N-(3-methoxyphenyl)-4-nitrothiobenzamide | 247080-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-methoxyphenyl)-4-nitrothiobenzamide
• 英文别名: N-(3-methoxyphenyl)-4-nitrobenzene-1-carbothioamide；N-(3-methoxyphenyl)-4-nitrobenzenecarbothioamide
• CAS: 247080-14-4
• 化学式: C₁₄H₁₂N₂O₃S
• 分子量: 288.327
• InChiKey: OXXGARLJESEIHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-methoxyphenyl)-4-nitrothiobenzamide 在 sodium hydroxide 、 一氯化碘 、 溶剂黄146 、 tin(ll) chloride 、 potassium hexacyanoferrate(III) 作用下， 以 乙醇 为溶剂， 反应 6.5h， 生成 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 在 劳森试剂 作用下， 以 氯苯 为溶剂， 以64%的产率得到N-(3-methoxyphenyl)-4-nitrothiobenzamide
  参考文献：
  名称：

  2-（4-氨基苯基）苯并噻唑衍生物作为光敏剂的合成及生物学评价

  摘要：

  使用外源光敏剂的光动力疗法（PDT）目前已被批准用于治疗基底细胞癌（BCC）。2-（4-氨基苯基）苯并噻唑（6）由发色结构组成，可吸收UVA（315-400 nm）中的光。这些结果鼓励我们设计和合成各种2-苯基苯并噻唑（6）。在本文中研究了UVC激活的6在BCC细胞中诱导的光敏效应所涉及的凋亡机制。用6 -UVA处理的细胞显示出一些凋亡特征，包括亚G1群体的增加，膜联蛋白V结合的显着增加以及caspase-3的激活。6-UVA诱导线粒体膜电位（Δ降低ψ公吨），并通过增强的ROS产生和胞外信号调节激酶（ERK）和p38 MAPK表达的促进磷酸ATP。这些结果表明6- UVA在涉及ERK和p38活化的线粒体过程中引起光敏作用，并最终导致BCC细胞凋亡。

  DOI：

  10.1016/j.bmc.2010.04.082

文献信息

• SYNTHESIS OF 2-(4-AMINOPHENYL) BENZOTHIAZOLE DERIVATIVES AND USE THEREOF
  申请人：Wang Jeh-Jeng

  公开号：US20120215154A1

  公开（公告）日：2012-08-23

  The present invention provides a method of preparing a compound of formula 6 comprising: (a) reacting a compound of formula 1 with a compound of formula 2 to form a compound of formula 3 wherein X of formula 2 is Cl or OH; (b) treating the compound formula 3 with Lawesson's reagent to form a compound of formula 4 (c) reacting a compound of formula 4 with potassium ferricyanide to produce a compound of formula 5 and (d) performing catalytic reduction of nitro group of the compound of formula 5 with palladium on charcoal to generate the compound of formula 6, wherein R 1 of formulae 1-6 is H, C 1-10 alkyl, C 1-10 alkoxy or C 1-10 haloalkyl, and R 2 of formulae 1-6 is H or C 1-10 alkyl. The present invention also provides a photodynamic therapy to a patient having at least one tumor comprising the steps of: administering a compound of formula 6 (wherein R 1 and R 2 are defined as the above) in a pharmaceutically acceptable carrier to the patient; waiting for a sufficient time to allow the administered compound to be taken up by a target tissue having the at least one tumor; and irradiating a region of the patient containing the target tissue; wherein growth of the tumor is inhibited.

  本发明提供了一种制备6式化合物的方法，包括：(a) 将1式化合物与2式化合物反应以形成3式化合物，其中2式化合物的X为Cl或OH；(b) 用Lawesson试剂处理3式化合物以形成4式化合物；(c) 将4式化合物与氰化亚铁钾反应以生成5式化合物；(d) 用活性炭上的钯进行5式化合物的硝基团的催化还原，生成6式化合物，其中1-6式中的R1为H、C1-10烷基、C1-10烷氧基或C1-10卤代烷基，1-6式中的R2为H或C1-10烷基。本发明还提供了一种对患有至少一种肿瘤的患者进行光动力疗法的方法，包括以下步骤：向患者投药物学可接受的载体中的6式化合物（其中R1和R2如上所定义）；等待足够的时间以使给药的化合物被目标组织（至少一种肿瘤）吸收；照射患者身体含有目标组织的区域；从而抑制肿瘤的生长。
• 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。
• Metabolically Stabilized Benzothiazoles for Imaging of Amyloid Plaques
  作者：Gjermund Henriksen、Andrea I. Hauser、Andrew D. Westwell、Behrooz H. Yousefi、Markus Schwaiger、Alexander Drzezga、Hans-Jürgen Wester

  DOI：10.1021/jm061466g

  日期：2007.3.1

  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.
• Ligands for aggregated tau molecules
  申请人：WisTa Laboratories Ltd.

  公开号：EP2338059B1

  公开（公告）日：2015-04-08
• SYNTHESIS OF 2-(4-AMINOPHENYL)BENZOTHIAZOLE DERIVATIVES AND USE THEREOF
  申请人：KAOHSIUNG MEDICAL UNIVERSITY

  公开号：US20140046290A1

  公开（公告）日：2014-02-13

  The present invention provides a photodynamic therapy to a patient having at least one tumor comprising the steps of: administering a compound of formula 6 (wherein R 1 and R 2 are defined as the above) in a pharmaceutically acceptable carrier to the patient; waiting for a sufficient time to allow the administered compound to be taken up by a target tissue having the at least one tumor; and irradiating a region of the patient containing the target tissue, wherein growth of the tumor is inhibited.