A combination of two promising pharmacophore cores like
1,2,3-triazole (TA) and acetaminophen (APAP) in a single molecular entity could
be useful in the lead optimization step of drug research. Therefore, designing
and preparing new conjugated TA-APAP molecules is an important and actual task.
This book chapter describes an impressively efficient catalyzed Huisgen
reaction-based method for preparing a series of new 1-substituted
1,2,3-triazole-acetaminophen hybrids. The developed method, which does not require
chromatography column separation, is a practical and efficient solution. It
consists of the initial efficient O-propargylation reaction of APAP and
subsequent CuBr(PPh3)3-catalyzed [3+2] cycloaddition reaction between
O-propargylated APAP and diverse organoazides (R-N3) in the presence of
tert-BuOH: H2O (1:1) system. APAP was easily obtained from expired commercial
tablets using solid-liquid extraction as a starting material. An interesting
nitric oxide-releasing 1,2,3-triazole hybrid of APAP was also obtained
straightforwardly employing the developed method. These new drug hybrids were
obtained with good yields (64–93%). According to the in-silico ADME-Tox
assessment studies performed in this work and literature analysis, these
hybrids could be interesting models in search of new pharmacological nontoxic
agents endowed with anti-inflammatory and anticancer properties.
Author(s) Details:
Daniela Calderón Lamus,
Laboratorio de Química Orgánica y Biomolecular, Escuela de Química,
Universidad Industrial de Santander, A.A. 680002, Bucaramanga, Colombia.
Prof. Dr. Vladimir V. Kouznetsov
Laboratorio de Química Orgánica y Biomolecular, Escuela de Química, Universidad
Industrial de Santander, A.A. 680002, Bucaramanga, Colombia.
Please see the link here: https://stm.bookpi.org/CICMS-V9/article/view/14339
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