2-(1H-苯并咪唑-2-基)喹啉-8-醇 | 1006589-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 2-(1H-苯并咪唑-2-基)喹啉-8-醇
• 英文名称: 2-(1H-benzo[d]imidazol-2-yl)quinolin-8-ol
• 英文别名: 2-(Benzimidazol-2-yl)quinolin-8-ol；2-(1H-benzimidazol-2-yl)quinolin-8-ol
• CAS: 1006589-82-7
• 化学式: C₁₆H₁₁N₃O
• 分子量: 261.283
• InChiKey: IDFFSQOLWRUEHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-苯并咪唑-2-基)喹啉-8-醇 、 zinc(II) chloride 以 二氯甲烷 为溶剂， 反应 36.0h， 以68%的产率得到2-(1H-benzoimidazol-2-yl)quinolin-8-ol zinc(II) dichloride
  参考文献：
  名称：

  Synthesis, structure and fluorescent properties of 2-(1H-benzoimidazol-2-yl)quinolin-8-ol ligands and their zinc complexes

  摘要：

  A series of 2-(1H-benzoimidazol-2-yl)quinolin-8-ol ligands (L1-L5) and their Zn(II) complexes (C1-C6) were synthesized and characterized by spectroscopic and elemental analyses. The molecular structures of C1 and C6 were confirmed by single-crystal X-ray diffraction; the zinc centre in complex C1 was found to be five-coordination as a distorted tetrahedral geometry, meanwhile the zinc centre in complex C6 adopted as six-coordination as a octahedral geometry. UV-Vis absorption and fluorescent spectra in different solvent were measured, and the substituent effects as well as those of the solvents on the luminescent properties were analyzed. The maximum emission wavelengths of all complexes were generally blue-shifted compared to the free ligands. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.09.012
• 作为产物：
  描述：

  在 sodium hydrogensulfite 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2-(1H-苯并咪唑-2-基)喹啉-8-醇
  参考文献：
  名称：

  2-芳基-1H-苯并[d]咪唑衍生物作为潜在微管靶向剂的合成与评价

  摘要：

  微管靶向剂（MTA）是抗癌药物发现的潜在候选药物。通过合成分子破坏微管形成或抑制解聚过程可以产生出色的抗癌候选药物。在这里，我们将 2,5-取代-1 H-苯并[d]咪唑衍生物作为潜在的秋水仙碱、诺考达唑结合位点靶向剂。使用温和的反应条件合成了大约 20 种苯并咪唑衍生物，收率 82.0%–94.0%。合成的化合物在三种细胞系中显示出中等至优异的抗癌活性，包括 Hela 细胞、A549 细胞、MRC-5 细胞。化合物B15、B16、B19和B20是三种不同细胞系中IC 50 <15 μM 的潜在候选者。在 MTT 测定中，化合物B15、B16、B19和B20显示出优异的抗增殖活性，使用 HeLa 和 A549 细胞系的 IC 50值在 5.3 ± 0.21 至 18.1 ± 0.32 μM 范围内。B15、B16、B19和B20的预测吸收、分布、代谢和排泄 (ADME) 特性和药物相似特性表

  DOI：

  10.1002/ddr.21909

文献信息

• 一种2-(1H-苯并[d]咪唑-2-基)-8-羟基喹啉的合成方法
  申请人：上海贤鼎生物科技有限公司

  公开号：CN110078707A

  公开（公告）日：2019-08-02

  本发明涉及有机合成技术领域，为解决现有2‑(1H‑苯并[d]咪唑‑2‑基)‑8‑羟基喹啉的合成方法产率低、会产生对环境有害物质的问题，提供了一种2‑(1H‑苯并[d]咪唑‑2‑基)‑8‑羟基喹啉的合成方法，将8‑羟基喹啉‑2‑甲醛和邻苯二胺溶于溶剂中，加入分子筛，搅拌并加热反应，反应完全后冷却至室温，加入乙酸乙酯稀释；所得有机相经水洗、干燥、过滤旋蒸、洗涤后，得到2‑(1H‑苯并[d]咪唑‑2‑基)‑8‑羟基喹啉。本发明反应体系不会产生对环境有害的物质，绿色环保，产率更高，对材料科学和分子生物学研究领域及其工业化发展具有重要意义。
• A fluorescent “ON–OFF–ON” switch for the selective and sequential detection of Hg²⁺and I⁻with applications in imaging using human AGS gastric cancer cells
  作者：Saswati Gharami、Krishnendu Aich、Paramita Ghosh、Lakshman Patra、Nabendu Murmu、Tapan K. Mondal

  DOI：10.1039/c9dt04245h

  日期：——

  A new fluorescent "on-off-on" probe (BIPQ) is designed and developed which selectively binds with Hg2+; its emission intensity is quenched almost 40-fold at 455 nm without interference from other metal cations. On gradual addition of I- to the solution of BIPQ-Hg2+, the emission reverts to its original intensity. The limits of detection of BIPQ for Hg2+ and I- are found to be on the order of 3.12 ×

  设计并开发了一种新型的荧光“ on-off-on”探针（BIPQ），该探针可选择性地与Hg2 +结合。其发射强度在455 nm处淬灭了近40倍，而不受其他金属阳离子的干扰。将I-逐渐添加到BIPQ-Hg2 +溶液中后，发射光恢复为原始强度。发现Hg2 +和I-的BIPQ的检出限分别为3.12×10-9和5.48×10-8 M的量级，这清楚地表明BIPQ可以在非常细微的水平上检测Hg2 +。用探针进行DFT和TDDFT研究，以建立理论和实验结果之间的相似性。最后，为了证明其在生物学领域的实际益处，使用BIPQ进行了活细胞成像实验，以检测人AGS胃癌细胞系中的Hg2 +。
• Synthesis and evaluation of <scp> 2‐aryl‐1 <i>H</i> </scp> ‐benzo[d]imidazole derivatives as potential microtubule targeting agents
  作者：Jung‐Seop Lee、In‐ho Song、Shrikant Dashrath Warkad、Gyu Seong Yeom、Pramod B. Shinde、Keum‐soo Song、Satish Balasaheb Nimse

  DOI：10.1002/ddr.21909

  日期：——

  Microtubule targeting agents (MTAs) are the potential drug candidates for anticancer drug discovery. Disrupting the microtubule formation or inhibiting the de-polymerization process by a synthetic molecule can lead to an excellent anticancer drug candidate. Here, we present the 2,5-substituted-1H-benzo[d]imidazole derivatives as potential colchicine, nocodazole binding site targeting agents. About

  微管靶向剂（MTA）是抗癌药物发现的潜在候选药物。通过合成分子破坏微管形成或抑制解聚过程可以产生出色的抗癌候选药物。在这里，我们将 2,5-取代-1 H-苯并[d]咪唑衍生物作为潜在的秋水仙碱、诺考达唑结合位点靶向剂。使用温和的反应条件合成了大约 20 种苯并咪唑衍生物，收率 82.0%–94.0%。合成的化合物在三种细胞系中显示出中等至优异的抗癌活性，包括 Hela 细胞、A549 细胞、MRC-5 细胞。化合物B15、B16、B19和B20是三种不同细胞系中IC 50 <15 μM 的潜在候选者。在 MTT 测定中，化合物B15、B16、B19和B20显示出优异的抗增殖活性，使用 HeLa 和 A549 细胞系的 IC 50值在 5.3 ± 0.21 至 18.1 ± 0.32 μM 范围内。B15、B16、B19和B20的预测吸收、分布、代谢和排泄 (ADME) 特性和药物相似特性表
• Synthesis, structure and fluorescent properties of 2-(1H-benzoimidazol-2-yl)quinolin-8-ol ligands and their zinc complexes
  作者：Juanjuan Xia、Zihong Zhou、Wen Li、Hu-Qin Zhang、Carl Redshaw、Wen-Hua Sun

  DOI：10.1016/j.ica.2012.09.012

  日期：2013.1

  A series of 2-(1H-benzoimidazol-2-yl)quinolin-8-ol ligands (L1-L5) and their Zn(II) complexes (C1-C6) were synthesized and characterized by spectroscopic and elemental analyses. The molecular structures of C1 and C6 were confirmed by single-crystal X-ray diffraction; the zinc centre in complex C1 was found to be five-coordination as a distorted tetrahedral geometry, meanwhile the zinc centre in complex C6 adopted as six-coordination as a octahedral geometry. UV-Vis absorption and fluorescent spectra in different solvent were measured, and the substituent effects as well as those of the solvents on the luminescent properties were analyzed. The maximum emission wavelengths of all complexes were generally blue-shifted compared to the free ligands. (C) 2012 Elsevier B. V. All rights reserved.