Cytotoxic Activity and Structure–Activity Relationship of Triazole‐Containing Bis(Aryl Ether) Macrocycles |
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| Authors: | Dr. Eduardo Hernández‐Vázquez Dr. Alejandra Chávez‐Riveros Dr. Adriana Romo‐Pérez María Teresa Ramírez‐Apán Dr. Alma D. Chávez‐Blanco Dr. Rocío Morales‐Bárcenas Dr. Alfonso Dueñas‐González Dr. Luis D. Miranda |
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| Affiliation: | 1. Department of Organic Chemistry, Instituto de Química, UNAM, Circuito Exterior S.N., Ciudad Universitaria, México, DF, México;2. Instituto Nacional de Cancerología, Tlalpan, Ciudad de México, CP, Mexico;3. Instituto de Investigaciones Biomédicas / Instituto Nacional de Cancerología, Tlalpan, Ciudad de México, CP, Mexico |
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| Abstract: | Cancer continues to be a worldwide health problem. Certain macrocyclic molecules have become attractive therapeutic alternatives for this disease because of their efficacy and, frequently, their novel mechanisms of action. Herein, we report the synthesis of a series of 20‐, 21‐, and 22‐membered macrocycles containing triazole and bis(aryl ether) moieties. The compounds were prepared by a multicomponent approach from readily available commercial substrates. Notably, some of the compounds displayed interesting cytotoxicity against cancer (PC‐3) and breast (MCF‐7) cell lines, especially those bearing an aliphatic or a trifluoromethyl substituent on the N‐phenyl moiety (IC50<13 μm ). Additionally, some of the compounds were able to induce apoptosis relative to the solvent control; in particular, (Z)‐N‐cyclohexyl‐7‐oxo‐6‐[4‐(trifluoromethyl)phenyl]‐11H‐3,10‐dioxa‐6‐aza‐1(4,1)‐triazola‐4(1,3),9(1,4)‐dibenzenacyclotridecaphane‐5‐carboxamide ( 12 f ) was the most potent in this regard (22.7 % of apoptosis). |
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| Keywords: | apoptosis cancer cytotoxicity macrocycles multicomponent reactions |
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