4-((6-ethoxybenzothiazol-2-ylimino)methyl)phenol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 4-((6-ethoxybenzothiazol-2-ylimino)methyl)phenol
• 英文别名: 4-HBAEBT；4-[(6-Ethoxy-1,3-benzothiazol-2-yl)iminomethyl]phenol
• 化学式: C₁₆H₁₄N₂O₂S
• 分子量: 298.365
• InChiKey: BAOMWZMIJKEQBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  83
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-二氯-6-吗啉基-1,3,5-三嗪 、 4-((6-ethoxybenzothiazol-2-ylimino)methyl)phenol 在 potassium hydroxide 、 1-丁基-3-甲基咪唑二(三氟甲基磺酰)酰亚胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 12.0h， 以95%的产率得到(E)-N-(4-((4-chloro-6-morpholino-1,3,5-triazin-2-yl)oxy)benzylidene)-6-ethoxybenzo[d]thiazol-2-amine
  参考文献：
  名称：

  新型s-三嗪衍生物的合成，表征以及抗增殖和凋亡诱导作用†

  摘要：

  在试图设计和合成一类新的抗肿瘤剂的，用于亲核取代的温和和生态友好的协议使用š嗪骨架，通过胺和席夫碱衍生物，已被开发出来。为了获得抗肿瘤活性，在体外筛选所有合成的化合物对人纤维肉瘤肿瘤细胞（HT-1080）和宫颈癌细胞系（HeLa）的细胞毒性，以及它们抑制癌细胞生长的能力。选定的s -triazine类似物（5c，5d和6c）已针对HT-1080癌细胞系的活性氧（ROS）特性，线粒体膜电位（MMP）和凋亡（AO / EtBr）活性进行了初步研究。的体外抗癌活性分析表明，所合成的化合物具有针对所测试的细胞系好/中等抑制活性相对于标准药物。理论研究结果也提供了证据，表明通过基于结构的设计，s-三嗪支架已被成功鉴定为优越的p53-MDM2抑制剂。

  DOI：

  10.1039/c7nj03348f
• 作为产物：
  描述：

  对乙氧基苯胺 在 溴 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 20.0h， 生成 4-((6-ethoxybenzothiazol-2-ylimino)methyl)phenol
  参考文献：
  名称：

  基于3-羟基吡啶-4-酮和苯甲醛的部分苯并噻唑衍生物的合成及其对β-淀粉样蛋白聚集抑制作用的实验方法和分子动力学模拟评价

  摘要：

  一些基于(苯并[ d ]噻唑-2-基)-1-苯基甲胺衍生物的新型抑制剂被设计用于减少阿尔茨海默病的聚集过程。这些结构似乎模仿了二苯乙烯样支架，而苯并噻唑部分“锁定”了硫黄素 T 结合位点。其他抑制剂是基于2-((苯并[ d ]噻唑-2-基亚氨基)甲基)-5-(苄氧基)-1-甲基吡啶-4(H)-酮衍生物设计的。

  DOI：

  10.1002/cbdv.202301113

文献信息

• A green light emitting polymer in a PMMA matrix: oligo(azomethine-ether) \newlinewith benzothiazole moieties
  作者：Mehmet YILDIRIM、İsmet KAYA

  DOI：10.3906/kim-1405-66

  日期：——

  This study aimed to synthesize an oligo(azomethine-ether) with benzothiazole moiety in organic medium by means of chemical oxidative polycondensation (OP). Optical properties were examined by photoluminescence (PL) and UV-Vis measurements both in solutions and solid film involved a poly (methyl methacrylate) (PMMA) matrix. Oligomer film in the PMMA matrix emitted a fine green light with a fluorescence quantum yield (QY) of 3.30%. Spectral and thermal observations showed a high rate of C--O--C coupling (cross-linking) for the oligomer. SEC results indicated low molecular weight (\sim3200--4650 g mol^-1}) and the oligomer was soluble in organic solvents with high polarity. Electrochemical behavior was characterized by cyclic voltammetry (CV), morphological properties by scanning electron microscopy (SEM), and thermal characteristics by TG-DTA and DSC techniques.

  本研究旨在通过化学氧化缩聚（OP）的方法，在有机介质中合成具有苯并噻唑分子的寡聚（偶氮甲醚）。研究人员通过光致发光（PL）和紫外可见光（UV-Vis）测量法检测了溶液和涉及聚甲基丙烯酸甲酯（PMMA）基质的固体薄膜的光学特性。聚甲基丙烯酸甲酯（PMMA）基质中的低聚物薄膜发出细微的绿光，荧光量子产率（QY）为 3.30%。光谱和热观测结果表明，低聚物的 C-O-C 偶联（交联）速率很高。SEC 结果表明，低聚物的分子量较低（\sim3200--4650 g mol^-1}），并且可溶于极性较高的有机溶剂中。电化学行为采用循环伏安法（CV）进行表征，形态特性采用扫描电子显微镜（SEM）进行表征，热特性采用 TG-DTA 和 DSC 技术进行表征。
• Synthesis and biological evaluation of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases
  作者：Paola Vicini、Athina Geronikaki、Matteo Incerti、Bernadetta Busonera、Graziella Poni、Carla Alba Cabras、Paolo La Colla

  DOI：10.1016/s0968-0896(03)00493-0

  日期：2003.11

  Three new series of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases were synthesized and tested in vitro with the aim of identifying novel lead compounds active against emergent and re-emergent human and cattle infectious diseases (AIDS, hepatitis B and C, tuberculosis. bovine viral diarrhoea) or against drug-resistant cancers (leukaemia, carcinoma, melanoma, MDR tumors) for which no definitive cure or efficacious vaccine is available at present. In particular, these compounds were evaluated in vitro against representatives of different virus classes, such as a HIV-1 (Retrovirus), a HBV (Hepadnavirus) and the single-stranded RNA(+) viruses Yellow fever virus (YFV) and Bovine viral diarrhoea virus (BVDV), both belonging to Flaviviridae. Title compounds were also tested against representatives of Gram-positive and Gram-negative bacteria (Staphylococcus aureus, Salmonella spp.), various atypic mycobacterial strains Mycobacterium fortuitom and Mycobacterium smegmatis), yeast (Candida albicans) and mould (Aspergillus fumigatus). None of the compounds showed antiviral or antimicrobial activity. The benzo[ci]isothiazole compounds showed a marked Cytotoxicity (CC50 = 4-9 muM) against the human CD4(+) lymphocytes (MT-4) that were used to support HIV-1 growth. For this reason, the most cytotoxic compounds of this series were evaluated for their antiproliferative activity against a panel of human cell lines derived from haematological and solid tumors. The results highlighted that all the benzo[d]isothiazole derivatives inhibited the growth of leukaemia cell lines, whereas only one of the above mentioned compounds (1e) showed antiproliferative activity against two solid tumor-derived cell lines. (C) 2003 Elsevier Ltd. All rights reserved.
• New mesomorphic benzothiazol derivatives: Synthesis and characterization
  作者：Teck-Ming Koh、Sie-Tiong Ha、Guan-Yeow Yeap、Hong-Cheu Lin

  DOI：10.1016/j.cclet.2013.06.006

  日期：2013.10

  In this paper, the synthesis of new mesomorphic benzothiazolyl derivatives, 6-ethoxy-2-[4-(4-alkyloxybenzoyloxy)benzylidenamino]benzothiazoles, is presented. The structures of the title compounds were elucidated using spectroscopic techniques, such as FT-IR, NMR (H-1 and C-13), elemental analysis and EI-MS. The mesomorphic behaviours of these compounds were determined by differential scanning calorimetric and polarizing optical microscopic techniques. Compounds exhibited nematic and tilted smectic phases upon heating from crystal phase. An obvious odd-even effect was observed in this homologous series. (C) 2013 Sie-Tiong Ha. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Synthesis, characterization, and antiproliferative and apoptosis inducing effects of novel<i>s</i>-triazine derivatives
  作者：Mani Shanmugam、Kuppusamy Narayanan、Kamatam Hari Prasad、Dhanapalan Karthikeyan、Loganathan Chandrasekaran、Raji Atchudan、V. Chidambaranathan

  DOI：10.1039/c7nj03348f

  日期：——

  growth of cancer cells. The selected s-triazine analogs (5c, 5d, and 6c) have been preliminarily studied for their reactive oxygen species (ROS) properties, mitochondrial membrane potential (MMP) and apoptosis (AO/EtBr) activity against the HT-1080 cancer cell line. The in vitro anticancer activity analysis has revealed that the synthesized compounds have good/moderate inhibitory activity against the tested

  在试图设计和合成一类新的抗肿瘤剂的，用于亲核取代的温和和生态友好的协议使用š嗪骨架，通过胺和席夫碱衍生物，已被开发出来。为了获得抗肿瘤活性，在体外筛选所有合成的化合物对人纤维肉瘤肿瘤细胞（HT-1080）和宫颈癌细胞系（HeLa）的细胞毒性，以及它们抑制癌细胞生长的能力。选定的s -triazine类似物（5c，5d和6c）已针对HT-1080癌细胞系的活性氧（ROS）特性，线粒体膜电位（MMP）和凋亡（AO / EtBr）活性进行了初步研究。的体外抗癌活性分析表明，所合成的化合物具有针对所测试的细胞系好/中等抑制活性相对于标准药物。理论研究结果也提供了证据，表明通过基于结构的设计，s-三嗪支架已被成功鉴定为优越的p53-MDM2抑制剂。
• Synthesis of Some Benzothiazole Derivatives Based on 3‐Hydroxypyridine‐4‐one and Benzaldehyde and Evaluation of Their β‐Amyloid Aggregation Inhibition Using both Experimental Methods and Molecular Dynamic Simulation
  作者：Mohammad Hossein Asgarshamsi、Mehrdad Mohammadpour Dehkordi、Hossein Mohammad Beigi、Afshin Fassihi、Lotfollah Saghaie

  DOI：10.1002/cbdv.202301113

  日期：2023.10

  Some novel inhibitors based on the (benzo[d]thiazol-2-yl)-1-phenylmethanimine derivatives were designed to reduce the aggregation process in Alzheimer's disease. These structures seem to mimic stilbene-like scaffold, while the benzothiazole moiety “locks” the thioflavin T binding site. Other inhibitors were designed based on 2-((benzo[d]thiazol-2-ylimino)methyl)-5-(benzyloxy)-1-methylpyridin-4(H)-one

  一些基于(苯并[ d ]噻唑-2-基)-1-苯基甲胺衍生物的新型抑制剂被设计用于减少阿尔茨海默病的聚集过程。这些结构似乎模仿了二苯乙烯样支架，而苯并噻唑部分“锁定”了硫黄素 T 结合位点。其他抑制剂是基于2-((苯并[ d ]噻唑-2-基亚氨基)甲基)-5-(苄氧基)-1-甲基吡啶-4(H)-酮衍生物设计的。