Synthesis, Characterization, and Antimicrobial Evaluation of New N-Phenylcinnamamide Derivatives Linked to Aspirin and Ibuprofen

Abstract

Objective: The objective of this study was to synthesize phenylcinnamamide (substituted acetanilide chalcone) derivatives linked to aspirin and ibuprofen with potential antibacterial and antifungal activity.Methods: Substituted acetanilide compounds were reacted with different arylaldehydes through Claisen-Schmidt condensation in the presence of KOH. They formed differently substituted acetanilide chalcones (1a-e) which are linked to aspirin and ibuprofen through an ester linkage to form compounds (2a-j) using ethyl chloroformate (ECF) as a catalyst.Results: The synthesized compounds have been characterized by elemental analysis, Fourier transform infrared and1H-nuclear magnetic resonance spectroscopy. An antibacterial evaluation was achieved for Gram-positive bacteria (Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli) and antifungal for Candida albicans.Conclusion: Compounds (2a-j) have shown intermediate antimicrobial activity against different strains of microorganisms.

Aspirin Derivatives Exploration: A Review on Comparison Study with Parent Drug

“…Antimicrobial screening found that the compound 2c gave the highest inhibition against E. coli, 19 mm but 16 mm for the S. aureus, meanwhile 2a gave the highest inhibition of S. aureus, 18 mm, but against E. coli, 16 mm. As for the antifungal assay, 2c gave the largest inhibition of C. albicans, 18 mm, while 2a only gave 10 mm (79) . Although the aspirin with substituted amide (2a) has good antibacterial activity, the presence of -Cl substituent in the compound (2c) is slightly higher.…”

“…The synthesis of N-phenylcinnamamide derivatives that linked with aspirin (Scheme 6), started with dissolving the aryl aldehyde, giving substituted acetanilide chalcones compounds. The compounds were linked with aspirin by using mixed anhydride method, producing Nphenylcinnamamide-aspirin and continued with antimicrobial screening and antifungal assay (79) . The final product of aspirin-N-phenylcinnamamide had three phenyl rings but was able to inhibit S. aureus and E. coli.…”

“…Although the aspirin with substituted amide (2a) has good antibacterial activity, the presence of -Cl substituent in the compound (2c) is slightly higher. It was determined that its high lipophilicity which penetrated the bacterial cell wall has contributed to the higher success rate of inhibition (79) . This may caused by the lipophilic characteristic of N-phenylcinnamide due to interaction of its active site to the bacterial cell membrane and gain access to its target and restrained the bacteria (80,81) .…”

“…Aspirin-Amide Alwash et al (79) • Synthesis of Nphenylcinnamamide using Claisen-Schmidt condensation linked with aspirin, • In-vitro antibacterial and antifungal screening against E. coli, S. aureus and C. albicans…”

Synthesis and Characterization of Cyclohexane-1,3-Dione Derivatives and Their in Silico and in Vitro Studies on Antimicrobial and Breast Cancer Activity

“…Chalcone is a captivating moiety which consists of two aromatic rings linked by enone bridge and it belongs to the flavonoid family. Chalcones show various pharmacological activities such as anticancer, antiviral, antibacterial [7], and antifungal activity [8]. The C-C bond formation has been discovered in the past decades and its applications were reviewed [9][10][11][12][13][14].…”