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

TL;DR

This paper reports the synthesis of benzofurancarboxylate derivatives using microwave methods and evaluates their antimicrobial activity against various bacteria and fungi.

Contribution

The novel contribution is the microwave-assisted synthesis and identification of a highly active antimicrobial benzofurancarboxylate compound.

Findings

Methyl 5-bromo-7-[2-(N,N-diethylamino)ethoxy]-6-methoxy-2-benzofurancarboxylate hydrochloride showed significant antimicrobial activity.

The compound exhibited MIC values of 3–12 × 10−3 μmol/cm³ against Gram-positive bacteria and 9.4 × 10−2 μmol/cm³ against Candida and Aspergillus brasiliensis.

Molecular and crystal structures of a benzofurancarboxylate derivative were confirmed using single-crystal X-ray diffraction.

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/cm3
against Gram-positive bacteria; MIC
9.4 × 10−2 μmol/cm3
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.

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