(E)-2-(1,3-benzothiazol-2-yl)-3-(4-fluoroiphenyl)acrylonitrile | 1363533-12-3

• 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)-2-(1,3-benzothiazol-2-yl)-3-(4-fluoroiphenyl)acrylonitrile
• 英文别名: (E)-2-(benzo[d]thiazol-2-yl)-3-(4-fluorophenyl)acrylonitrile；(2E)-2-(1,3-benzothiazol-2-yl)-3-(4-fluorophenyl)prop-2-enenitrile；(E)-2-(1,3-benzothiazol-2-yl)-3-(4-fluorophenyl)prop-2-enenitrile
• CAS: 1363533-12-3
• 化学式: C₁₆H₉FN₂S
• 分子量: 280.325
• InChiKey: FOZUSBHYTRVVMA-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-3-phenyl-propionaldehyde 、 (E)-2-(1,3-benzothiazol-2-yl)-3-(4-fluoroiphenyl)acrylonitrile 在 BF₄^(1-)*C₂₁H₂₂N₃O⁽¹⁺⁾ 、 N,N-二异丙基乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 16.0h， 以97%的产率得到
  参考文献：
  名称：

  Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes

  摘要：

  Diastereo- and enantioselective N-heterocyclic carbene catalyzed 1-azadiene Diels-Alder reactions of (E)-2-styrylbenzothiazoles with alpha-chloro aldehydes are reported. This annulation strategy provides an efficient access to medicinally important dihydrobenzothiazolopyridin-1-ones in good to excellent yields (44-97%) with very good to excellent stereoselectivities (up to 9: 1 dr, 98% ee) and tolerates quite a range of substituents.

  DOI：

  10.1055/s-0034-1379369
• 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-(1,3-benzothiazol-2-yl)-3-(4-fluoroiphenyl)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

• (<i>E</i>)-2-(1,3-Benzothiazol-2-yl)-3-(4-fluorophenyl)acrylonitrile: a chain of π-stacked hydrogen-bonded rings
  作者：Jorge Trilleras、Kelly Velásquez、Justo Cobo、Christopher Glidewell

  DOI：10.1107/s0108270113013267

  日期：2013.6.15

  The title compound, C₁₆H₉FN₂S, crystallizes as a nonmerohedral twin with twin rotation about the reciprocal-lattice vector [10\overline1}]*. The molecules are nearly planar and the dihedral angle between the planes of the two aryl rings is only 4.4 (2)°. The molecules are linked by pairs of C—H...N hydrogen bonds to form cyclic centrosymmetricR₂²(18) dimers, which are linked into chains by an aromatic π–π stacking interaction. Comparisons are made with some related 3-aryl-2-thienylacrylonitriles.

  标题化合物 C16H9FN2S 结晶为非单面孪晶，孪晶围绕倒易晶格矢量 [10\overline1}]* 旋转。分子几乎是平面的，两个芳基环平面之间的二面角仅为 4.4 (2)°。分子通过成对的 C-H...N 氢键连接，形成环状中心对称的 R22(18) 二聚体，这些二聚体通过芳香族的 π-π 堆积相互作用连接成链。并与一些相关的 3-芳基-2-噻吩丙烯腈进行了比较。
• Cu-Catalyzed, electron-relayed three-component synthesis of 2-alkenylbenzothiazoles with cathodic ammonia evolution
  作者：Chengxian Hu、Dan Wang、Lu Wang、Ying Fu、Zhengyin Du

  DOI：10.1039/d3gc03884j

  日期：——

  A CuI-catalyzed, one-pot, three-component reaction of benzaldehydes, 2-aminobenzothiol and malononitrile is described, wherein CuI plays an electron relay. The method features simplified operation, highly atom economy, and mild reaction conditions.

  介绍了一种 CuI 催化的苯甲醛、2-氨基苯硫醇和丙二腈的一锅三组分反应，其中 CuI 起着电子中继的作用。该方法具有操作简单、原子经济性高和反应条件温和等特点。
• 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.
• Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes
  作者：Dieter Enders、Xiaoxiao Song、Qijian Ni、Chen Zhu、Gerhard Raabe

  DOI：10.1055/s-0034-1379369

  日期：——

  Diastereo- and enantioselective N-heterocyclic carbene catalyzed 1-azadiene Diels-Alder reactions of (E)-2-styrylbenzothiazoles with alpha-chloro aldehydes are reported. This annulation strategy provides an efficient access to medicinally important dihydrobenzothiazolopyridin-1-ones in good to excellent yields (44-97%) with very good to excellent stereoselectivities (up to 9: 1 dr, 98% ee) and tolerates quite a range of substituents.