Potential antitumor agents. 59. Structure-activity relationships for 2-phenylbenzimidazole-4-carboxamides, a new class of "minimal" DNA-intercalating agents which may not act via topoisomerase II.

doi:10.1021/JM00164A054

Paper

Potential antitumor agents. 59. Structure-activity relationships for 2-phenylbenzimidazole-4-carboxamides, a new class of "minimal" DNA-intercalating agents which may not act via topoisomerase II.

Published Feb 1, 1990 · W. Denny, G. Rewcastle, B. Baguley

Journal of medicinal chemistry

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288

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0

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Abstract

A series of substituted 2-phenylbenzimidazole-4-carboxamides has been synthesized and evaluated for in vitro and in vivo antitumor activity. These compounds represent the logical conclusion to our search for "minimal" DNA-intercalating agents with the lowest possible DNA-binding constants. Such "2-1" tricyclic chromophores, of lower aromaticity than the structurally similar 2-phenylquinolines, have the lowest DNA binding affinity yet seen in the broad series of tricyclic carboxamide intercalating agents. Despite very low in vitro cytotoxicities, several of the compounds had moderate levels of in vivo antileukemic effects. However, the most interesting aspect of their biological activity was the lack of cross-resistance shown to an amsacrine-resistant P388 cell line, suggesting that these compounds may not express their cytotoxicity via interaction with topoisomerase II.

In Vitro Study

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Study Snapshot

2-phenylbenzimidazole-4-carboxamides show moderate in vivo antileukemic effects, with potential for non-topoisomerase II-mediated cytotoxicity.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Potential antitumor agents. 59. Structure-activity relationships for 2-phenylbenzimidazole-4-carboxamides, a new class of "minimal" DNA-intercalating agents which may not act via topoisomerase II.

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References

Citations

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Sustainable Synthesis of Benzimidazoles Catalyzed by Recyclable Functionalized Organosilica

This efficient method for benzimidazole synthesis using recyclable organosilica shows excellent catalyst activity and reusability for at least ten reaction cycles without significant activity loss.

Investigation of New Procedure for Selective Reaction and Synthesis of Some New 2-Substituted Benzimidazole Derivatives

NaBH4-FeCl2 effectively reduces NO2 groups on aromatic rings, yielding 90-95% desired products and successfully synthesising 2-substituted benzimidazole derivatives.

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The amide derivative 13a of 1,3,4-thiadiazole-benzimidazole shows potent anticancer activity against human breast, lung, colon, and ovarian cancers.

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C-3 functionalized imidazo[1,2-a]pyridine motifs offer new perspectives in heterocyclic chemistry and therapeutic molecule design.

Facile one pot synthesis of 2-substituted benzimidazole derivatives under mild conditions by using engineered MgO@DFNS as heterogeneous catalyst

Engineered MgO@DFNS is a sustainable catalyst for the synthesis of 2-substituted benzimidazole derivatives under mild conditions, offering eco-friendly, easy work-up, good selectivity, high yields, and quick recovery.

An Efficient Procedure for the Synthesis of 2-Arylsubstituted Benzimidazoles Catalyzed by Co (II) Immobilized on Fe3O4@SiO2-NH2/EP@SAA as a Recyclable Nanomagnetic Catalyst

This study presents a recyclable nanomagnetic catalyst for the efficient synthesis of 2-arylsubstituted benzimidazoles, offering a promising method for drug discovery.