4-(1,3-Benzothiazol-2-yl)-3-(3-fluoropropoxy)aniline | 1240379-79-6

• 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: 4-(1,3-Benzothiazol-2-yl)-3-(3-fluoropropoxy)aniline
• CAS: 1240379-79-6
• 化学式: C₁₆H₁₅FN₂OS
• 分子量: 302.372
• InChiKey: OVTOYIZVGOJXCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  76.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-氟甲苯磺酸丙酯 、 5-氨基-2-(1,3-苯并噻唑-2-基)苯酚 在 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 12.0h， 以59.6%的产率得到4-(1,3-Benzothiazol-2-yl)-3-(3-fluoropropoxy)aniline
  参考文献：
  名称：

  Synthesis and evaluation of two fluorine-18 labelled phenylbenzothiazoles as potentialin vivotracers for amyloid plaque imaging

  摘要：

  Ltd. 2009年约翰·威利父子有限公司版权所有。

  DOI：

  10.1002/jlcr.1662

文献信息

• Synthesis and evaluation of two fluorine-18 labelled phenylbenzothiazoles as potential<i>in vivo</i>tracers for amyloid plaque imaging
  作者：K. Serdons、D. Vanderghinste、M. Van Eeckhoudt、P. Borghgraef、H. Kung、F. Van Leuven、T. de Groot、G. Bormans、A. Verbruggen

  DOI：10.1002/jlcr.1662

  日期：2009.9.15

  Uncharged derivatives of thioflavin-T have known in vitro and in vivo affinity for amyloid β. We synthesized and evaluated two derivatives with a fluorine-18 labelled fluoropropoxy substituent either at the 6-position or at the 2′-position of the 2-(4′-aminophenyl)-1,3-benzothiazole core with the aim to get suitable radiotracers to perform amyloid plaque imaging. The fluorine-18 labelled compounds were obtained by nucleophilic substitution of the corresponding tosyl precursors with [18F]fluoride with a radiochemical yield of 50%, yielding 6-(3′′-[18F]fluoropropoxy)-2-(4′-aminophenyl)-1,3-benzothiazole ([18F]2) and 2-[2′-(3′′-[18F]fluoropropoxy)-4′-aminophenyl]-1,3-benzothiazole ([18F]3) with a specific activity between 33 and 51 GBq/µmol. The identity of the radiolabelled compounds was confirmed using radio-LC-MS and by comparing retention times on RP-HPLC. Biodistribution studies in healthy mice showed for both compounds a relatively high initial brain uptake, which was significantly higher for [18F]2 than for [18F]3 (4.5% ID/g versus 3.0% ID/g, p<0.05). Wash-out from control brain was faster for [18F]3. In vitro binding affinity tests using human AD brain homogenates revealed that only compound 2 has affinity for fibrillar amyloid β (Ki=14.5 nM). This was confirmed by the incubation of transgenic APP mouse brain sections with the cold compounds, where 3 did not stain any structure whereas 2 stained amyloid plaques present in APP mouse brain. These data suggest that [18F]2 may be a useful tracer for in vivo visualization of fibrillar amyloid β. Copyright © 2009 John Wiley & Sons, Ltd.

  Ltd. 2009年约翰·威利父子有限公司版权所有。