(E)-2-(4-(4-(methylamino)styryl)phenyl)benzo[d]thiazol-6-ol | 1018070-82-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2-(4-(4-(methylamino)styryl)phenyl)benzo[d]thiazol-6-ol
• 英文别名: 2-[4-[(E)-2-[4-(methylamino)phenyl]ethenyl]phenyl]-1,3-benzothiazol-6-ol
• CAS: 1018070-82-0
• 化学式: C₂₂H₁₈N₂OS
• 分子量: 358.464
• InChiKey: SRUMDOLQIOQCSY-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  73.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-(4-(methylamino)styryl)phenyl)benzo[d]thiazol-6-ol 、 3-氟甲苯磺酸丙酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4-[(E)-2-[4-[6-(3-fluoropropoxy)-1,3-benzothiazol-2-yl]phenyl]ethenyl]-N-methylaniline
  参考文献：
  名称：

  Synthesis and evaluation of stilbenylbenzoxazole and stilbenylbenzothiazole derivatives for detecting β-amyloid fibrils

  摘要：

  This paper describes a novel series of stilbenylbenzoxazole ( SBO) and stilbenylbenzothiazole ( SBT) derivatives for beta- amyloid specific binding probes. These 24 compounds were synthesized and evaluated by competitive binding assay against beta- amyloid 1 - 42 ( A beta 42) aggregates using [I-125] TZDM. All the derivatives displayed higher binding affinities with K-i value in the subnanomolar range ( 0.10 - 0.74 nM) than Pittsburgh Compound- B ( PIB) ( 0.77 nM). Among these derivatives, SBT- 2, 5-. uoroethoxy- 2-{ 4-[ 2-( 4- methylaminophenyl) vinyl] phenyl} benzothiazole, showed lowest K-i value ( 0.10 nM). In conclusion, the preliminary results suggest that these compounds are implying a possibility as a probe for detection of A beta fibrils in Alzheimer's disease (AD) patients. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.004
• 作为产物：
  描述：

  4-[(E)-2-[4-(6-methoxy-1,3-benzothiazol-2-yl)phenyl]ethenyl]-N-methylaniline 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (E)-2-(4-(4-(methylamino)styryl)phenyl)benzo[d]thiazol-6-ol
  参考文献：
  名称：

  Synthesis and evaluation of stilbenylbenzoxazole and stilbenylbenzothiazole derivatives for detecting β-amyloid fibrils

  摘要：

  This paper describes a novel series of stilbenylbenzoxazole ( SBO) and stilbenylbenzothiazole ( SBT) derivatives for beta- amyloid specific binding probes. These 24 compounds were synthesized and evaluated by competitive binding assay against beta- amyloid 1 - 42 ( A beta 42) aggregates using [I-125] TZDM. All the derivatives displayed higher binding affinities with K-i value in the subnanomolar range ( 0.10 - 0.74 nM) than Pittsburgh Compound- B ( PIB) ( 0.77 nM). Among these derivatives, SBT- 2, 5-. uoroethoxy- 2-{ 4-[ 2-( 4- methylaminophenyl) vinyl] phenyl} benzothiazole, showed lowest K-i value ( 0.10 nM). In conclusion, the preliminary results suggest that these compounds are implying a possibility as a probe for detection of A beta fibrils in Alzheimer's disease (AD) patients. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.004

文献信息

• 타우 응집체에 높은 선택성을 가지는 화합물, 이를 포함하는 타우 표적 프로브, 및 이의 제조 방법
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY 한국과학기술연구원(319980077518) BRN ▼209-82-03522

  公开号：KR20190090448A

  公开（公告）日：2019-08-02

  본 발명은 타우 응집체에 우수한 결합력을 나타내어 치매를 포함한 퇴행성 뇌질환의 조기 진단과, 이의 예방 및 치료에 유용한 하기 화학식 1로 표시되는 화합물, 이의 제조 방법 및 이를 포함하는 약학적 조성물에 관한 것이다.

  这项发明涉及以下化合物及其制备方法和药学组合物，这些化合物用化学式1表示，具有优异的与tau凝聚体的结合力，对早期诊断、预防和治疗包括痴呆在内的退行性脑疾病非常有用。 化学式1:未提供
• LIGANDS FOR AGGREGATED TAU MOLECULES
  申请人：Kemp Steven John

  公开号：US20110171739A1

  公开（公告）日：2011-07-14

  Provided are certain benzothiazole, imidazothiazole, imidazopyrimidine and imidazopyridine compounds, including, for example: formula (I) and pharmaceutically and physiologically acceptable salts, hydrates, and solvates thereof. Such compounds can be used as diagnostic ligands or labels of tau protein and PHF.

  提供了某些苯并噻唑、咪唑噻唑、咪唑嘧啶和咪唑吡啶化合物，包括例如：式（I）和其药学和生理学上可接受的盐、水合物和溶剂化物。这些化合物可用作tau蛋白和PHF的诊断配体或标记。
• Ligands for aggregated tau molecules
  申请人：WisTa Laboratories Ltd.

  公开号：EP2338059B1

  公开（公告）日：2015-04-08
• US8895313B2
  申请人：——

  公开号：US8895313B2

  公开（公告）日：2014-11-25
• [EN] LIGANDS FOR AGGREGATED TAU MOLECULES<br/>[FR] LIGANDS POUR MOLÉCULES DE LA PROTÉINE TAU AGGLOMÉRÉES
  申请人：WISTA LAB LTD

  公开号：WO2010034982A1

  公开（公告）日：2010-04-01

  Provided are certain benzothiazole, imidazothiazole, imidazopyrimidine and imidazopyridine compounds, including, for example:formula (I) and pharmaceutically and physiologically acceptable salts, hydrates, and solvates thereof. Such compounds can be used as diagnostic ligands or labels of tau protein and PHF.