N-(4-苯并噻唑-2-基-苯基)-乙酰胺 | 6265-57-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(4-苯并噻唑-2-基-苯基)-乙酰胺
• 英文名称: N-[4-(1,3-benzothiazol-2-yl)phenyl]acetamide
• 英文别名: N-(4-benzo[d]thiazol-2-yl phenyl)acetamide
• CAS: 6265-57-2
• 化学式: C₁₅H₁₂N₂OS
• 分子量: 268.339
• InChiKey: SMYRLHVRGXBMTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 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：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-苯并噻唑-2-基-苯基)-乙酰胺 在 劳森试剂 、 六甲基磷酰三胺 作用下， 反应 6.0h， 以61%的产率得到N-(4-Benzothiazol-2-yl-phenyl)-thioacetamide
  参考文献：
  名称：

  Antitumor Benzothiazoles. 7. Synthesis of 2-(4-Acylaminophenyl)benzothiazoles and Investigations into the Role of Acetylation in the Antitumor Activities of the Parent Amines

  摘要：

  2-(4-Aminophenyl)benzothiazoles display potent and selective antitumor activity against inter alia breast, ovarian, colon, and renal cell lines, but their mechanism of action, though yet to be defined, may be novel. Metabolism is suspected to play a central role in the mode of action of these benzothiazoles since drug uptake and biotransformation were observed in sensitive cell lines (e.g., breast MCF-7 and MDA 468 cells) in vitro, whereas insensitive cell lines (e.g., prostate PC 3 cells) showed negligible uptake and biotransformation. N-Acyl derivatives of the arylamines have been synthesized, and in vitro studies confirm N-acetylation and oxidation as the main metabolic transformations of 2-(4-aminophenyl)benzothiazoles, with the predominant process being dictated by the nature of the 3'-substituent. The prototype amine 3 underwent mainly N-acetylation in vitro, while 3'-substituted analogues 4 and 5 were primarily oxidized. N-Acetylation of 4 to 11 exerts a drastic dyschemotherapeutic effect in vitro, but acetylation of the halogeno congeners 5-7 gave acetylamines 12-14 which substantially retain selective antitumor activity. In vivo pharmacokinetic studies in rats confirmed rapid and exclusive N-acetylation of the 3'-methyl analogue 4, but less acetylation with the 3'-chloro analogue 5. Distinct expression patterns of N-acetyltransferase NAT1 and NAT2 have been demonstrated in our panel of cell lines.

  DOI：

  10.1021/jm981076x
• 作为产物：
  描述：

  4-(2-苯并噻唑基)苯胺 在 乙酸酐 作用下， 以 苯 为溶剂， 以88%的产率得到N-(4-苯并噻唑-2-基-苯基)-乙酰胺
  参考文献：
  名称：

  2-arylbenzazole compounds

  摘要：

  本文披露了含有3'-取代基和4'-NR.sup.2 R.sup.6取代基的2-苯基苯并咪唑化合物，其中苯基中的R.sup.5和R.sup.6分别为氢或烷基，或者4'-NR.sup.5 R.sup.6取代基为N-酰基（或N-苯甲酰基）。还披露了以4'-N磺酸盐形式存在的2-苯基苯并咪唑化合物。这些化合物在肿瘤细胞中表现出显著的选择性细胞毒活性，并为选择性治疗多种癌症提供了潜在有用的化疗药物。

  公开号：

  US06034246A1

文献信息

• 4-Acetamidobenzaldehyde Derivatives as Biological Active Candidates; Synthesis, Anti-oxidant, Anti-Alzheimer and DNA Binding Studies
  作者：Shahzad Murtaza、Adina Tatheer

  DOI：10.2174/1570180814666171026161646

  日期：2018.7.16

  Background: Due to high demand of developing new compounds to solve the health issues, paracetamol resembling 4-acetamidobenzaldehyde was derivatized into different new compounds including important pharmacophores (benzimidazole, benzothiazole). The synthesized compounds were investigated for anti-Alzheimer, antioxidant and DNA binding abilities. Methods: The new compounds were synthesized by the well-established synthetic routes. All synthesized compounds were analysed by H-NMR, 13C-NMR, Mass spectrometry and FTIR. Spectrophotometric method was applied for determination of inhibition potency against AChE and BChE. DPPH free radical scavenging method was used to check the antioxidant ability and the spectrophotometric titration was utilized to study the binding ability of synthesized derivatives with DNA. Results: 4-Acetamdiobenzaldehyde based derivatives were synthesized and characterised by HNMR, 13C-NMR, Mass spectrometry and FTIR. The synthesized compounds were analysed for anti-Alzheimer activity and results were compared by docking showed that 18 and 2 are good inhibitors of AChE and BChE. The results of DPPH radical scavenging activity explored most of the synthesized compounds as good antioxidants, out of these 18 showed maximum scavenging activities. Furthermore, compound 2 exhibited maximum intrinsic binding constant (K= 9.64×105M-1) for DNA. Conclusion: A new series of 4-Acetamidobenzaldehyde derivatives (1-20) were synthesized, characterized and studied for their antioxidant, anti-Alzheimer and DNA binding abilities. The results of anti-Alzheimer activity were compared by docking. Most of the synthesized compounds showed very significant antioxidants, anti-cholinesterase activities. All the compounds showed weak interaction with the DNA. These compounds are suitable for further pharmacological investigations.

  **背景：** 由于解决健康问题的新化合物开发需求高涨，与对乙酰氨基苯甲醛类似的4-乙酰氨基苯甲醛被衍生化为多种新型化合物，包括重要的药效团（苯并咪唑、苯并噻唑）。合成的化合物被研究其抗阿尔茨海默、抗氧化和DNA结合能力。 **方法：** 这些新型化合物通过成熟的合成路线被合成。所有合成的化合物均通过氢核磁共振（H-NMR）、碳13核磁共振（13C-NMR）、质谱（Mass spectrometry）和傅里叶变换红外光谱（FTIR）进行分析。光谱法用于测定对乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）的抑制效能。DPPH自由基清除法用于检验抗氧化能力，并使用光谱滴定法研究合成的衍生物与DNA的结合能力。 **结果：** 基于4-乙酰氨基苯甲醛的衍生物被合成并通过HNMR、13C-NMR、质谱和FTIR进行表征。这些合成的化合物被分析其抗阿尔茨海默活性，并通过对接模拟的结果对比显示，化合物18和2是AChE和BChE的良好抑制剂。DPPH自由基清除活性测试结果揭示大部分合成化合物具有良好的抗氧化性能，其中化合物18显示出最高的清除活性。此外，化合物2展现了最高的内在结合常数（K=9.64×10^5M^-1）与DNA结合。 **结论：** 一系列新的4-乙酰氨基苯甲醛衍生物（1-20）被合成、表征并研究了它们的抗氧化、抗阿尔茨海默和DNA结合能力。抗阿尔茨海默活性的结果通过对接模拟进行比较。大多数合成的化合物显示出非常显著的抗氧化和抗胆碱酯酶活性。所有化合物与DNA的相互作用较弱。这些化合物适合进行进一步的药理学研究。
• Novel Green Procedure for the Synthesis of 2-Arylbenzothiazoles Under Microwave Irradiation in Peg 200 Or Peg 400
  作者：Todor G. Deligeorgiev、Stefka Kaloyanova、Aleksey Vasilev、Juan J. Vaquero

  DOI：10.1080/10426501003598648

  日期：2010.10.28

  An improved green procedure for the synthesis of 2-aryl- and 2-hetarylbenzothiazoles by condensation of equivalent amounts of 2,2′-diaminodiphenyldisulfides or 2-aminothiophenols and various aromatic aldehydes in PEG 200/400 under microwave irradiation has been developed. This method allows the synthesis of 2-arylbenzothiazoles in high yields and with high purity regardless of the state of the starting

  已经开发了一种改进的绿色程序，用于通过在微波辐射下在 PEG 200/400 中缩合等量的 2,2'-二氨基二苯基二硫化物或 2-氨基苯硫酚和各种芳香醛来合成 2-芳基和 2-杂芳基苯并噻唑。无论起始化合物的状态（液体或固体）或芳环中取代基的性质如何，该方法都允许以高产率和高纯度合成 2-芳基苯并噻唑。
• Room temperature HFIP/Ag-promoted palladium-catalyzed C–H functionalization of benzothiazole with iodoarenes
  作者：Santosh Kori、Yuvraj Bhujbal、Kamlesh Vadagaonkar、Anant R. Kapdi、Saidurga Prasad Kommyreddy、Santosh J. Gharpure

  DOI：10.1039/d1cc06063e

  日期：——

  A versatile synthetic protocol involving the room temperature direct arylation of benzothiazole with a wide variety of iodoarenes under Ag-promoted Pd-catalyzed conditions in HFIP as the reaction solvent has been presented.

  一种多功能的合成方案，涉及在HFIP作为反应溶剂下，利用Ag促进的Pd催化条件下，将苯并噻唑与多种碘芳烃在室温下直接芳基化的方法。
• Ligand Combination Approach in Pd‐Catalyzed Direct C−H Arylation of Benzothiazole and Benzoxazole
  作者：Sneha Prasad Bakare、Mahendra Patil

  DOI：10.1002/ejoc.202301013

  日期：2024.1.8

  Two is better than one! A combination of two ligands (Phen.H2O and PPh3) with Pd catalyst offers a highly efficient catalytic system for the direct C−H arylation of benzothiazole and benzoxazole with aryl halides. Mechanistic studies including kinetic isotope effect experiments and computational investigations suggests that two ligands may work cooperatively to enhance the catalytic activity in the

  两个比一个好！两种配体（Phen.H 2 O和PPh 3）与Pd催化剂的组合为苯并噻唑和苯并恶唑与芳基卤化物的直接CH芳基化提供了高效的催化系统。包括动力学同位素效应实验和计算研究在内的机理研究表明，两个配体可能协同作用以增强反应中的催化活性。
• Brembilla,A.; Lochon,P., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1978, vol. 286, p. 557 - 559
  作者：Brembilla,A.、Lochon,P.

  DOI：——

  日期：——