Synthesis and Investigation of Anthelmintic, Antibacterial and Antifungal Activity of 3,3-Diphenyl Propanamide Derivatives

Abstract

Objective: A novel series of substituted 3,3-diphenyl propanamide derivatives (I-VIII) were synthesized by reacting 3,3-diphenyl propanoyl chloride with different amines/amino acids, and all the derivatives were investigated for anthelmintic, antibacterial, and antifungal activity.Methods: All the compounds were characterized by infrared (IR) and1H- nuclear magnetic resonance spectrometry data. The synthesized derivatives were investigated for their anthelmintic activity employing housefly worms method and earthworm species model. The antibacterial and antifungal activity was performed employing cup plate method.Results: The synthesized compounds (VII and VIII) exhibited maximum anthelmintic activity as compared with standard drug albendazole at doses of 50 and 100 mg/mL, due to minimal paralyzing and death time in both housefly and earthworm models. The compounds (IV, VII, and VIII) at 50 μg/mL exhibited maximum activity against Gram-negative bacterial strains, namely, Escherichia coli, Pseudomonas aeruginosa as compared with ciprofloxacin and same compounds exhibited maximum antifungal activity against Candida albicans and Aspergillus niger in comparison with standard drug griseofulvin at 50 μg/mL.Conclusion: The synthesized compounds bearing amino acid moiety in their structure (VII-VIII) exhibited impressive anthelmintic activity in comparison with albendazole. This suggests that amino acid/peptide derivative of diphenyl propanamides can act as great anthelmintic agents. Further, the research can be performed to design potent antimicrobial diphenyl propanamide derivatives.

Impact of Solidago virgaurea Extract on Biofilm Formation for ESBL-Pseudomonas aeruginosa: An In Vitro Model Study

“…In another investigation conducted by Sachin Chaudhary (2019), it was observed that propenamide, when administered at a concentration of 50 µg/mL, demonstrated the highest level of efficacy against Gramnegative bacterial strains. Notably, these strains included Escherichia coli and Pseudomonas aeruginosa, outperforming the effects of ciprofloxacin [20]. Yasir et al (2017) reported that propenamide exhibited robust inhibition against Bacillus subtilis and Escherichia coli, displaying zone of inhibition measurements of 16 mm for both bacterial strains [21].…”

Lead Molecule Identification From Vitex Trifolia Linn for Helminthiasis Using in Vitro and in Silico Methods

“…Statistical analysis was performed by one-way analysis of variance (ANOVA) followed by Dunnett'st-test. At 95% confidence interval, p values<0.001 were considered significant [31].…”

“…The docking parameters used were as follows: GA population size = 100 and the maximum number of energy evaluation = 2,500,000, other parameters used were default values. The lowest binding energy conformation was searched out and used for further analysis [29][30][31].…”

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“…This is known for its use in the relief of arthritis pain. Long-term use of NSAIDs leads results in gastrointestinal ulceration, bleeding and nephrotoxicity 18,20 . The gastrointestinal damage is generally associated with two factors which include local irritation by carboxylic acid moiety, which is common in most NSAIDs (topical effect) and decreased the production of tissue prostaglandin (PGs), which minimizes the physiological role of cytoprotective prostaglandins in maintaining GI health and homeostasis 21 .…”

“…Studies showed that forming the derivative of the carboxylate function of representative NSAIDs resulted in an enhanced anti-inflammatory activity with reduced ulcerogenic effect. Moreover, certain compounds bearing 1, 3, 4-oxadiazole/thiadiazole and 1, 2, 4-triazole nucleus have been reported to bear significant anti-inflammatory activity 19,20 . In the last two decades, there has been a considerable amount of work in the role of reactive oxygen species in inflammation.…”