Further and new target-based benzimidazole anthelmintics active against Teladorsagia circumcincta

Escala, Nerea; Valderas-García, Elora; Bardón, María Álvarez; Agüero, Verónica Castilla Gómez de; López-Pérez, Jose Luis; Rojo-Vázquez, F.A.; Feliciano, Arturo San; Martínez‐Valladares, María; Balaña‐Fouce, Rafael; Olmo, Esther del

doi:10.1016/j.molstruc.2022.133735

Cited by 8 publications

(17 citation statements)

References 33 publications

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“…To obtain the 2-arylcarbamidoBZ derivatives, the corresponding 2-amino-1 H -benzimidazole intermediate ( AI ) should be previously synthesized. The procedure to obtain AI 1–5 is indicated in a Escala et al previous work 40 . Here we indicate as an example compound AI-6 obtaining, solutions of the 4-nitro-1,2-phenylendiamine and cyanogen bromide in aqueous methanol (50% v/v) were prepared separately.…”

Section: Resultsmentioning

confidence: 99%

“…The obtaining process was the same as that described in Escala 40 ; solutions of 1.00 g (6.53 mmol) 4-nitro-1,2-phenylendiamine and cyanogen bromide 1.04 g (9.80 mmol) in aqueous methanol (50% v/v) were prepared separately. The solutions were then mixed in an Erlenmeyer flask and maintained with continuous magnetic stirring at room temperature for 48 h, obtaining 1.10 g (6.20 mmol) 95% 41 .…”

Section: Methodsmentioning

confidence: 99%

“…The protocol described in Escala et al 40 was applied. To a solution of the corresponding acid (1.3 mmol) in dry DMF (1 mL), DCI (1.3 mmol) was added, and the mixture maintained at room temperature for 1 h. Then, the corresponding 2-aminobenzimidazole intermediate (1.0 mmol) was added and the mixture maintained at room temperature with magnetic stirring for 16 h. The progress of the reaction was monitored by TLC using ethyl acetate as eluent.…”

Section: Methodsmentioning

confidence: 99%

“…BZs N -(5-methyl-1 H -benzimidazol-2-yl)picolinamide 1 , N -(5-chloro-1 H -benzimidazol-2-yl)picolinamide 12 were described in Escala 40 .…”

Section: Methodsmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…BZs N -(5-methyl-1 H -benzimidazol-2-yl)picolinamide 1 , N -(5-chloro-1 H -benzimidazol-2-yl)picolinamide 12 were described in Escala 40 .…”

Section: Methodsmentioning

confidence: 99%

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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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“…An urgent solution is required for the widespread issue of anthelmintic resistance to the primary medications used to treat helminth infections, particularly in ruminants [8]. The intensive use of anthelmintics to control gastrointestinal nematodes has become an essential issue in many countries, especially related to the problem of resistance [9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

Anthelmintic Resistance Status in Gastrointestinal Nematodes of Seven Different Breeds of Sheep in intensive management

Martindah¹,

Sawitri²,

Wardhana³

et al. 2023

IOP Conf. Ser.: Earth Environ. Sci.

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The severe use of anthelmintics to control gastrointestinal nematodes has become an essential issue in many countries, especially related to resistance issues. A study was carried out to determine the anthelmintic resistance status of intestinal nematodes of sheep, which were kept intensively in Bogor District, Indonesia. A total of 220 sheep of 7 breeds that routinely received Benzimidazole anthelmintics group to control gastrointestinal nematode were designated for this study. The animals were divided into 7 groups based on the breed and treated with Albendazole at the required dose. The Fecal Egg Count Reduction Test (FECRT) method was used to evaluate the anthelmintic’s effectiveness. The mean fecal egg count reduction was recorded at seven and fourteen days of treatment. The result indicated that 7 breeds of sheep were resistant to the anthelmintic used. Garut Local and Barbados Cross breeds showed relatively high resistance to Albendazole, with the mean fecal egg count at fourteen days of treatment being 60.24% and 67.97%, respectively. Haemonchus spp. larvae were the nematode larvae of strongyles species that grew the most in each breed of sheep from the fecal samples on day 0 (before treatment), day 7, and day 14 after treatment.

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Synthesis, Cytotoxic Activity, Docking and MD Simulation of N,N‐Disubstituted New Benzimidazolium Salts

Mavvaji,

Muhammed,

Akkoc

2023

ChemistrySelect

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Novel N,N‐disubstituted benzimidazolium salts were efficaciously synthesized in moderate to high yields and identified via 1H NMR and 13C NMR analyses. These compounds were tested on human liver cancer, prostate cancer, and normal embryonic kidney cell lines for 72 h. The results demonstrated that these compounds had antiproliferative activity. In particular, it was found that one of the compounds, 1‐(3‐chlorobenzyl)‐3‐(3‐methylbenzyl)‐1H‐benzo[d]imidazol‐3‐ium chloride, showed very high activity against liver cancer cell line and the IC50 value of this compound was almost twice as low as the IC50 value of cisplatin. The anticancer activity potential of the compounds was explored through computational methods to support the experimental study results. The binding potential of the compounds to human sulfotransferase 1A1 (SULT1A1) was investigated through molecular docking and molecular dynamics simulation. Their electrochemical properties were computed via density functional theory. The molecular docking study exhibited that 1‐(3‐methylbenzyl)‐3‐(4‐nitrobenzyl)‐1H‐benzo[d]imidazol‐3‐ium chloride had the highest potential to bind to SULT1A1. The molecular dynamics study showed that the synthesized compounds formed a stable complex. Furthermore, the density functional theory study exhibited that 1‐(3‐chlorobenzyl)‐3‐(4‐fluorobenzyl)‐1H‐benzo[d]imidazol‐3‐ium chloride might have the highest chemical stability.

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Further and new target-based benzimidazole anthelmintics active against Teladorsagia circumcincta

Cited by 8 publications

References 33 publications

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

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

Anthelmintic Resistance Status in Gastrointestinal Nematodes of Seven Different Breeds of Sheep in intensive management

Synthesis, Cytotoxic Activity, Docking and MD Simulation of N,N‐Disubstituted New Benzimidazolium Salts

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