An efficient synthesis of rearranged new biologically active benzimidazoles derived from 2-formyl carvacrol

Bhoi, Rahul T.; Rajput, Jamatsing D.; Bendre, Ratnamala S.

doi:10.1007/s11164-021-04601-9

Cited by 5 publications

(1 citation statement)

References 31 publications

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“…Furthermore, the obtaining of derivatives related to the antiallergic drug astemizole 31 – 33 or lerisetron 34 , showed congeners with good IC 50 values, from 47 nM to 1.7 μM against NF54 and K1 strains; moreover, derivatives related to some natural products, as carvacrol, showed activity values of 0.48 – 1.76 μg/mL 35 . Ferroquine, a ferrocenyl-chloroquine in phase 2b studies, led to Baartzes et al to the obtaining and evaluation of ferrocenyl and neutral and cationic iridium (III) and rhodium (III) aminoquinoline-benzimidazole hybrids 36 , 37 and 2(2-pyridyl)benzimidazole 38 .…”

Section: Introductionmentioning

confidence: 99%

Antiplasmodial activity, structure–activity relationship and studies on the action of novel benzimidazole derivatives

Escala

Pineda

et al. 2023

Sci Rep

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Malaria cases and deaths keep being excessively high every year. Some inroads gained in the last two decades have been eroded especially due to the surge of resistance to most antimalarials. The search for new molecules that can replace the ones currently in use cannot stop. In this report, the synthesis of benzimidazole derivatives guided by structure–activity parameters is presented. Thirty-six molecules obtained are analyzed according to their activity against P. falciparum HB3 strain based on the type of substituent on rings A and B, their electron donor/withdrawing, as well as their dimension/spatial properties. There is a preference for electron donating groups on ring A, such as Me in position 5, or better, 5, 6-diMe. Ring B must be of the pyridine type such as picolinamide, other modifications are generally not favorable. Two molecules, 1 and 33 displayed antiplasmodial activity in the high nanomolar range against the chloroquine sensitive strain, with selectivity indexes above 10. Activity results of 1, 12 and 16 on a chloroquine resistance strain indicated an activity close to chloroquine for compound 1. Analysis of some of their effect on the parasites seem to suggest that 1 and 33 affect only the parasite and use a route other than interference with hemozoin biocrystallization, the route used by chloroquine and most antimalarials.

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