(E)-2-(benzo[d]thiazol-2-yl)-3-(3,4,5-trimethoxyphenyl)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-(3,4,5-trimethoxyphenyl)acrylonitrile
• 英文别名: (2E)-2-(1,3-benzothiazol-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-enenitrile；(E)-2-(1,3-benzothiazol-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-enenitrile
• 化学式: C₁₉H₁₆N₂O₃S
• 分子量: 352.414
• InChiKey: GULOANVCIIOIBH-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  92.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  异腈基乙酸甲酯 、 (E)-2-(benzo[d]thiazol-2-yl)-3-(3,4,5-trimethoxyphenyl)acrylonitrile 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以70%的产率得到methyl 3-(benzo[d]thiazol-2-yl)-3-cyano-4-(3,4,5-trimethoxyphenyl)-3,4-dihydro-2H-pyrrole-5-carboxylate
  参考文献：
  名称：

  使用2-异氰基乙酸酯轻松合成新的功能化3,4-二氢-2 H-吡咯

  摘要：

  据报道，由2-异氰基乙酸酯和容易合成的丙烯腈一步合成新型的官能化的3，4-二氢-2 H-吡咯。反应在温和的条件下高效高效地进行。通过X射线晶体学分析确认了两个代表性结构3a和3m的结构。

  DOI：

  10.1016/j.tetlet.2020.151944
• 作为产物：
  描述：

  2-氨基苯硫醇 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (E)-2-(benzo[d]thiazol-2-yl)-3-(3,4,5-trimethoxyphenyl)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

• Biological activity and computational analysis of novel acrylonitrile derived benzazoles as potent antiproliferative agents for pancreatic adenocarcinoma with antioxidative properties
  作者：Anja Beč、Leentje Persoons、Dirk Daelemans、Kristina Starčević、Robert Vianello、Marijana Hranjec

  DOI：10.1016/j.bioorg.2024.107326

  日期：2024.6

  anticancer properties of acrylonitriles, we present a study involving the design, synthesis, computational analysis, and biological assessment of novel acrylonitriles derived from methoxy, hydroxy, and -substituted benzazole. Our aim was to examine how varying the number of methoxy and hydroxy groups, as well as the -substituents on the benzimidazole core, influences their biological activity. The newly

  我们继续研究丙烯腈的抗癌特性，提出了一项涉及源自甲氧基、羟基和取代苯并唑的新型丙烯腈的设计、合成、计算分析和生物学评估的研究。我们的目的是研究改变甲氧基和羟基的数量以及苯并咪唑核心上的β-取代基如何影响其生物活性。新合成的丙烯腈对 Capan-1 胰腺癌细胞系表现出强效、选择性的抗增殖作用，IC 值范围为 1.2 至 5.3 μM。因此，我们在其他三种胰腺腺癌细胞系中进一步评估了这些化合物，同时还研究了它们对正常 PBMC 细胞的影响以确定选择性。在这些化合物中，单羟基取代的苯并咪唑衍生物具有最深刻和最广谱的抗癌抗增殖活性，成为有前途的主要候选化合物。此外，FRAP 测定（范围为 3200 至 5235 mmolFe/mmolC）表明，该系列中的大多数丙烯腈都表现出显着的抗氧化活性，超过了参考分子 BHT。计算分析强调了电子电离在赋予抗氧化特性方面的普遍性，计算出的电离能与观察到的活性密切相关。
• Ghoneim, K. M.; El-Basil, S.; Osman, A. N., Revue Roumaine de Chimie, 1991, vol. 36, # 11-12, p. 1355 - 1362
  作者：Ghoneim, K. M.、El-Basil, S.、Osman, A. N.、Said, M. M.、Megahed, S. A.

  DOI：——

  日期：——
• 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.