N-(4'-bromophenyl)-4-nitrothiobenzamide | 566169-95-7

• 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-(4'-bromophenyl)-4-nitrothiobenzamide
• 英文别名: N-(4-bromophenyl)-4-nitrobenzenecarbothioamide
• CAS: 566169-95-7
• 化学式: C₁₃H₉BrN₂O₂S
• 分子量: 337.197
• InChiKey: WGGZOIGNWRNFBL-UHFFFAOYSA-N

物化性质

• 沸点：
  448.3±55.0 °C(Predicted)
• 密度：
  1.651±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4'-bromophenyl)-4-nitrothiobenzamide 在 sodium hydroxide 、 乙醇 、 potassium carbonate 、 tin(ll) chloride 、 potassium hexacyanoferrate(III) 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 18.0h， 生成 2-(4-methylaminophenyl)-6-bromobenzothiazole
  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
• 作为产物：
  描述：

  N-(4-溴苯基)-4-硝基苯甲酰胺 在 劳森试剂 、 hydroxymethylphospharamide 作用下， 生成 N-(4'-bromophenyl)-4-nitrothiobenzamide
  参考文献：
  名称：

  新型苯并[d]噻唑基取代-2-喹诺酮杂化物系列：设计、合成、生物学评价和计算机洞察

  摘要：

  摘要 3-(2-(4-(取代-苯并[d]噻唑-2-基)苯基氨基)乙酰基)-4-羟基-1-甲基/苯基喹啉-2(1H)-酮(7a -f 和 8a-f) 合成。适当取代的 2-(4-氨基苯基)苯并[d]噻唑 (4a-f) 与 3-(2-溴乙酰基)-4-羟基-1-甲基/苯基喹啉-2(1H)-one 的反应 ( 5/6) 在冰醋酸的存在下产生所需的化合物。合成化合物的结构基于它们的光谱（IR、1H NMR、13C NMR和MS）和元素分析来表征。细胞毒性筛选研究表明，MCF-7 和 WRL68 癌细胞对所有测试化合物均敏感。在 12 种新型杂交体中，化合物 8f 显示出最显着的抗癌活性。进行对接研究以了解标题化合物在目标酶（EGFR 酪氨酸激酶，1M17）活性位点的结合模式。化合物 8f 和 7f 显示出针对 1M17 的显着且保守的结合相互作用。此外，化合物 7e、7f、8e 和 8f 表现出有趣

  DOI：

  10.1016/j.molstruc.2020.129413

文献信息

• Synthesis and biological evaluation of thiobenzanilides as anticancer agents
  作者：Wan-Ping Hu、Hsin-Su Yu、Yan-Ren Chen、Yi-Min Tsai、Yin-Kai Chen、Chao-Cheng Liao、Long-Sen Chang、Jeh-Jeng Wang

  DOI：10.1016/j.bmc.2008.03.003

  日期：2008.5

  A series of novel thiobenzanilides is described. These compounds have been previously found to show strong biological activity such as antimycotic and antifungal actions. This is the first demonstration on the mechanism of the anticancer effect of thiobenzanilide agents (4a-c) on human melanoma A375 cells. The cytotoxic studies of compounds 4a-c on human melanoma A375 cells indicate thiobenzanilides induced higher cytotoxicity than nitrobenzanilides (3a-c). In addition, DNA flow cytometric analysis shows that 4a-c displays a significant G2/M phase arrest, which progresses to early apoptosis as detected by flow cytometry after double-staining with annexin V and propidium iodide (PI). Because cellular apoptosis is often preceded by the disruption of mitochondrial function, the assessment of mitochondrial function in 4a-c-treated cells is worthy of investigation. Our data revealed that treatment of A375 cells with 4a-c resulted in the loss of mitochondrial membrane potential (Delta Psi(mt)), a reduction of ATP synthesis, increased reactive oxygen species (ROS) generation, and activation of caspase-3. Thus, we suggest that 4a-c agents are potent inducers of cell apoptosis in A375 cells. (C) 2008 Elsevier Ltd. All rights reserved.
• Novel series of benzo[d]thiazolyl substituted-2-quinolone hybrids: Design, synthesis, biological evaluation and in-silico insights
  作者：Girish Bolakatti、Mahesh Palkar、Manjunatha Katagi、Girish Hampannavar、Rajshekhar V. Karpoormath、Shilpa Ninganagouda、Arvind Badiger

  DOI：10.1016/j.molstruc.2020.129413

  日期：2021.3

  Abstract A novel series of 3-(2-(4-(substituted-benzo[d]thiazol-2-yl)phenylamino)acetyl)-4‑hydroxy-1-methyl/phenyl quinolin-2(1H)-one (7a-f and 8a-f) were synthesized. Reaction of appropriately substituted-2-(4-amino phenyl)benzo[d]thiazole (4a-f) with 3-(2-bromoacetyl)-4‑hydroxy-1-methyl/phenyl quinolin-2(1H)-one (5/6) in the presence of glacial acetic acid resulted in desired compounds. Structures

  摘要 3-(2-(4-(取代-苯并[d]噻唑-2-基)苯基氨基)乙酰基)-4-羟基-1-甲基/苯基喹啉-2(1H)-酮(7a -f 和 8a-f) 合成。适当取代的 2-(4-氨基苯基)苯并[d]噻唑 (4a-f) 与 3-(2-溴乙酰基)-4-羟基-1-甲基/苯基喹啉-2(1H)-one 的反应 ( 5/6) 在冰醋酸的存在下产生所需的化合物。合成化合物的结构基于它们的光谱（IR、1H NMR、13C NMR和MS）和元素分析来表征。细胞毒性筛选研究表明，MCF-7 和 WRL68 癌细胞对所有测试化合物均敏感。在 12 种新型杂交体中，化合物 8f 显示出最显着的抗癌活性。进行对接研究以了解标题化合物在目标酶（EGFR 酪氨酸激酶，1M17）活性位点的结合模式。化合物 8f 和 7f 显示出针对 1M17 的显着且保守的结合相互作用。此外，化合物 7e、7f、8e 和 8f 表现出有趣
• Synthesis and Evaluation of ¹¹C-Labeled 6-Substituted 2-Arylbenzothiazoles as Amyloid Imaging Agents
  作者：Chester A. Mathis、Yanming Wang、Daniel P. Holt、Guo-Feng Huang、Manik L. Debnath、William E. Klunk

  DOI：10.1021/jm030026b

  日期：2003.6.1

  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.