicted)
• 密度：
  1.432±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  83.4
• 氢给体数：
  0
• 氢受体数：
  5

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)-3-(benzo[d][1,3]dioxol-5-yl)-2-(benzo[d]thiazol-2-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

• Reaction of <i>(E)</i>-3-(Benzo[d][1,3]dioxol-5-yl)-2- Cyanoacryloyl Chloride with Nucleophilic Reagents Containing Nitrogen and Sulfur
  作者：S. A. Shiba、A. K. El-Ziaty、N. K. El-Aasar、H. A. Al-Saman

  DOI：10.1080/10426500903176547

  日期：2010.7.30

  (E)-3-(Benzo[d][1,3]dioxol-5-yl)-2-cyanoacryloyl chloride was reacted with nucleophilic reagents containing nitrogen and sulfur to give new acryloyl amides, imides, thioesters, and heterocyclic systems. Some of these products showed moderate activities against antibacterial and antifungal agents. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus

  (E)-3-(苯并[d][1,3]二氧六环-5-基)-2-氰基丙烯酰氯与含氮和硫的亲核试剂反应，得到新的丙烯酰胺、酰亚胺、硫酯和杂环体系。其中一些产品对抗菌剂和抗真菌剂显示出中等活性。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。
• Microwave-assisted synthesis under solvent-free conditions of (E)-2-(Benzo[d]thiazol-2-yl)-3-arylacrylonitriles
  作者：Jorge E. Trilleras、Kelly J. Velasquez、Dency J. Pacheco、Jairo Quiroga、Alejandro Ortíz

  DOI：10.1590/s0103-50532011001200022

  日期：——

  A series of (E)-2-(benzo[d]thiazol-2-yl)-3-arylacrylonitriles was synthesized by microwave assisted Knoevenagel condensation under solvent-free conditions from the corresponding 2-(benzo[d]thiazol-2-yl) acetonitrile and aromatic aldehydes with electrondonating/electron-withdrawing groups. The reaction times were considerably short and the products obtained in moderate yields (50 to 75%) and good purity. The configuration of the acrylonitrile double bond could not be established by regular NMR methods. However, theoretical studies suggest that the E isomer is more stable than Z, which is in good agreement with some experimental evidences.
• 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.