| 1159301-90-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• CAS: 1159301-90-2
• 化学式: C₁₄H₁₀N₂O₄S
• 分子量: 302.31
• InChiKey: ZKDTVVKHJDOMEP-UHFFFAOYSA-N

物化性质

• 沸点：
  494.4±55.0 °C(predicted)
• 密度：
  1.468±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  85.49
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 copper diacetate 、 potassium carbonate 、 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 90.0h， 生成
  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：

  3-羟基-4-硝基苯甲醛 、 2-氨基-5-甲氧基苯硫酚 以 二甲基亚砜 为溶剂， 反应 31.0h， 以65%的产率得到
  参考文献：
  名称：

  Synthesis and β-amyloid binding properties of rhenium 2-phenylbenzothiazoles

  摘要：

  As a first step toward the development of (99m)Tc PiB analogs, we have synthesized six neutral Re 2-phenylbenzothiazoles via pendant or integrated approach. These Re compounds bind to A beta(1-40) fibrils with fairly good affinities (K(i) = 10.0-88.6 nM) and have moderate lipophilicities (logP(C18) = 1.21-3.26). The Re compounds prepared via the integrated approach are smaller in size, and therefore their corresponding 99mTc analogs would have a greater chance of crossing the blood-brain barrier well. For potential clinical applications, further optimization on the structure-activity relationship to obtain Re 2-phenylbenzothiazoles with higher binding affinities (< 10 nM) might be needed. The integrated approach reported here to obtain neutral, compact and lipophilic Re 2-phenylbenzothiazoles could to be applied to other high affinity pharmacophores as well as to generate (99m)Tc analogs that could hold promise for extending the use of Ab imaging in living human brain to many more clinical settings because they could be used with SPECT. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.096