2-(4′-aminophenyl)-6-methoxymethoxybenzothiazole | 566170-03-4

• 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′-aminophenyl)-6-methoxymethoxybenzothiazole
• 英文别名: 2-(4'-aminophenyl)-6-methoxymethoxybenzothiazole；6-Momo-bta-0；4-[6-(methoxymethoxy)-1,3-benzothiazol-2-yl]aniline
• CAS: 566170-03-4
• 化学式: C₁₅H₁₄N₂O₂S
• 分子量: 286.354
• InChiKey: HFTAHZZDWXVEAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  85.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4′-aminophenyl)-6-methoxymethoxybenzothiazole 在 吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 乙腈 、 mineral oil 为溶剂， 反应 8.0h， 生成 C₁₉H₂₂N₂O₅S₂
  参考文献：
  名称：

  IMAGING METHOD FOR ACUTE LYMPHOBLASTIC LEUKEMIA USING AN IMAGING AGENT AND METHOD OF PRODUCING AN IMAGING AGENT

  摘要：

  本发明提供了一种体内成像方法，有助于早期诊断急性淋巴细胞白血病（ALL）。早期诊断特别有利于选择更积极的治疗方案，以估计在诊断时可视化ALL的成功率。

  公开号：

  US20190261858A1
• 作为产物：
  描述：

  6-甲氧基-2-(4-硝基苯基)苯并噻唑 在 sodium tetrahydroborate 、 copper diacetate 、 三溴化硼 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 25.0h， 生成 2-(4′-aminophenyl)-6-methoxymethoxybenzothiazole
  参考文献：
  名称：

  Synthesis and Evaluation of ¹¹C-Labeled 6-Substituted 2-Arylbenzothiazoles as Amyloid Imaging Agents

  摘要：

  The synthesis and evaluation of a series of neutral analogues of thioflavin-T (termed BTA's) with high affinities for aggregated amyloid and a wide range of lipophilicities are reported. Radiolabeling with high specific activity [C-11]methyl iodide provided derivatives for in vivo evaluation. Brain entry in control mice and baboons was high for nearly all of the analogues at early times after injection, but the clearance rate of radioactivity from brain tissue varied by more than 1 order of magnitude. Upon the basis of its rapid clearance from normal mouse and baboon brain tissues, [N-methyl-C-11]2-(4'-methylaminophenyl)-6-hydroxybenzothiazole (or [C-11]6-OH-BTA-1) was selected as the lead compound for further evaluation. The radiolabeled metabolites of [C-11]6-OH-BTA-1 were polar and did not enter brain. The binding affinities of [N-methyl-H-3]6-OH-BTA-1 for homogenates of postmortem AD frontal cortex and synthetic Abeta(1-40) fibrils, were similar (K-d = 1.4 nM and 4.7 nM, respectively), but the ligand-to-Abeta peptide binding stoichiometry was similar to400-fold higher for AD brain than Abeta(1-40) fibrils. Staining of AD frontal cortex tissue sections with 6-OH-BTA-1 indicated the selective binding of the compound to amyloid plaques and cerebrovascular amyloid. The encouraging in vitro and in vivo properties of [C-11]6-OH-BTA-1 support the choice of this derivative for further evaluation in human subject studies of brain Abeta deposition.

  DOI：

  10.1021/jm030026b

文献信息

• Novel Imaging Tracers for Early Detection and Treatment of Amyloid Plaques Caused by Alzheimer's Disease and Related Disorders
  申请人：Elmaleh David R.

  公开号：US20080267879A1

  公开（公告）日：2008-10-30

  The present invention relates to compounds and methods for imaging and treating Alzheimer's disease or an amyloidosis-associated pathological condition that utilize a novel amyloid imaging tracer for detecting amyloid deposits in a subject suffering from these conditions. In certain embodiments, the invention relates to [N-2[18F]fluoropropyl]-2-(4′-(methylamino)-phenyl)-6-hydroxybenzothiazole (F-18MHT) and dimers thereof.

  本发明涉及化合物和方法，用于成像和治疗阿尔茨海默病或与淀粉样蛋白病理状况相关的病理状况，利用一种新型的淀粉样成像示踪剂来检测患有这些病状的受试者体内的淀粉样沉积物。在某些实施例中，本发明涉及[N-2[18F]氟丙基]-2-(4′-(甲基氨基)-苯基)-6-羟基苯并噻唑(F-18MHT)及其二聚体。
• Crown ethers attenuate aggregation of amyloid beta of Alzheimer's disease
  作者：Yanli Tian、Xueli Zhang、Yuyan Li、Timothy M. Shoup、Xin Teng、David R. Elmaleh、Anna Moore、Chongzhao Ran

  DOI：10.1039/c4cc06029f

  日期：——

  Crown ethers were used to “neutralize” positive charges of the amino groups of Aβs through the formation of hydrogen bonds, and thus inhibit the aggregation of Aβs.

  冠醚被用来通过氢键的形成“中和”Aβ的氨基团的正电荷，从而抑制Aβ的聚集。
• AMYLOID IMAGING AS A SURROGATE MARKER FOR EFFICACY OF ANTI-AMYLOID THERAPIES
  申请人：UNIVERSITY OF PITTSBURGH - OF THE COMM

  公开号：US20130045164A1

  公开（公告）日：2013-02-21

  The present method for determining the efficacy of therapy in the treatment of amyloidosis involves administering to a patient in need thereof a compound of formula (I) or Formula (II) or structures 1-45 and imaging the patient. After said imaging, at least one anti-amyloid agent is administered to said patient. Then, an effective amount of a compound of formula (I) or Formula (II) or structures 1-45 is administered to the patient and the patient is imaged again. Finally, baseline levels of amyloid deposition in the patient before treatment with the anti-amyloid agent are compared with levels of amyloid deposition in the patient following treatment with the anti-amyloid agent.

  目前用于确定淀粉样变性治疗疗效的方法包括向需要治疗的患者施用式(I)或式(II)或结构1-45的化合物并对患者进行成像。在成像后，给予患者至少一种抗淀粉样蛋白药物。然后，向患者施用有效量的式(I)或式(II)或结构1-45的化合物，并再次对患者进行成像。最后，将抗淀粉样蛋白药物治疗前患者的淀粉样沉积基线水平与治疗后患者的淀粉样沉积水平进行比较。
• Synthesis and β-amyloid binding properties of rhenium 2-phenylbenzothiazoles
  作者：Kuo-Shyan Lin、Manik L. Debnath、Chester A. Mathis、William E. Klunk

  DOI：10.1016/j.bmcl.2009.02.096

  日期：2009.4

  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.
• US7270800B2
  申请人：——

  公开号：US7270800B2

  公开（公告）日：2007-09-18