Regiospecific Reduction of 4,6-Dinitrobenzimidazoles : Synthesis, Characterization, and Biological Evaluation

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Abouelhaoul, El Alami ; El Kihel, Abdellatif ; Ahbala, Mustapha ; Sdassi, Hamid ; Köhler, Leonhard ; Bauchat, Patrick ; Roisnel, Thierry ; Khan, Tariq A. ; Al Nasr, Ibrahim S. ; Koko, Waleed S. ; Schobert, Rainer ; Biersack, Bernhard:
Regiospecific Reduction of 4,6-Dinitrobenzimidazoles : Synthesis, Characterization, and Biological Evaluation.
In: Chemistry & Biodiversity. Bd. 20 (2023) Heft 7 . - e202300191.
ISSN 1612-1880
DOI: https://doi.org/10.1002/cbdv.202300191

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Abstract

Abstract The regiospecific reduction of 4,6-dinitrobenzimidazole derivatives leading to the corresponding 4-amino-6-nitrobenzimidazoles was studied. The identification of the formed product structures was accomplished by spectroscopic and X-ray diffraction data. The anticancer and antiparasitic activities of the synthesized compounds were examined, and promising activities against Toxoplasma gondii and Leishmania major parasites were discovered for certain 4,6-dinitrobenzimidazoles in addition to moderate anticancer activities of the 4-amino-6-nitrobenzimidazole derivatives against T. gondii cells. However, the tumor cell experiments revealed a promising sensitivity of p53-negative colon cancer cells to these compounds.