1. Multicomponent synthesis and anti-proliferative screening of biaryl triazole-containing cyclophanes.
- Author
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Hernández-Vázquez E, Amador-Sánchez YA, Cruz-Mendoza MA, Ramírez-Apán MT, and Miranda LD
- Subjects
- Antineoplastic Agents pharmacology, Apoptosis drug effects, Biphenyl Compounds chemistry, Cell Line, Tumor, Cell Proliferation drug effects, Cycloaddition Reaction, Drug Screening Assays, Antitumor, Ethers, Cyclic pharmacology, Humans, Piperidines pharmacology, Structure-Activity Relationship, Antineoplastic Agents chemical synthesis, Ethers, Cyclic chemical synthesis, Piperidines chemical synthesis, Triazoles chemistry
- Abstract
We report a practical two-step approach involving a Ugi 4-CR/ azide-alkyne cycloaddition for the synthesis of biaryl-containing cyclophanes. The series represents an extension of our previously reported macrocycles as an effort to enhance the anti-proliferative activity of this scaffold. In this variant, we incorporate a biphenyl moiety in the framework, thus enhancing the macrocycle size, lipophilicity, and structural diversity. Macrocycles were tested against different cell lines, being more cytotoxic against prostate (PC-3 and DU-145) and breast (MCF-7) tumor cells. Gratifyingly, the most active compound showed a significative enhancement of PC-3 growth inhibition with respect to our previous series, reaffirming the potential anti-proliferative activity of this kind of cyclophanes., (Copyright © 2021 Elsevier Ltd. All rights reserved.)
- Published
- 2021
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