Durand-Niconoff J Sergio, Ortiz-Blanco Erik, Sosa-Ortiz Gabriela, Olivares-Romero José L, Juárez-Aguilar Enrique, Montoya-Hernández Eva Luz, Fernández-Pomares Cynthia, Tovar-Miranda Ricardo, Castro María Eugenia, Melendez Francisco J, Guerrero Tomás
Instituto de Ciencias Básicas, Universidad Veracruzana Dr. Luis Castelazo Ayala s/n, Col. Industrial Ánimas Xalapa Ver. 91190 Mexico
Universidad Veracruzana, Facultad de Bioanálisis Médicos s/n, U. H. Del Bosque Xalapa Ver. 91010 Mexico.
RSC Adv. 2021 Sep 22;11(50):31260-31271. doi: 10.1039/d1ra04611j. eCollection 2021 Sep 21.
The synthesis of six Mannich bases derived from hydroxycoumarins was carried out in moderate yields, two of these derivatives were described for the first time. Conformational analysis was performed through DFT theoretical calculations explaining the formation of stable six membered rings based on intramolecular hydrogen bonds within the structure. These findings were correlated with the antiproliferative activity. The biological activity of the Mannich bases through their antiproliferative activity in the HeLa cancer cell line is described for the first time, showing that the compounds were able to inhibit proliferation in cervical cancer by more than 60%. Likewise, the theoretical modeling of the photophysical properties was realized with promising results, showing that the HOMO-LUMO energies of the new compounds present the lowest electronic gap values for those with donor groups in their structure, which makes them potential fluorophores.
以中等产率合成了六种由羟基香豆素衍生的曼尼希碱，其中两种衍生物是首次被描述。通过密度泛函理论（DFT）计算进行构象分析，解释了基于结构内分子间氢键形成稳定六元环的过程。这些发现与抗增殖活性相关。首次描述了曼尼希碱通过其在HeLa癌细胞系中的抗增殖活性所表现出的生物活性，表明这些化合物能够抑制宫颈癌增殖超过60%。同样，光物理性质的理论建模也取得了有前景的结果，表明新化合物的最高占据分子轨道（HOMO）-最低未占据分子轨道（LUMO）能量对于结构中带有供体基团的化合物呈现出最低的电子能隙值，这使其成为潜在的荧光团。
