Synthesis of 4‐Hydroxycoumarin Heteroarylhybrids as Potential Antimicrobial Agents

Abstract

A new series of 4-hydroxycoumarin derivatives 3a-d was synthesized by the reaction of 3-bromo-4-hydroxy coumarin 1 with various heteroaldehydes 2a-d in good yields. The synthesized compounds were characterized on the basis of their elemental and spectral (IR, (1)H-NMR and mass spectrometry) analysis. All target compounds were evaluated for their in-vitro antimicrobial activity against Streptococcus pyogenes, methicillin-resistant Staphylococcus aureus, Pseudomonas aeruginosa, Klebsiella pneumonia, and Escherichia coli bacterial strains and fungal cultures of Candida albicans, Aspergillus fumigatus, Trichophyton mentagrophytes, and Penicillium marneffei by disk diffusion assay with slight modifications. The minimum inhibitory concentration (MIC) was determined for the test compounds as well as for reference standards. Among the tested compounds, 3a has shown the most potent antibacterial as well as antifungal activities.

Chemistry and application of 4-oxo-4H-1-benzopyran-3-carboxaldehyde

“…148 The compound 172 is also formed from 1 and 3-bromo-4-hydroxycoumarin (1:2 molar ratio) in MeOH-pyridine under reflux. 150 Shutov et al 151 have rectified their earlier report 152 …”

Synthesis and Chemical Reactivity of 4‐Oxo‐4H‐1‐benzopyran‐3‐carboxaldehyde

“…Several tertiary aromatic amines, methoxyphenols , and substituted indole , 3‐bromo‐4‐hydroxycoumarin condensed with 4‐oxo‐4 H ‐1‐benzopyran‐3‐carboxaldehyde 1 under acid catalysis or solvent free and catalyst free conditions or in methanol in the presence of pyridine to give 89 in moderate yield. The reaction with indole turned out to be very sensitive to the nature of R substituent (Scheme ).…”

The Influence of Methoxy and Ethoxy Groups on Supramolecular Arrangement of Two Methoxy-chalcones

“…[1][2][3][4][5][6][7][8][9] Chemically, the molecular skeleton is characterized by aromatic rings moieties connected through three-carbon bridge having a keto carbonyl group and one α,β-unsaturation ( Figure 1). 5,[10][11][12][13] Chalcones and chalcone derivatives are often obtained from natural or synthetic sources. 8,14 By synthesis perspective, the Claisen-Schmidt condensation of aromatic aldehyde and aromatic acetophenone under either base or acid catalysis is a widely employed method to the synthesis of chalcones.…”

“…8,14 By synthesis perspective, the Claisen-Schmidt condensation of aromatic aldehyde and aromatic acetophenone under either base or acid catalysis is a widely employed method to the synthesis of chalcones. 5,[10][11][12][13] The versatility of class is evident from its wide-ranging biological activities; in particular, antiviral, anthelmintic, amoebicidal, antibacterial, antiprotozoal, antiulcer, cytotoxic, insecticidal, and anticancer. 13,[15][16][17][18] Also, due to its chemical structure, several chalcones have been reported to exhibit non-linear optical (NLO) properties that turn these compounds into potential functional materials.…”