点击化学法合成单芳氧基和双芳氧基连接的香豆素基三唑类化合物作为抗结核药物。
A click chemistry approach for the synthesis of mono and bis aryloxy linked coumarinyl triazoles as anti-tubercular agents.
机构信息
Department of Studies in Chemistry, Karnatak University, Pavate Nagar, Dharwad 580003, Karnataka, India.
Department of Studies in Chemistry, Karnatak University, Pavate Nagar, Dharwad 580003, Karnataka, India.
出版信息
Eur J Med Chem. 2015 Nov 13;105:194-207. doi: 10.1016/j.ejmech.2015.10.019. Epub 2015 Oct 22.
A series of mono and bis-triazole coumarin hybrids 6a-u and 9a-f respectively have been synthesized using 4-(azidomethyl)-2H-chromen-2-ones 5a-i and aryl propargyl ethers 2a-c/8 employing Click chemistry modified protocol for Azide-Alkyne cycloadditions(CuAAC). Anti-tubercular screening showed moderate activity for mono aryloxy compounds 6a-u with MIC 50-100 μg/mL, whereas the bis compounds 9a-f were more effective with MICs between 0.2 and 12.5 μg/mL. Molecular modeling and 3D-QSAR measurements using CoMFA and Topomer CoMFA further supported the observed results. The bis compound 9b showed excellent activity with MIC value as low as 0.2 μg/mL.
一系列的单和双三唑香豆素杂合体 6a-u 和 9a-f 分别通过使用 4-（叠氮甲基）-2H-色烯-2-酮 5a-i 和芳基丙炔基醚 2a-c/8 使用点击化学修饰的叠氮化物-炔烃环加成（CuAAC）协议合成。抗结核筛选显示单芳氧基化合物 6a-u 具有中等活性，MIC50-100μg/mL，而双化合物 9a-f 更有效，MIC 为 0.2-12.5μg/mL。使用 CoMFA 和 Topomer CoMFA 的分子建模和 3D-QSAR 测量进一步支持了观察到的结果。双化合物 9b 表现出优异的活性，MIC 值低至 0.2μg/mL。
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