2-(4-methoxyphenyl)-6-nitrobenzothiazole | 53544-70-0

• 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-(4-methoxyphenyl)-6-nitrobenzothiazole
• 英文别名: 2-(4-Methoxyphenyl)-6-nitro-1,3-benzothiazole
• CAS: 53544-70-0
• 化学式: C₁₄H₁₀N₂O₃S
• 分子量: 286.311
• InChiKey: ZEJYOPOTUVODLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  96.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-6-nitrobenzothiazole 在 乙醇 、 potassium carbonate 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 2-chloro-N-[2-(4-methoxyphenyl)-1,3-benzothiazol-6-yl]acetamide
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship of rhenium 2-arylbenzothiazoles as β-amyloid plaque binding agents

  摘要：

  To continue our efforts toward the development of Tc-99m PiB analogs, we have synthesized 24 neutral and lipophilic Re (as a surrogate of Tc-99m) 2-arylbenzothiazoles, and explored their structure-activity relationship for binding to A beta(1-40) fibrils. These Re complexes were designed and synthesized via the integrated approach, so their 99mTc analogs would have a greater chance of crossing the blood-brain barrier. While the lipophilicities (logP(C18) = 1.59-3.53) of these Re 2-arylbenzothiazoles were all within suitable range, their binding affinities (K-i = 30-617 nM) to A beta(1-40) fibrils varied widely depending on the selection and integration of the tetradentate chelator into the 2-phenylbenzothiazole pharmacophore. For potential clinical applications, further refinement to obtain Re 2-arylbenzothiazoles with better binding affinities (<10 nM) will likely be needed. The integrated approach reported here to generate compact, neutral and lipophilic Re 2-arylbenzothiazoles could be applied to other potent pharmacophores as well to convert other current Ab PET tracers to their Tc-99m analogs for more widespread application via the use of SPECT scanners. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.068
• 作为产物：
  描述：

  2-氯-4-硝基苯胺 在 吡啶 、 tetraphosphorus decasulfide 、 sodium methylate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 2-(4-methoxyphenyl)-6-nitrobenzothiazole
  参考文献：
  名称：

  苯并咪唑和相关杂环作为拓扑异构酶I毒物的构效关系。

  摘要：

  合成了一系列取代的2-（4-甲氧基苯基）-1H-苯并咪唑类，并作为拓扑异构酶I的抑制剂进行了评估。存在5-甲酰基-，5-（氨基羰基）-或5-硝基（即取代基）能够充当氢键受体的分子）与选择的衍生物抑制拓扑异构酶I的潜力相关。与联苯并咪唑和叔苯并咪唑相反，作为拓扑异构酶I毒物具有活性的取代苯并咪唑显示出最低的DNA亲和力或没有DNA亲和力。5-硝基-2-（4-甲氧基苯基）-1H-苯并咪唑显示出最高的活性，并且比4-硝基位置异构体具有更高的活性。2-（4-甲氧基苯基）苯并恶唑，2-（4-甲氧基苯基）苯并噻唑的5-和6-硝基衍生物 合成了2-（4-甲氧基苯基）吲哚和2-（4-甲氧基苯基）吲哚，它们作为拓扑异构酶I抑制剂的相对活性。这些杂环类似物在DNA和拓扑异构酶I的存在下均不能有效地抑制可裂解复合物的形成，这表明与这些取代的苯并咪唑与酶或酶-DNA复合物的相互作用相关的高度结构特异性。在评估它们

  DOI：

  10.1016/0968-0896(96)00047-8

文献信息

• Practical Continuous-Flow Trapping Metalations of Functionalized Arenes and Heteroarenes Using TMPLi in the Presence of Mg, Zn, Cu, or La Halides
  作者：Matthias R. Becker、Paul Knochel

  DOI：10.1002/anie.201502393

  日期：2015.10.12

  The flow metalation of various arenes and heteroarenes involving an in situ trapping with metal salts (ZnCl2⋅2 LiCl, MgCl2, CuCN⋅2 LiCl, LaCl3⋅2 LiCl) under very convenient conditions (0 °C, 40 s) is reported. The resulting Mg, Zn, Cu, or La organic species are trapped with various electrophiles in high yields. In several cases, unusual kinetically controlled regioselectivities are obtained. All these

  各种芳烃和杂芳烃原位涉及一种用金属盐（氯化锌俘获的流动金属化2 ⋅2的LiCl，氯化镁2，CuCN⋅2的LiCl，的LaCl 3 ⋅2的LiCl）非常方便的条件下（0℃，40秒）是报告。生成的Mg，Zn，Cu或La有机物质被各种亲电试剂高产率捕集。在一些情况下，获得了异常的动力学控制的区域选择性。仅通过延长反应时间就可以按比例放大所有这些金属流，而无需进一步优化。这种流动金属化的反应范围比相应的分批程序的反应范围大得多。
• Iron(III)-Catalyzed Regioselective Synthesis of Electron-Rich Benzothiazoles from Aryl Isothiocyanates via C–H Functionalization
  作者：Bokka Srinivas、Kotari Shakeena、Durgeswari Lakkavarapu Kota、Valeti Abhinav、Pyla Eswar、Rongali Geetha Sravani、Anandam Sampath Pavan Kumar、Kiran Indukuri、Kumpatla Ayyappa Dhanaraju、Muthyala Murali Krishna Kumar、Santhosh Kumar Alla

  DOI：10.1021/acs.joc.2c03078

  日期：——

  for the preparation of 2-arylbenzothiazoles using aryl isothiocyanates and electron-rich arenes. The synthetic route involves triflic acid promoted addition of the arenes to aryl isothiocyanates followed by FeCl3-catalyzed C–S bond formation via C–H functionalization. The approach provides the advantage of synthesis of benzothiazoles without the conventional use of aryl aldehyde/carboxylic acid precursors

  我们在此报告了使用芳基异硫氰酸酯和富电子芳烃制备 2-芳基苯并噻唑的直接合成路线。合成路线包括三氟甲磺酸促进芳烃加成异硫氰酸芳基酯，然后通过C-H 官能化形成FeCl 3催化的 C-S 键。该方法提供了合成苯并噻唑的优势，而无需使用较便宜的铁 (III) 催化剂常规使用芳基醛/羧酸前体。
• Martvon,A. et al., Collection of Czechoslovak Chemical Communications, 1974, vol. 39, p. 1356 - 1365
  作者：Martvon,A. et al.

  DOI：——

  日期：——
• [DE] VERFAHREN ZUR HERSTELLUNG VON METALLIERTEN ORGANISCHEN VERBINDUNGEN<br/>[EN] METHODS FOR PRODUCING METALATED ORGANIC COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS ORGANIQUES MÉTALLÉS
  申请人：UNIV MUENCHEN LUDWIG MAXIMILIANS

  公开号：WO2016184652A9

  公开（公告）日：2017-08-10

  [EN] The present invention relates to methods for producing metalated organic compounds R1-Met under continuous flow conditions. The invention further relates to the metalated compounds obtained by these methods, and to the further reaction thereof with electrophilic reagents and the compounds obtained thereby. The invention also relates to methods for producing metalated organic compounds with Lewis-acidic hydrogen R1-Met using the base Cy2NLi.
  [FR] La présente invention concerne des procédés de production de composés organique métallés R1-Met dans des conditions de flux continu. Elle concerne également les composés métallés ainsi obtenus, ainsi que leur mise en réaction ultérieure avec des électrophiles et les composés ainsi obtenus. Elle concerne encore des procédés de production de composés organiques métallés avec de l'hydrogène d'acide de Lewis R1-Met à l'aide de la base Cy2NLi.
  [DE] Die vorliegende Anmeldung offenbart Verfahren zur Herstellung metallierter organischer Verbindungen R1-Met unter kontinuierlichen Flussbedingungen. Die Anmeldung offenbart auch die dadurch erhältlichen metallierten Verbindungen, sowie deren weitere Umsetzung mit Elektrophilen und die dadurch erhältlichen Verbindungen. Daneben werden Verfahren zur Herstellung metallierter organischer Verbindungen mit Lewis-acidem Wasserstoff R1-Met unter Verwendung der Base Cy2NLi offenbart.
• Design, synthesis and structure–activity relationship of rhenium 2-arylbenzothiazoles as β-amyloid plaque binding agents
  作者：Jinhe Pan、Neale S. Mason、Manik L. Debnath、Chester A. Mathis、William E. Klunk、Kuo-Shyan Lin

  DOI：10.1016/j.bmcl.2013.01.068

  日期：2013.3

  To continue our efforts toward the development of Tc-99m PiB analogs, we have synthesized 24 neutral and lipophilic Re (as a surrogate of Tc-99m) 2-arylbenzothiazoles, and explored their structure-activity relationship for binding to A beta(1-40) fibrils. These Re complexes were designed and synthesized via the integrated approach, so their 99mTc analogs would have a greater chance of crossing the blood-brain barrier. While the lipophilicities (logP(C18) = 1.59-3.53) of these Re 2-arylbenzothiazoles were all within suitable range, their binding affinities (K-i = 30-617 nM) to A beta(1-40) fibrils varied widely depending on the selection and integration of the tetradentate chelator into the 2-phenylbenzothiazole pharmacophore. For potential clinical applications, further refinement to obtain Re 2-arylbenzothiazoles with better binding affinities (<10 nM) will likely be needed. The integrated approach reported here to generate compact, neutral and lipophilic Re 2-arylbenzothiazoles could be applied to other potent pharmacophores as well to convert other current Ab PET tracers to their Tc-99m analogs for more widespread application via the use of SPECT scanners. (C) 2013 Elsevier Ltd. All rights reserved.