6-Bromo-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-benzothiazole | 346691-90-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 6-Bromo-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-benzothiazole
• 英文别名: 6-Bromo-2-[4-(4-methylpiperazin-1-yl)phenyl]-1,3-benzothiazole
• CAS: 346691-90-5
• 化学式: C₁₈H₁₈BrN₃S
• 分子量: 388.331
• InChiKey: CLTHVXHFUZWNAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Bromo-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-benzothiazole 在 钯 三乙胺 、 sodium iodide 、 双氧水 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 生成 2-[4'-(4''-methylpiperazin-1-yl)phenyl]-6-[125]iodobenzothiazole
  参考文献：
  名称：

  Zhuang, Z. P.; Kung, M.-P.; Hou, C., Journal of labelled compounds and radiopharmaceuticals, 2001, vol. 44, p. S29 - S32

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(4-甲基哌嗪)苯甲醛 、 2-氨基-5-溴苯硫醇 以 二甲基亚砜 为溶剂， 生成 6-Bromo-2-[4-(4-methyl-piperazin-1-yl)-phenyl]-benzothiazole
  参考文献：
  名称：

  Zhuang, Z. P.; Kung, M.-P.; Hou, C., Journal of labelled compounds and radiopharmaceuticals, 2001, vol. 44, p. S29 - S32

  摘要：

  DOI：

文献信息

• Compounds and methods useful for rescuing cells from beta-amyloid toxicity and treatment of Alzheimer's disease
  申请人：Jin Lee-Way

  公开号：US20070254889A1

  公开（公告）日：2007-11-01

  The present invention is directed to pharmaceutical compositions comprising one or more compounds of Formulae I, II, III, IV, V, VI, VII, VIII, IX and X, or pharmaceutically acceptable salts thereof and excipients. The present invention provides a method of inhibiting β-amyloid plaque aggregation, the method comprising introducing into a mammal an aggregation-inhibiting amount of a compound of Formula I, II, III, IV, V, VI, VII, VIII, IX or X or a pharmaceutically acceptable salt, ester, amide or prodrug thereof. By inhibiting amyloid aggregation, this method is capable of rescuing cells that otherwise would be susceptible or further damaged by amyloidosis.

  本发明涉及一种制药组合物，包括式I、II、III、IV、V、VI、VII、VIII、IX和X中的一个或多个化合物，或其药学上可接受的盐和辅料。本发明提供了一种抑制β-淀粉样斑块聚集的方法，该方法包括向哺乳动物中引入式I、II、III、IV、V、VI、VII、VIII、IX或X中的一种化合物或其药学上可接受的盐、酯、酰胺或前药的抑制聚集量。通过抑制淀粉样聚集，该方法能够挽救那些本来易受淀粉样蛋白病损伤的细胞。
• Radioiodinated Styrylbenzenes and Thioflavins as Probes for Amyloid Aggregates
  作者：Z.-P. Zhuang、M.-P. Kung、C. Hou、D. M. Skovronsky、T. L. Gur、K. Plössl、J. Q. Trojanowski、V. M.-Y. Lee、H. F. Kung

  DOI：10.1021/jm010045q

  日期：2001.6.1

  We report for the first time that small molecule-based radiodiodinated ligands, showing selective binding to A beta aggregates, cross the intact blood-brain barrier by simple diffusion. Four novel ligands showing preferential labeling of amyloid aggregates of A beta (1-40) and A beta (1-42) peptides, commonly associated with plaques in the brain of people with Alzheimer's disease (AD), were developed. Two I-125-labeled styrylbenzenes, (E,E)-1-iodo-2,5-bis(3-hydroxycarbonyl-4-hydroxy)-styrylbenzene, 12 (ISB), and (E,E)-1-iodo-2,5-bis(3-hydroxycarbonyl-4-methoxy)styrylbenzene, 13 (IMSB), and two I-125-labeled thioflavins, 2-[4 '-(dimethylamino)phenyl]-6-iodobenzothiazole, 18a (TZDM), and 2- [4 '-(4 " -methylpiperazin-1-yl)phenyl]-6-iodobenzothiazole, 18b (TZPI), were prepared at a high specific activity (2200 Ci/mmol). In vitro binding studies of these ligands showed excellent binding affinities with K-d values of 0.08, 0.13, 0.06, and 0.13 nM for aggregates of A beta (1-40) and 0.15, 0.73, 0.14, and 0.15 nM for aggregates of A beta (1-42), respectively. Interestingly, under a competitive-binding assaying condition, different binding sites on A beta (1-40) and A beta (1-42) aggregates, which are mutually exclusive, were observed for styrylbenzenes and thioflavins. Autoradiography studies of postmortem brain sections of a patient with Down's syndrome known to contain primarily A beta (1-42) aggregates in the brain showed that both [I-125]18a and [I-125]18b labeled these brain sections, but [I-125]13, selective for A beta (1-40) aggregates, exhibited very low labeling of the comparable brain section. Biodistribution studies in normal mice after an iv injection showed that [I-125]18a and [I-125]18b exhibited excellent brain uptake and retention, the levels of which were much higher than those of [I-125]12 and [I-125]13. These findings strongly suggest that the new radioiodinated ligands, [I-125]12 (ISB), [I-125]13 (IMSB), [I-125]18a, (TZDM), and [I-125]18b (TZPI), may be useful as biomarkers for studying A beta (1-40) as well as A beta (1-42) aggregates of amyloidogenesis in AD patients.
• US7425318B2
  申请人：——

  公开号：US7425318B2

  公开（公告）日：2008-09-16
• USRE44338E1
  申请人：——

  公开号：USRE44338E1

  公开（公告）日：2013-07-02
• USRE44354E1
  申请人：——

  公开号：USRE44354E1

  公开（公告）日：2013-07-09