ethyl (2E/Z)-2-(1,3-benzothiazol-2-yl)-3-(dimethylamino)acrylate | 71240-23-8

• 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: ethyl (2E/Z)-2-(1,3-benzothiazol-2-yl)-3-(dimethylamino)acrylate
• 英文别名: 2-benzothiazol-2-yl-3-dimethylamino-acrylic acid ethyl ester；Ethyl 2-(1,3-benzothiazol-2-yl)-3-(dimethylamino)prop-2-enoate
• CAS: 71240-23-8
• 化学式: C₁₄H₁₆N₂O₂S
• 分子量: 276.359
• InChiKey: RGHZVRCGIODCDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  70.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (2E/Z)-2-(1,3-benzothiazol-2-yl)-3-(dimethylamino)acrylate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 7.0h， 生成 2-cyclohexyl-1-oxo-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylic acid
  参考文献：
  名称：

  Pyridobenzothiazole derivatives as new chemotype targeting the HCV NS5B polymerase

  摘要：

  Hepatitis C virus (HCV) infection has been recognized as the major cause of liver failure that can lead to hepatocellular carcinoma. Among all the HCV proteins, NS5B polymerase represents a leading target for drug discovery strategies. Herein, we describe our initial research efforts towards the identification of new chemotypes as allosteric NS5B inhibitors. In particular, the design, synthesis, in vitro anti-NS5B and in cellulo anti-HCV evaluation of a series of 1-oxo-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylate derivatives are reported. Some of the newly synthesized compounds showed an IC50 ranging from 11 to 23 mu M, and molecular modeling and biochemical studies suggested that the thumb domain could be the target site for this new class of NS5B inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.061
• 作为产物：
  描述：

  氰乙酸乙酯 在 三氯氧磷 作用下， 生成 ethyl (2E/Z)-2-(1,3-benzothiazol-2-yl)-3-(dimethylamino)acrylate
  参考文献：
  名称：

  Pyridobenzothiazole derivatives as new chemotype targeting the HCV NS5B polymerase

  摘要：

  Hepatitis C virus (HCV) infection has been recognized as the major cause of liver failure that can lead to hepatocellular carcinoma. Among all the HCV proteins, NS5B polymerase represents a leading target for drug discovery strategies. Herein, we describe our initial research efforts towards the identification of new chemotypes as allosteric NS5B inhibitors. In particular, the design, synthesis, in vitro anti-NS5B and in cellulo anti-HCV evaluation of a series of 1-oxo-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylate derivatives are reported. Some of the newly synthesized compounds showed an IC50 ranging from 11 to 23 mu M, and molecular modeling and biochemical studies suggested that the thumb domain could be the target site for this new class of NS5B inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.061

文献信息

• Sustainable, three-component, one-pot procedure to obtain active anti-flavivirus agents
  作者：Tommaso Felicetti、Maria Sole Burali、Chin Piaw Gwee、Kitti Wing Ki Chan、Sylvie Alonso、Serena Massari、Stefano Sabatini、Oriana Tabarrini、Maria Letizia Barreca、Violetta Cecchetti、Subhash G. Vasudevan、Giuseppe Manfroni

  DOI：10.1016/j.ejmech.2020.112992

  日期：2021.1

  number of purification steps, the use of hazardous reagents and environmentally unsustainable generation of waste. Considering the promising antiviral activity of PBTZ analogues which require further exploration, in this work, we report the development of a new and sustainable three-component reaction (3CR) that can be combined with a basic hydrolysis in a one-pot procedure to obtain the PBTZ scaffold

  属于黄病毒属的蚊媒病毒，例如登革热病毒（DENV）和寨卡病毒（ZIKV），会引起人类感染，从轻度的流感样症状到出血热，肝炎和神经病。迄今为止，只有少数黄病毒的疫苗，而没有有效的治疗方法。 吡啶并苯并噻唑（PBTZ）衍生物是一类具有广阔前景的广谱抗黄病毒活性的化合物，据报道，其中大多数是黄病毒NS5聚合酶的有效抑制剂。然而，PBTZ类似物的合成需要大量的纯化步骤，危险试剂的使用以及对环境不可持续的废物的产生。 考虑到PBTZ类似物的有希望的抗病毒活性需要进一步探索，在这项工作中，我们报告了一种新的可持续的三组分反应（3CR）的开发，该反应可以与一锅法中的碱性水解反应结合使用PBTZ支架，从而减少了合成步骤，提高了产量并节省了时间。为了通过使用不同的起始材料来证明其广泛的应用范围，对3CR进行了广泛的研究。此外，利用这些程序，我们接下来设计和合成了一组新的PBTZ类似物，这些类似物已作为抗DE
• A new route to α-hetero β-enamino esters using a mild and convenient solvent-free process assisted by focused microwave irradiation
  作者：Zohra Dahmani、Mustapha Rahmouni、Richard Brugidou、Jean Pierre Bazureau、Jack Hamelin

  DOI：10.1016/s0040-4039(98)01894-2

  日期：1998.11

  New alpha-hetero beta-enamino esters 5 (X - NH, O, S) are obtained in good to excellent yields by transamination reactions from ethyl 3-dimethylamino acrylate 2(a-c) and various volatile amines 3(a-e) using solvent-free conditions assisted by focused microwave irradiation. Most of the alpha-hetero beta-enamino ester derivatives 3 present a (E)-s-cis/trans conformation. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Meddad; Rahmouni; Derdour, Synthesis, 2001, # 4, p. 581 - 584
  作者：Meddad、Rahmouni、Derdour、Bazureau、Hamelin

  DOI：——

  日期：——
• Kato,T. et al., Chemical and pharmaceutical bulletin, 1979, vol. 27, p. 1186 - 1189
  作者：Kato,T. et al.

  DOI：——

  日期：——