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Microwave-assisted preparation and antimicrobial activity of O-alkylamino benzofurancarboxylates.

Ostrowska K, Hejchman E, Wolska I, Kruszewska H, Maciejewska D - Monatsh. Chem. (2013)

Bottom Line: Their in-vitro antimicrobial properties were assessed.Inhibition by the compounds of the growth of antibiotic-susceptible standards and clinically isolated strains of Gram-positive and Gram-negative bacteria, yeasts, and a human fungal pathogen was moderate to significant.The molecular and crystal structures of 2-(N,N-diethylamino)ethyl 6-acetyl-5-hydroxy-2-methyl-3-benzofurancarboxylate were established by single-crystal X-ray diffraction. .

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 1 Banacha, 02097 Warsaw, Poland.

ABSTRACT

Abstract: A series of derivatives of 2 and 3-benzofurancarboxylates were synthesized under microwave-assisted conditions. Their in-vitro antimicrobial properties were assessed. Inhibition by the compounds of the growth of antibiotic-susceptible standards and clinically isolated strains of Gram-positive and Gram-negative bacteria, yeasts, and a human fungal pathogen was moderate to significant. Methyl 5-bromo-7-[2-(N,N-diethylamino)ethoxy]-6-methoxy-2-benzofurancarboxylate hydrochloride was identified as the most active compound (MIC 3-12 × 10(-3) μmol/cm(3) against Gram-positive bacteria; MIC 9.4 × 10(-2) μmol/cm(3) against Candida and Aspergillus brasiliensis). The molecular and crystal structures of 2-(N,N-diethylamino)ethyl 6-acetyl-5-hydroxy-2-methyl-3-benzofurancarboxylate were established by single-crystal X-ray diffraction.

Graphical abstract: .

No MeSH data available.


Related in: MedlinePlus

Structures of 2 and 3-benzofurancarboxylic acids
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Related In: Results  -  Collection


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Fig1: Structures of 2 and 3-benzofurancarboxylic acids

Mentions: Our strategy was based on preparation of a series of derivatives of 2 and3-benzofurancarboxylic acids (Fig. 1). Acids1–6 were prepared as described elsewhere[15] and converted to their ammoniumsalts to improve solubility in polar solvents. Acids 1–4 and 6 were esterified withmethanol to protect the carboxyl group against O-alkylation.Fig. 1


Microwave-assisted preparation and antimicrobial activity of O-alkylamino benzofurancarboxylates.

Ostrowska K, Hejchman E, Wolska I, Kruszewska H, Maciejewska D - Monatsh. Chem. (2013)

Structures of 2 and 3-benzofurancarboxylic acids
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4495853&req=5

Fig1: Structures of 2 and 3-benzofurancarboxylic acids
Mentions: Our strategy was based on preparation of a series of derivatives of 2 and3-benzofurancarboxylic acids (Fig. 1). Acids1–6 were prepared as described elsewhere[15] and converted to their ammoniumsalts to improve solubility in polar solvents. Acids 1–4 and 6 were esterified withmethanol to protect the carboxyl group against O-alkylation.Fig. 1

Bottom Line: Their in-vitro antimicrobial properties were assessed.Inhibition by the compounds of the growth of antibiotic-susceptible standards and clinically isolated strains of Gram-positive and Gram-negative bacteria, yeasts, and a human fungal pathogen was moderate to significant.The molecular and crystal structures of 2-(N,N-diethylamino)ethyl 6-acetyl-5-hydroxy-2-methyl-3-benzofurancarboxylate were established by single-crystal X-ray diffraction. .

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 1 Banacha, 02097 Warsaw, Poland.

ABSTRACT

Abstract: A series of derivatives of 2 and 3-benzofurancarboxylates were synthesized under microwave-assisted conditions. Their in-vitro antimicrobial properties were assessed. Inhibition by the compounds of the growth of antibiotic-susceptible standards and clinically isolated strains of Gram-positive and Gram-negative bacteria, yeasts, and a human fungal pathogen was moderate to significant. Methyl 5-bromo-7-[2-(N,N-diethylamino)ethoxy]-6-methoxy-2-benzofurancarboxylate hydrochloride was identified as the most active compound (MIC 3-12 × 10(-3) μmol/cm(3) against Gram-positive bacteria; MIC 9.4 × 10(-2) μmol/cm(3) against Candida and Aspergillus brasiliensis). The molecular and crystal structures of 2-(N,N-diethylamino)ethyl 6-acetyl-5-hydroxy-2-methyl-3-benzofurancarboxylate were established by single-crystal X-ray diffraction.

Graphical abstract: .

No MeSH data available.


Related in: MedlinePlus