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Biphenylthiazole antibiotics with an oxadiazole linker: An approach to improve physicochemical properties and oral bioavailability.


ABSTRACT: A new series of oxadiazolylbiphenylthiazoles was prepared with the objective of improving the limited solubility of first-generation derivatives while maintaining antibacterial activity against drug-resistant Staphylococcus aureus. Studying the structure-activity relationship at the cationic part provided the piperazine-1-carboximidamide derivative 27 with a MIC (MRSA) value of 1.1 ?g/mL, bactericidal mode of action, and a 50-fold improvement in aqueous solubility. Additionally, 27 exhibited a wider safety margin against mammalian cells, and most importantly, a significant improvement in oral bioavailability.

SUBMITTER: Hagras M 

PROVIDER: S-EPMC5736435 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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Biphenylthiazole antibiotics with an oxadiazole linker: An approach to improve physicochemical properties and oral bioavailability.

Hagras Mohamed M   Hegazy Youssef A YA   Elkabbany Amr H AH   Mohammad Haroon H   Ghiaty Adel A   Abdelghany Tamer M TM   Seleem Mohamed N MN   Mayhoub Abdelrahman S AS  

European journal of medicinal chemistry 20171019


A new series of oxadiazolylbiphenylthiazoles was prepared with the objective of improving the limited solubility of first-generation derivatives while maintaining antibacterial activity against drug-resistant Staphylococcus aureus. Studying the structure-activity relationship at the cationic part provided the piperazine-1-carboximidamide derivative 27 with a MIC (MRSA) value of 1.1 μg/mL, bactericidal mode of action, and a 50-fold improvement in aqueous solubility. Additionally, 27 exhibited a w  ...[more]

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