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Benzimidazole-1,2,3-triazole hybrid molecules: synthesis and evaluation for antibacterial/antifungal activity.

Ouahrouch A, Ighachane H, Taourirte M, Engels JW, Sedra MH, Lazrek HB - Arch. Pharm. (Weinheim) (2014)

Bottom Line: A novel series of hybrid molecules 4a-i and 5a-i were prepared by condensation of 4-(trimethylsilylethynyl)benzaldehyde 1 with substituted o-phenylenediamines.These in turn were reacted with 2-(azidomethoxy)ethyl acetate in a Cu alkyne-azide cycloaddition (CuAAC) to generate the 1,2,3-triazole pharmacophore under microwave assistance.The newly synthesized compounds were examined for their in vitro antimicrobial activities against Gram-positive and Gram-negative bacteria and the phytopathogenic fungi Verticillium dahliae and Fusarium oxysporum f. sp. albedinis. 2-((4-(4-(5-Trifluoromethyl benzimidazol-2-yl)phenyl)-1,2,3-triazol-1-yl)methoxy)ethanol 5e showed a moderate inhibition of 30% in the Foa sporulation test.

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Affiliation: Laboratory of Bioorganic and Macromolecular Chemistry, Department of Chemistry, Faculty of Sciences and Technology Gueliz (FSTG), Marrakesh, Morocco; Laboratory of Biomolecular and Medicinal Chemistry, Department of Chemistry, Faculty of Sciences Semlalia, Marrakesh, Morocco; Institute for Organic Chemistry and Chemical Biology, Goethe-University Frankfurt am Main, Frankfurt am Main, Germany.

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Comparison of the inhibition rate (%) of compounds 5a–h at the 8th day against VD and Foa at 20 µg/mL.
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fig02: Comparison of the inhibition rate (%) of compounds 5a–h at the 8th day against VD and Foa at 20 µg/mL.

Mentions: The result of the mycelia linear growth rate indicates that some of the compounds show a weak inhibition against the two fungi, the only compound that shows a significantly increased rate is compound 5e with (29.76%) (p < 0.05) against Verticillium dahliae ( Fig. 2). On the other hand, the sporulation was evaluated in the aim to know their fungicidal or fungistatic effect (Table 2, 3). The structure of this molecule uniquely holds a CF3 group fixed to the benzimidazole core. Since the trifluoromethyl group due to their lipophilicity is known to modulate absorption and metabolism, it may explain the enhanced activity.


Benzimidazole-1,2,3-triazole hybrid molecules: synthesis and evaluation for antibacterial/antifungal activity.

Ouahrouch A, Ighachane H, Taourirte M, Engels JW, Sedra MH, Lazrek HB - Arch. Pharm. (Weinheim) (2014)

Comparison of the inhibition rate (%) of compounds 5a–h at the 8th day against VD and Foa at 20 µg/mL.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4225497&req=5

fig02: Comparison of the inhibition rate (%) of compounds 5a–h at the 8th day against VD and Foa at 20 µg/mL.
Mentions: The result of the mycelia linear growth rate indicates that some of the compounds show a weak inhibition against the two fungi, the only compound that shows a significantly increased rate is compound 5e with (29.76%) (p < 0.05) against Verticillium dahliae ( Fig. 2). On the other hand, the sporulation was evaluated in the aim to know their fungicidal or fungistatic effect (Table 2, 3). The structure of this molecule uniquely holds a CF3 group fixed to the benzimidazole core. Since the trifluoromethyl group due to their lipophilicity is known to modulate absorption and metabolism, it may explain the enhanced activity.

Bottom Line: A novel series of hybrid molecules 4a-i and 5a-i were prepared by condensation of 4-(trimethylsilylethynyl)benzaldehyde 1 with substituted o-phenylenediamines.These in turn were reacted with 2-(azidomethoxy)ethyl acetate in a Cu alkyne-azide cycloaddition (CuAAC) to generate the 1,2,3-triazole pharmacophore under microwave assistance.The newly synthesized compounds were examined for their in vitro antimicrobial activities against Gram-positive and Gram-negative bacteria and the phytopathogenic fungi Verticillium dahliae and Fusarium oxysporum f. sp. albedinis. 2-((4-(4-(5-Trifluoromethyl benzimidazol-2-yl)phenyl)-1,2,3-triazol-1-yl)methoxy)ethanol 5e showed a moderate inhibition of 30% in the Foa sporulation test.

View Article: PubMed Central - PubMed

Affiliation: Laboratory of Bioorganic and Macromolecular Chemistry, Department of Chemistry, Faculty of Sciences and Technology Gueliz (FSTG), Marrakesh, Morocco; Laboratory of Biomolecular and Medicinal Chemistry, Department of Chemistry, Faculty of Sciences Semlalia, Marrakesh, Morocco; Institute for Organic Chemistry and Chemical Biology, Goethe-University Frankfurt am Main, Frankfurt am Main, Germany.

Show MeSH
Related in: MedlinePlus