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meso-Dihydroguaiaretic acid derivatives with antibacterial and antimycobacterial activity.

Abstract：

:Thirty-three meso-dihydroguaiaretic acid (meso-DGA) derivatives bearing esters, ethers, and amino-ethers were synthesized. All derivatives were tested against twelve drug-resistant clinical isolates of Gram-positive and Gram-negative bacteria, including sensitive (H37Rv) and multidrug-resistant Mycobacterium tuberculosis strains. Among the tested compounds, four esters (7, 11, 13, and 17), one ether (23), and three amino-ethers (30, 31, and 33) exhibited moderate activity against methicillin-resistant Staphylococcus aureus, whereas 30 and 31 showed better results than levofloxacin against vancomycin-resistant Enterococcus faecium. Additionally, nineteen meso-DGA derivatives displayed moderate to potent activity against M. tuberculosis H37Rv with minimum inhibitory concentration (MIC) values ranging from 3.125 to 50µg/mL. Seven meso-DGA derivatives bearing amino-ethers (26-31 and 33) exhibited the lowest MICs against M. tuberculosis H37Rv and G122 strains, with 31 being as potent as ethambutol (MICs of 3.125 and 6.25µg/mL). The presence of positively charged group precursors possessing steric and hydrophobic features (e.g. N-ethylpiperidine moieties in meso-31) resulted essential to significantly increase the antimycobacterial properties of parent meso-DGA as supported by the R-group pharmacophoric and field-based QSAR analyses. To investigate the safety profile of the antimycobacterial compounds, cytotoxicity on Vero cells was determined. The amino-ether 31 exhibited a selectivity index value of 23, which indicate it was more toxic to M. tuberculosis than to mammalian cells. Therefore, 31 can be considered as a promising antitubercular agent for further studies.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Reyes-Melo K,García A,Romo-Mancillas A,Garza-González E,Rivas-Galindo VM,Miranda LD,Vargas-Villarreal J,Favela-Hernández JMJ,Camacho-Corona MDR

doi

10.1016/j.bmc.2017.07.047

subject

Has Abstract

pub_date

2017-10-15 00:00:00

pages

5247-5259

issue

20

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(17)30334-6

journal_volume

25

pub_type

杂志文章

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