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4-[5-methoxy-1,3-benzothiazol-2-yl]aniline | 162374-77-8

中文名称
——
中文别名
——
英文名称
4-[5-methoxy-1,3-benzothiazol-2-yl]aniline
英文别名
5-methoxy-2-(4-aminophenyl)-1,3-benzothiazole;4-(5-Methoxy-1,3-benzothiazol-2-yl)aniline
4-[5-methoxy-1,3-benzothiazol-2-yl]aniline化学式
CAS
162374-77-8
化学式
C14H12N2OS
mdl
——
分子量
256.328
InChiKey
URSIJLFKUGUAGH-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3.6
  • 重原子数:
    18
  • 可旋转键数:
    2
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.07
  • 拓扑面积:
    76.4
  • 氢给体数:
    1
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    4-[5-methoxy-1,3-benzothiazol-2-yl]aniline一氯化碘溶剂黄146 作用下, 反应 2.0h, 以34%的产率得到2-(4-amino-3-iodophenyl)-5-methoxybenzothiazole
    参考文献:
    名称:
    Antitumor Benzothiazoles. 8. Synthesis, Metabolic Formation, and Biological Properties of the C- and N-Oxidation Products of Antitumor 2-(4-Aminophenyl)benzothiazoles
    摘要:
    2-(4-Aminophenyl)benzothiazoles 1 and their N-acetylated forms have been converted to C- and N-hydroxylated derivatives to investigate the role of metabolic oxidation in the mode of action of this series of compounds. 2-(4-Amino-3-methylphenyl)benzothiazole (1a, DF 203, NSC 674495) is a novel and potent antitumor agent with selective growth inhibitory properties against human cancer cell lines. Very low IC50 values (<0.1 mu M) were encountered in the most sensitive breast cancer cell lines, MCF-7 and T-47D, whereas renal cell line TK-10 was weakly inhibited by la. Cell lines from the same tissue origin, MDA-MB-435 (breast), CAKI-1 (renal), and A498 (renal), were insensitive to 1a. Accumulation and metabolism of la were observed in sensitive cell lines only, with the highest rate of metabolism occurring in the most sensitive MCF-7 and T-47D cells. Thus, differential uptake and metabolism of 1a by cancer cell lines may underlie its selective profile of anticancer activity. A major metabolite in these sensitive cell lines has been identified as 2-(4-amino-3-methylphenyl)-6-hydroxybenzothiazole (6c). Hydroxylation of 1a was not detected in the homogenate of previously untreated MCF-7, T-47D, and TK-10 cells but was readily observed in homogenates of sensitive cells that were pretreated with 1a. Accumulation and covalent binding of [C-14]1a derived radioactivity was observed in the sensitive MCF-7 cell line but not in the insensitive MDA-MB-435 cell line. The mechanism of growth inhibition by 1a, which is unknown, may be dependent on the differential metabolism of the drug to an activated form by sensitive cell Lines only and its covalent binding to an intracellular protein. However, the 6-hydroxy derivative 6c is not the 'active' metabolite since, like all other C- and N-hydroxylated benzothiazoles examined in this study, it is devoid of antitumor properties in vitro.
    DOI:
    10.1021/jm990104o
  • 作为产物:
    描述:
    N-(3-methoxyphenyl)-4-nitrobenzamide劳森试剂sodium hydroxide 、 tin(ll) chloride 、 potassium hexacyanoferrate(III) 作用下, 以 六甲基磷酰三胺乙醇 为溶剂, 生成 4-[5-methoxy-1,3-benzothiazol-2-yl]aniline
    参考文献:
    名称:
    Metabolically Stabilized Benzothiazoles for Imaging of Amyloid Plaques
    摘要:
    Six new N-C-11-labeled aminophenylbenzothiazoles substituted with fluorine in different positions have been synthesized and evaluated as amyloid-beta binding ligands. Our structure-property relationship studies show that the substitution pattern of the phenyl ring and the benzothiazole moiety has an influence on the metabolic stability, which in turn has an effect on the brain uptake kinetics. Two lead compounds have been identified with improved physicochemical characteristics for A beta-plaque imaging in vivo.
    DOI:
    10.1021/jm061466g
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文献信息

  • 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。
  • 11C-labelled PIB analogues as potential tracer agents for in vivo imaging of amyloid β in Alzheimer's disease
    作者:K. Serdons、T. Verduyckt、D. Vanderghinste、P. Borghgraef、J. Cleynhens、F. Van Leuven、H. Kung、G. Bormans、A. Verbruggen
    DOI:10.1016/j.ejmech.2008.09.038
    日期:2009.4
    Pittsburgh Compound-B (PIB) is currently being evaluated clinically for in vivo visualization of amyloid plaques in patients with Alzheimer's disease (AD). We have synthesized three structural isomers of 6-hydroxy-2-(4'-aminophenyl)-1,3-benzothiazole, performed radiolabelling with carbon-11 and investigated their in vivo and in vitro properties. Specific binding to amyloid plaques was demonstrated in vitro using post-mortem brain homogenates of AD patients, transgenic AD mice brain sections and postmortem human AD brain sections. In normal mice, initial brain uptake (at 2 min p.i.) was high and was followed by a fast wash-out. The three structural analogues have a high potential as tracer agents for in vivo visualization of amyloid plaques in AD patients. (C) 2008 Elsevier Masson SAS. All rights reserved.
  • 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.
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