Synthesis of new bicarbazole-linked triazoles as noncytotoxic reactive oxygen species (ROS) inhibitors

Shazia Iqbal; Maria A. Khan; Zulqarnain Ansari; Almas Jabeen; Aisha Faheem; Saba Fazal-Ur-Rehman; Fatima Z. Basha

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Synthesis of new bicarbazole-linked triazoles as noncytotoxic reactive oxygen species (ROS) inhibitors

机译：作为非胞素毒性反应性氧（ROS）抑制剂的新双咔唑连接三唑的合成

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Carbazole analogs 3 and 4 and a new library of bicarbazole-linked triazoles 6-11 were prepared via new synthetic methodology. Metalcatalyzed oxidative coupling reaction was utilized for the synthesis of bicarbazole acetylene 4 and different metals (Zn~(+2), Co~(+2), Fe~(+3), Ni~(+2), Cu~(+2), Mn~(+2)) as catalyst were screened. Only Fe-catalyzed reaction was found to be excellent and gave homocoupled product 4. Cu-catalyzed 1,3-dipolar cycloaddition was also utilized to install triazole moiety for the synthesis of hybrid molecules 6-11. Based on reported anti-inflammatory activity of carbazole and triazole scaffolds, all compounds were screened for their reactive oxygen species (ROS) inhibitory potential. Results from these studies revealed triazole 9 as most active compound (IC_(50) value of 7.6 ± 0.1 mg/mL on human whole blood and 2.7 ± 0.09 mg/mL on isolated neutrophils) using ibuprofen as a standard. Therefore, class described herein can serve as attractive structural element for further studies on ROS inhibition.

机译：通过新的合成方法制备咔唑类似物3和4以及双咔唑连接三唑的新图书馆。金属催化氧化偶联反应用于合成双咔唑乙酰乙烯4和不同金属（Zn〜（+2），Co〜（+ 2），Fe〜（+ 3），Ni〜（+ 2），Cu〜（+2筛选催化剂的Mn〜（+2））。仅发现Fe催化的反应是优异的并且得到同耦合产物4. Cu催化的1,3-偶极环加法也用于安装三唑部分以合成杂化分子6-11。基于报道的咔唑和三唑支架的抗炎活性，筛选所有化合物，用于其活性氧（ROS）抑制潜力。这些研究的结果揭示了三唑9作为最活跃的化合物（IC_（50）的含量为7.6±0.1mg / ml，使用布洛芬作为标准使用布洛芬的27±0.09mg / ml。因此，本文描述的类可以用作有吸引力的结构元素，用于进一步研究ROS抑制。

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来源
《Synthetic Communications》 |2019年第20期|共12页
作者
Shazia Iqbal; Maria A. Khan; Zulqarnain Ansari; Almas Jabeen; Aisha Faheem; Saba Fazal-Ur-Rehman; Fatima Z. Basha;
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作者单位

H. E. J. Research Institute of Chemistry International Center for Chemical and Biological Sciences University of Karachi Karachi Pakistan;

H. E. J. Research Institute of Chemistry International Center for Chemical and Biological Sciences University of Karachi Karachi Pakistan;

Department of Chemistry University of Karachi Karachi Pakistan;

PCMD International Center for Chemical and Biological Sciences University of Karachi Karachi Pakistan;

PCMD International Center for Chemical and Biological Sciences University of Karachi Karachi Pakistan;

Department of Chemistry University of Karachi Karachi Pakistan;

H. E. J. Research Institute of Chemistry International Center for Chemical and Biological Sciences University of Karachi Karachi Pakistan;

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正文语种 eng
中图分类有机化学;
关键词
Carbazole; bicarbazole; triazoles; reactive oxygen species (ROS); oxidative stress;

机译：咔唑;双咔唑;三唑;反应性氧（ROS）;氧化应激;

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Synthesis of new bicarbazole-linked triazoles as noncytotoxic reactive oxygen species (ROS) inhibitors

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