2-(2-furfulidene)benzithiazole | 134407-82-2

• 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: 2-(2-furfulidene)benzithiazole
• 英文别名: (E)-2-(benzo[d]thiazol-2-yl)-3-(furan-2-yl)acrylonitrile；(E)-2-(benzothiazol-2-yl)-3-(furan-2-yl)acrylonitrile；2-Benzothiazol-2-yl-3-furan-2-yl-acrylonitrile；(E)-2-(1,3-benzothiazol-2-yl)-3-(furan-2-yl)prop-2-enenitrile
• CAS: 134407-82-2
• 化学式: C₁₄H₈N₂OS
• 分子量: 252.296
• InChiKey: DBIXCVADFDLNNY-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 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：
  78.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氰乙酰肼 、 2-(2-furfulidene)benzithiazole 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以67%的产率得到2-Benzothiazol-2-yl-3-furan-2-yl-3-(5-imino-3-oxo-pyrazolidin-1-yl)-propionitrile
  参考文献：
  名称：

  Ghoneim, K. M.; El-Basil, S.; Osman, A. N., Revue Roumaine de Chimie, 1991, vol. 36, # 11-12, p. 1355 - 1362

  摘要：

  DOI：
• 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 2-(2-furfulidene)benzithiazole
  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

• Ultrasound-assisted phase-transfer catalysis method in an aqueous medium to promote the Knoevenagel reaction: Advantages over the conventional and microwave-assisted solvent-free/catalyst-free method
  作者：Pedro De-la-Torre、Edison Osorio、Jans H. Alzate-Morales、Julio Caballero、Jorge Trilleras、Luis Astudillo-Saavedra、Iván Brito、Alejandro Cárdenas、Jairo Quiroga、Margarita Gutiérrez

  DOI：10.1016/j.ultsonch.2014.02.021

  日期：2014.9

  catalyst-free conditions. The effects of conditions on reaction parameters were evaluated and compared in terms of reaction time, yield, purity and outcomes. The US-PTC method is more efficient than the MWI and conventional methods. The reaction times were considerably shorter, with high yields (>90%) and good levels of purity. In addition, X-ray diffraction analysis and quantum mechanical calculations

  考虑到丙烯腈衍生物作为荧光探针，AChE抑制剂等的广泛用途，有必要寻找一种简单，有效和简单的方法来合成和多样化这些化合物。我们报告了三种技术对杂环醛与2-（苯并[d]噻唑-2-基）乙腈之间反应的影响的比较研究结果：与PTC条件耦合的超声（US-PTC）; 在无溶剂和无催化剂条件下进行MW辐射（MWI）。评估条件对反应参数的影响，并根据反应时间，产率，纯度和结果进行比较。US-PTC方法比MWI和常规方法更有效。反应时间大大缩短，产率高（> 90％），纯度高。此外，X射线衍射分析和量子力学计算，在密度泛函理论（DFT）的水平上，批准获得具有E构型的丙烯腈异构体。3c的晶体结构通过弱C-Ho⋯N分子间相互作用（Ho⋯NC = 2.45Å，Co⋯NC = 3.348（3）Å，Ho⋯NC = 162°）稳定，形成中心对称环R2（2）（ 20）沿晶体学a轴。
• 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。
• Elgemeie, Galal Eldin Hamza; Aal, Fatma Abd El Maksoud Abd El, Heterocycles, 1986, vol. 24, # 2, p. 349 - 353
  作者：Elgemeie, Galal Eldin Hamza、Aal, Fatma Abd El Maksoud Abd El

  DOI：——

  日期：——
• Kada, Rudolf; Ilavsky, Dusan; Goljer, Igor, Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 2, p. 418 - 424
  作者：Kada, Rudolf、Ilavsky, Dusan、Goljer, Igor、Gaher, Peter

  DOI：——

  日期：——
• 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.