6-methoxy-2-(4'-fluorophenyl)-1,3-benzothiazole

• 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: 6-methoxy-2-(4'-fluorophenyl)-1,3-benzothiazole
• 英文别名: 2-(4-fluorophenyl)-6-methoxybenzo[d]thiazole；2-(4-fluorophenyl)-6-methoxy-1,3-benzothiazole；6-methoxy-2-(4'-fluorophenyl)benzothiazole；2-(4-fluorophenyl)-6-methoxybenzothiazole
• 化学式: C₁₄H₁₀FNOS
• 分子量: 259.304
• InChiKey: FFMONRZWRJLZNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methoxy-2-(4'-fluorophenyl)-1,3-benzothiazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到6-hydroxy-2-(4'-fluorophenyl)-1,3-benzothiazole
  参考文献：
  名称：

  Synthesis and Evaluation of ¹⁸F-Labeled 2-Phenylbenzothiazoles as Positron Emission Tomography Imaging Agents for Amyloid Plaques in Alzheimer’s Disease

  摘要：

  Imaging agents targeting amyloid beta(A beta) may be useful for early diagnosis and follow-up of treatment of patients with Alzheimer's disease (AD). Three of five tested 2-(4'-fluorophenyl)-1,3-benzothiazoles displayed high binding affinities for A beta plaques in AD human brain homogenates (K-i between 2.2 and 22.5 nM). They all contained the F-18-label directly attached to the aromatic ring and were synthesized starting from the nitro precursor. Determination of the partition coefficient, biodistribution studies in normal mice, and in vivo mu PET studies in normal rats showed that their initial brain uptake was high and brain washout was fast. The most promising compound [F-18]5, or 6- methyl-2-(4'-[F-18]fluorophenyl)-1,3-benzothiazole, seemed to be metabolically stable in the brain, and its plasma radiometabolites, which do not cross the blood-brain barrier, were determined. The preliminary results strongly suggest that this new fluorinated compound is a promising candidate as an A beta plaque imaging agent for the study of patients with AD.

  DOI：

  10.1021/jm8013376
• 作为产物：
  描述：

  2-氨基-6-甲氧基苯并噻唑 在 亚硝酸特丁酯 、 二氯双[二叔丁基-(4-二甲基氨基苯基)膦]钯(II) 、 四丁基溴化铵 、 caesium carbonate 、 对甲苯磺酸 、 copper(ll) bromide 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 13.0h， 生成 6-methoxy-2-(4'-fluorophenyl)-1,3-benzothiazole
  参考文献：
  名称：

  噻唑啉酮：多取代的苯并噻唑的通用中间体

  摘要：

  使用三甲基甲硅烷基甲基格氏试剂作为邻位碘代芳基三氟甲磺酸盐型前体的碘镁交换反应，可有效生成噻唑并苯并噻唑环。苯并噻唑环与噻唑环稠合。

  DOI：

  10.1039/c6cc05112j

文献信息

• Efficient 2-Aryl Benzothiazole Formation from Aryl Ketones and 2-Aminobenzenethiols under Metal-Free Conditions
  作者：Yunfeng Liao、Hongrui Qi、Shanping Chen、Pengcheng Jiang、Wang Zhou、Guo-Jun Deng

  DOI：10.1021/ol302902e

  日期：2012.12.7

  2-Aryl benzothiazole formation from aryl ketones and 2-aminobenzenethiols under metal- and I2-free conditions was described. Various 2-aryl benzothiazoles were selectively obtained in good yields using molecular oxygen as oxidant. DMSO played an important role in this transformation. Functional groups such as methyl, methoxy, fluoro, chloro, bromo and nitro groups were tolerated under the optimized reaction

  描述了在无金属和无I 2的条件下由芳基酮和2-氨基苯硫醇形成的2-芳基苯并噻唑。使用分子氧作为氧化剂，可以高收率选择性地获得各种2-芳基苯并噻唑。DMSO在此转型中发挥了重要作用。在优化的反应条件下，可以容忍甲基，甲氧基，氟，氯，溴和硝基等官能团。
• One-step synthesis of 2-arylbenzothiazole (‘BTA’) and -benzoxazole precursors for in vivo imaging of β-amyloid plaques
  作者：David Alagille、Ronald M. Baldwin、Gilles D. Tamagnan

  DOI：10.1016/j.tetlet.2004.12.111

  日期：2005.2

  We report the simple and efficient synthesis of 2-arylbenzothiazoles (‘BTA’) and 2-arylbenzoxazoles by direct coupling of benzothiazoles or benzoxazoles with aryl bromides. This method permits direct one-step access to precursors of radiolabeled BTA-1 and BTA-2 and their 6-methoxy analogues, used for in vivo imaging of β-amyloid plaques with positron emission tomography (PET).

  我们报告了通过苯并噻唑或苯并恶唑与芳基溴化物的直接偶联，简单而有效地合成了2-芳基苯并噻唑（'BTA'）和2-芳基苯并恶唑。这种方法允许直接一步访问放射性标记的BTA-1和BTA-2的前体及其6-甲氧基类似物，这些物质用于通过正电子发射断层扫描（PET）对β-淀粉样蛋白斑进行体内成像。
• Nucleophilic displacement method for synthesis of non-rigid PBZ polymers
  申请人：The Dow Chemical Company

  公开号：US05194562A1

  公开（公告）日：1993-03-16

  Azole rings, such as oxazole and thiazole rings, can activate an aromatic ring bonded to a leaving group such as a halogen atom so that the aromatic ring will undergo aromatic nucleophilic substitution. The reaction is useful for making ethers, thioethers and amines containing azole rings. In particular, monomers having azole rings, activated aromatic rings with leaving groups and nucleophilic moieties can react under conditions of aromatic nucleophilic displacement to form non-rigid rob PBZ polymers. The non-rigid rod PBZ polymers can be used to form molecular composites with rigid rod PBZ polymers which molecular composites are not substantially phase separated.

  唑环，如噁唑和噻唑环，可以激活与含卤原子等离子基团相结合的芳香环，从而使芳香环经历芳香亲核取代反应。该反应对于制备含有唑环的醚、硫醚和胺很有用。特别是，具有唑环、激活的含有离去基团的芳香环和亲核基团的单体可以在芳香亲核取代条件下反应，形成非刚性杆PBZ聚合物。非刚性杆PBZ聚合物可用于与刚性杆PBZ聚合物形成分子复合材料，这些分子复合材料基本上不会相分离。
• Monomers useful in nucleophilic displacement synthesis of polybenzazole
  申请人：The Dow Chemical Company

  公开号：US05216110A1

  公开（公告）日：1993-06-01

  Azole rings, such as oxazole and thiazole rings, can activate an aromatic ring bonded to a leaving group such as a halogen atom so that the aromatic ring will undergo aromatic nucleophilic substitution. The reaction is useful for making ethers, thioethers and amines containing azole rings. In particular, monomers having azole rings, activated aromatic rings with leaving groups and nucleophilic moieties can react under conditions of aromatic nucleophilic displacement to form non-rigid rod PBZ polymers. The non-rigid rod PBZ polymers can be used to form molecular composites with rigid rod PBZ polymers which molecular composites are not substantially phase separated.

  氮杂环类化合物，例如噁唑环和噻唑环，可以激活与卤素原子等离子基相连的芳香环，使得芳香环会经历芳香性亲核取代反应。该反应对于制备含有氮杂环的醚、硫醚和胺类化合物很有用。特别是，在芳香性亲核取代条件下，具有氮杂环、活化的含离去基的芳香环和亲核性官能团的单体可以反应，形成非刚性杆状PBZ聚合物。非刚性杆状PBZ聚合物可以用于与刚性杆状PBZ聚合物形成分子复合材料，这些分子复合材料没有明显的相分离。
• NUCLEOPHILIC FLUORINATION OF AROMATIC COMPOUNDS
  申请人：Satyamurthy Nagichettiar

  公开号：US20110178302A1

  公开（公告）日：2011-07-21

  Iodylbenzene derivatives substituted with electron donating as well as electron withdrawing groups on the aromatic ring are used as precursors in aromatic nucleophilic substitution reactions. The iodyl group (IO 2 ) is regiospecifically substituted by nucleophilic fluoride to provide the corresponding fluoroaryl derivatives. No-carrier-added [F-18]fluoride ion derived from anhydrous [F-18](F/Kryptofix, [F-18]CsF or a quaternary ammonium fluoride (e.g., Me 4 NF, Et 4 NF, n-Bu 4 NF, (PhCH 2 ) 4 NF) exclusively substitutes the iodyl moiety in these derivatives and provides high specific activity F-18 labeled fluoroaryl analogs. Iodyl derivatives of a benzothiazole analog and 6-iodyl-L-dopa derivatives have been synthesized as precursors and have been used in the preparation of no-carrier-added [F-18]fluorobenzothiazole as well as 6-[F-18]fluoro-L-dopa.

  取代了电子给予基团和电子吸引基团的碘苯衍生物在芳香族亲核取代反应中被用作前体。亚碘酰基团(IO2)被亲核氟以区域特异性取代，提供相应的氟芳基衍生物。无载体添加的[F-18]氟离子源自无水[F-18](F/Kryptofix、[F-18]CsF或季铵氟化物(例如Me4NF、Et4NF、n-Bu4NF、(PhCH2)4NF))，只取代这些衍生物中的亚碘酰基团，并提供高比活度的F-18标记的氟芳基类似物。苯并噻唑类似物和6-碘-L-多巴衍生物的亚碘衍生物已被合成为前体，并用于制备无载体添加的[F-18]氟苯并噻唑和6-[F-18]氟-L-多巴。