2-(2-(prop-2-yn-1-yloxy)phenyl)benzothiazole | 1396390-73-0

• 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: 2-(2-(prop-2-yn-1-yloxy)phenyl)benzothiazole
• 英文别名: 2-(2-(prop-2-ynyloxy)phenyl)benzo[d]thiazole；2-(2-(prop‑2-yn-1-yloxy)phenyl)benzo[d]thiazole；2-(2-Prop-2-ynoxyphenyl)-1,3-benzothiazole；2-(2-prop-2-ynoxyphenyl)-1,3-benzothiazole
• CAS: 1396390-73-0
• 化学式: C₁₆H₁₁NOS
• 分子量: 265.335
• InChiKey: SRILXSXGRYVAOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-(prop-2-yn-1-yloxy)phenyl)benzothiazole 在 copper(l) iodide 、 碳酸氢钠 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(4-((4-(5-((2-(benzo[d]thiazol-2-yl)phenoxy)methyl)isoxazol-3-yl)-2-methoxyphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-(4-(trifluoromethyl)phenyl)acetamide
  参考文献：
  名称：

  三唑和异恶唑标记的苯并噻唑/苯并恶唑衍生物作为有效的细胞毒剂的合成和生物学评估†

  摘要：

  癌症是人类的主要健康问题，也是最令人不安的疾病，在发达国家和发展中国家均会导致死亡。正确治疗该疾病仍然是一个挑战。化学疗法被认为是治愈该疾病的方法之一。在这项研究中，合成了一系列1,2,3-三唑和异恶唑连接的苯并噻唑/苯并恶唑衍生物，并评估了其对人癌细胞系（例如HeLa（宫颈）和A549（肺）细胞系）的抗癌活性。 ，以HEK-293细胞系为对照。其中，缀合物8a，8f，13g，13h和13j对人类癌细胞系显示出显着的细胞毒活性。此外，这些活性缀合物诱导与凋亡的内在途径有关的关键凋亡基因如caspase-9，caspase-3，BAX和细胞色素c的表达增加。这项研究可能为HeLa和肺癌细胞提供可能的抗癌疗法。

  DOI：

  10.1039/c8nj01249k
• 作为产物：
  描述：

  水杨醛 在 ammonium cerium (IV) nitrate 、 双氧水 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 2-(2-(prop-2-yn-1-yloxy)phenyl)benzothiazole
  参考文献：
  名称：

  Synthesis and biological evaluation of novel triazoles and isoxazoles linked 2-phenyl benzothiazole as potential anticancer agents

  摘要：

  A new series of isoxazoles and triazoles linked 2-phenyl benzothiazole were synthesized and evaluated for their anticancer activity. These compounds have been tested for their cytotoxicity against three cancer cell lines. Among the compounds tested, compound 5d showed good cytotoxicity against Colo-205 and A549 cells in comparison to standard control PMX 610(1). Further compound 5d has been tested for its apoptotic activity and its inhibitory activity against caspase and PARP proteins. Hence this compound has the potential that it can be selected for further biological studies. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.041

文献信息

• Silver(<scp>i</scp>)–organic frameworks assembled with flexible supramolecular synthons with a pendant ethynide arm attached to the heteroaryl skeleton
  作者：Bo Li、Ren-Wu Huang、Hong-Chang Yao、Shuang-Quan Zang、Thomas C. W. Mak

  DOI：10.1039/c3ce41752b

  日期：——

  flexible supramolecular synthons with a pendant ethynide arm attached to a heteroaryl skeleton and different silver(I) salts under solvent evaporation conditions yielded four silver–organic frameworks. In 1–4, the Ag7, Ag8 and Ag9 aggregates are fused together through trifluoroacetate groups and/or Ag–N coordination bonds to generate a 2D layer, and finally linked into 3D supramolecular networks by argentophilic

  在溶剂蒸发条件下，柔性超分子合成子与连接在杂芳基骨架上的乙炔悬垂臂和不同的银（I）盐的反应产生了四个银有机骨架。在1-4中，Ag 7，Ag 8和Ag 9聚集体通过三氟乙酸酯基团和/或Ag-N配位键融合在一起以生成2D层，最后通过亲银相互作用或氢键连接到3D超分子网络中。本结构的多样性也表明，溶剂和阴离子组分在银的组装中都起着至关重要的作用（I乙炔化物配合物。另外，已经在固态下研究了它们的发光行为。
• Triazole-Coupled Benzimidazole-Based Fluorescent Sensor for Silver, Bromide, and Chloride Ions in Aqueous Media
  作者：Yoon Gun Ko、Won Sik Na、Mayank、Narinder Singh、Doo Ok Jang

  DOI：10.1007/s10895-019-02407-y

  日期：2019.7

  oxygen binding sites was synthesized and its properties as a probe for cations were investigated. Probe S1 was found to be highly selective toward Ag+ ions in aqueous media. The fluorescence intensity of S1 was quenched as a function of the concentration of Ag+ ions in the presence of potential interfering cations with a detection limit of 2.70 μM. The resulting S1-Ag+ complex was subsequently studied for

  合成了具有氮和氧结合位点的三唑偶联苯并咪唑基荧光探针S1，并研究了其作为阳离子探针的性能。发现探针S1对水性介质中的Ag +离子具有高度选择性。在存在潜在干扰阳离子且检测限为2.70μM的情况下，S1的荧光强度根据Ag +离子的浓度而猝灭。得到的S1 -Ag +复合物随后研究了其阴离子识别能力和发现识别溴-和Cl -离子，揭示了浓度依赖性荧光增强，检测限分别为22.2和23.0μM。探针S1的荧光分布的恢复表明Ag +离子从S1- Ag +络合物中释放出来。探针S1是可以一手用于定性和定量测定的Ag的传感器+，溴-和Cl -在含水介质中的离子。
• Highly selective fluorescent probe for detection and visualization of palladium ions in mixed aqueous media
  作者：Manoj Kumar、Naresh Kumar、Vandana Bhalla

  DOI：10.1039/c2ra22869f

  日期：——

  A highly selective fluorescent probe based on hydroxyphenyl-benzothiazole is synthesized which shows palladium-mediated cleavage to produce fluorescence changes at two different wavelengths in mixed aqueous media.

  基于高选择性的荧光探针 羟苯基苯并噻唑 合成的化合物显示钯介导的裂解，在混合的水性介质中在两个不同的波长产生荧光变化。
• Synthesis and biological evaluation of novel triazoles and isoxazoles linked 2-phenyl benzothiazole as potential anticancer agents
  作者：Ravindra M. Kumbhare、Umesh B. Kosurkar、M. Janaki Ramaiah、Tulshiram L. Dadmal、S.N.C.V.L. Pushpavalli、Manika Pal-Bhadra

  DOI：10.1016/j.bmcl.2012.07.041

  日期：2012.9

  A new series of isoxazoles and triazoles linked 2-phenyl benzothiazole were synthesized and evaluated for their anticancer activity. These compounds have been tested for their cytotoxicity against three cancer cell lines. Among the compounds tested, compound 5d showed good cytotoxicity against Colo-205 and A549 cells in comparison to standard control PMX 610(1). Further compound 5d has been tested for its apoptotic activity and its inhibitory activity against caspase and PARP proteins. Hence this compound has the potential that it can be selected for further biological studies. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of triazole and isoxazole-tagged benzothiazole/benzoxazole derivatives as potent cytotoxic agents
  作者：Tulshiram L. Dadmal、K. Appalanaidu、Ravindra M. Kumbhare、Tanmoy Mondal、M. Janaki Ramaiah、Manika Pal Bhadra

  DOI：10.1039/c8nj01249k

  日期：——

  isoxazole-linked benzothiazole/benzoxazole derivatives were synthesized and evaluated for their anticancer activity against human cancer cell lines, such as HeLa (cervical), and A549 (lung) cell lines, with HEK-293 cell line used as a control. Among them, conjugates 8a, 8f, 13g, 13h and 13j displayed significant cytotoxic activity against human cancer cell lines. Furthermore, these active conjugates induced

  癌症是人类的主要健康问题，也是最令人不安的疾病，在发达国家和发展中国家均会导致死亡。正确治疗该疾病仍然是一个挑战。化学疗法被认为是治愈该疾病的方法之一。在这项研究中，合成了一系列1,2,3-三唑和异恶唑连接的苯并噻唑/苯并恶唑衍生物，并评估了其对人癌细胞系（例如HeLa（宫颈）和A549（肺）细胞系）的抗癌活性。 ，以HEK-293细胞系为对照。其中，缀合物8a，8f，13g，13h和13j对人类癌细胞系显示出显着的细胞毒活性。此外，这些活性缀合物诱导与凋亡的内在途径有关的关键凋亡基因如caspase-9，caspase-3，BAX和细胞色素c的表达增加。这项研究可能为HeLa和肺癌细胞提供可能的抗癌疗法。