2-(5-氟-1,3-苯并噻唑-2-基)乙酸乙酯 | 1126637-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 2-(5-氟-1,3-苯并噻唑-2-基)乙酸乙酯
• 英文名称: ethyl (5-fluoro-1,3-benzothiazol-2-yl)acetate
• 英文别名: Ethyl 2-(5-fluorobenzo[D]thiazol-2-YL)acetate；ethyl 2-(5-fluoro-1,3-benzothiazol-2-yl)acetate
• CAS: 1126637-84-0
• 化学式: C₁₁H₁₀FNO₂S
• 分子量: 239.27
• InChiKey: GGFBEMGBBPMCLU-UHFFFAOYSA-N

物化性质

• 沸点：
  335.2±22.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(5-氟-1,3-苯并噻唑-2-基)乙酸乙酯 在 三氯氧磷 作用下， 反应 7.0h， 生成 ethyl 8-fluoro-1-oxo-2-phenyl-1H-pyrido[2,1-b]benzothiazole-4-carboxylate
  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：

  5-氯-2-甲基苯并噻唑 在 水 、 sodium hydroxide 作用下， 以 乙二醇 为溶剂， 反应 15.0h， 生成 2-(5-氟-1,3-苯并噻唑-2-基)乙酸乙酯
  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

• Palladium Catalyzed Controllable Mono‐ or Di‐Allylic Substitution Reaction of Benzothiazolylacetate with Allylic Alcohols
  作者：Peipei Yan、Shulei Pan、Jinjin Hu、Limei Lu、Xiaofei Zeng、Guofu Zhong

  DOI：10.1002/adsc.201801351

  日期：2019.3.15

  or di‐selective allylic substitution reaction of benzothiazolylacetate and allylic alcohols has been developed. The mono‐ and di‐selectivities could be efficiently controlled by changing the reaction solvent and temperature, affording various mono‐ and di‐allylated products in good to excellent yields and selectivities. Both linear and branched allylic alcohols as well as allyl alcohol could all be well

  现已开发出Pd（PPh 3）4 /酸催化苯并噻唑基乙酸酯和烯丙醇的高效单或双选择性烯丙基取代反应。通过改变反应溶剂和温度，可以有效地控制单和双选择性，从而提供各种单或二烯丙基化的产物，收率和选择性都非常好。线性和支链的烯丙基醇以及烯丙醇都可以在反应中被很好地耐受。
• Discovery of CX-5461, the First Direct and Selective Inhibitor of RNA Polymerase I, for Cancer Therapeutics
  作者：Mustapha Haddach、Michael K. Schwaebe、Jerome Michaux、Johnny Nagasawa、Sean E. O'Brien、Jeffrey P. Whitten、Fabrice Pierre、Pauline Kerdoncuff、Levan Darjania、Ryan Stansfield、Denis Drygin、Kenna Anderes、Chris Proffitt、Josh Bliesath、Adam Siddiqui-Jain、May Omori、Nanni Huser、William G. Rice、David M. Ryckman

  DOI：10.1021/ml300110s

  日期：2012.7.12

  Accelerated proliferation of solid tumor and hematologic cancer cells is linked to accelerated transcription of rDNA by the RNA polymerase I (Pol I) enzyme to produce elevated levels of rRNA (rRNA). Indeed, upregulation of Pol I, frequently caused by mutational alterations among tumor suppressors and oncogenes, is required for maintenance of the cancer phenotype and forms the basis for seeking selective inhibitors of Pot I as anticancer therapeutics. 2-(4-Methyl-[1,4]diazepan-1-yl)-5-oxo-5H-7-thia-1,11b-diaza-benzo[c]fluorene-6-carboxylic acid (5-methyl-pyrazin-2-ylmethyl)-amide (CX-5461, 7c) has been identified as the first potent, selective, and orally bioavailable inhibitor of RNA Pot I transcription with in vivo activity in tumor growth efficacy models. The preclinical data support the development of CX-5461 as an anticancer drug with potential for activity in several types of cancer.
• Pyridobenzothiazole derivatives as new chemotype targeting the HCV NS5B polymerase
  作者：Giuseppe Manfroni、Francesco Meschini、Maria Letizia Barreca、Pieter Leyssen、Alberta Samuele、Nunzio Iraci、Stefano Sabatini、Serena Massari、Giovanni Maga、Johan Neyts、Violetta Cecchetti

  DOI：10.1016/j.bmc.2011.11.061

  日期：2012.1

  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.