8-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)quinoline

• 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
• 英文名称: 8-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)quinoline
• 英文别名: 8-[(1-Benzyltriazol-4-yl)methoxy]quinoline；8-[(1-benzyltriazol-4-yl)methoxy]quinoline
• 化学式: C₁₉H₁₆N₄O
• 分子量: 316.362
• InChiKey: REGHRURJITVKIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  8-羟基喹啉 在 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 8-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)quinoline
  参考文献：
  名称：

  喹啉基1,2,3-三唑及其结构类似物对白色念珠菌生长和毒力特性的影响。

  摘要：

  白色念珠菌和其他一些非白色念珠菌物种一样，是一组酵母菌，会在人类中引起全身和表面的严重感染。尽管已经为发现新型抗真菌剂付出了巨大的努力，但在世界范围内，这些真菌感染的频率已急剧增加。为了寻求新的抗真菌化合物，我们事先合成并筛选了含有1,2,3-三唑（3a）作为有效念珠菌spp抑制剂的喹啉。在本研究中，已合成了3a的两个结构类似物（3b和3c）以确定喹啉的作用，并评估了它们的抗念珠菌活性。初步结果帮助我们确定3a和3b为铅抑制剂。化合物3a对C的IC50值。白色念珠菌ATCC 90028（标准）和白色念珠菌（耐氟康唑）菌株分别为0.044和2.3μg/ ml，而相同菌株的化合物3b给出的值为25.4和32.8μg/ ml。盘扩散，生长和时间杀灭曲线测定法显示在化合物3a和3b存在下对白色念珠菌的显着抑制。此外，3a具有杀菌性，而3b具有抑菌性。两种测试化合物均显着降低了蛋白酶和磷脂酶的分泌。

  DOI：

  10.1371/journal.pone.0175710

文献信息

• Synthesis, QSAR and anticandidal evaluation of 1,2,3-triazoles derived from naturally bioactive scaffolds
  作者：Mohammad Irfan、Babita Aneja、Umesh Yadava、Shabana I. Khan、Nikhat Manzoor、Constantin G. Daniliuc、Mohammad Abid

  DOI：10.1016/j.ejmech.2015.02.007

  日期：2015.3

  In the present study, we used eight natural precursors (1a-h) with most of them having promising antimicrobial activities and synthesised their novel 1,2,3-triazole derivatives (3a-h). In the reaction sequences, the precursor compounds (1a-h) were converted to their respective alkyne (2a-h) followed by addition of benzyl azide freshly prepared by the reaction of benzyl bromide with sodium azide using [3 + 2] azide-alkyne cycloaddition strategy. Structural elucidation of all the triazole derivatives was done using FT-IR, H-1, C-13 NMR, mass and elemental analysis techniques. The single crystal X-ray diffraction for 3d was also recorded. The result of in vitro anticandidal activity performed against three different strains of Candida showed that compound 3e was found superior/comparable to fluconazole (FLC) with IC50 values of 0.044 mu g/mL against Candida albicans (ATCC 90028), 12.022 mu g/mL against Candida glabrata (ATCC 90030), and 3.60 mu g/mL against Candida tropicalis (ATCC 750). Moreover, at their IC50 values, compounds 3e and 3h showed <5% hemolysis which indicates the non-toxic behaviour of these inhibitors. Cytotoxicity assay was also performed on VERO cell line and all the derivatives were found nontoxic up to the concentration of 10.0 mu g/mL. The in silico technique of 3D-QSAR was applied to establish structure activity relationship of the synthesized compounds. The results reveal the molecular fragments that play an essential role in improving the anticandidal activity. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Effect of quinoline based 1,2,3-triazole and its structural analogues on growth and virulence attributes of Candida albicans
  作者：Mohammad Irfan、Shadab Alam、Nikhat Manzoor、Mohammad Abid

  DOI：10.1371/journal.pone.0175710

  日期：——

  drastically worldwide. In our quest for the discovery of novel antifungal compounds, we had previously synthesized and screened quinoline containing 1,2,3-triazole (3a) as a potent Candida spp inhibitor. In the present study, two structural analogues of 3a (3b and 3c) have been synthesized to determine the role of quinoline and their anti-Candida activities have been evaluated. Preliminary results

  白色念珠菌和其他一些非白色念珠菌物种一样，是一组酵母菌，会在人类中引起全身和表面的严重感染。尽管已经为发现新型抗真菌剂付出了巨大的努力，但在世界范围内，这些真菌感染的频率已急剧增加。为了寻求新的抗真菌化合物，我们事先合成并筛选了含有1,2,3-三唑（3a）作为有效念珠菌spp抑制剂的喹啉。在本研究中，已合成了3a的两个结构类似物（3b和3c）以确定喹啉的作用，并评估了它们的抗念珠菌活性。初步结果帮助我们确定3a和3b为铅抑制剂。化合物3a对C的IC50值。白色念珠菌ATCC 90028（标准）和白色念珠菌（耐氟康唑）菌株分别为0.044和2.3μg/ ml，而相同菌株的化合物3b给出的值为25.4和32.8μg/ ml。盘扩散，生长和时间杀灭曲线测定法显示在化合物3a和3b存在下对白色念珠菌的显着抑制。此外，3a具有杀菌性，而3b具有抑菌性。两种测试化合物均显着降低了蛋白酶和磷脂酶的分泌。