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Molecules 2018, 23(4), 875; doi:10.3390/molecules23040875

Facile Syntheses and Molecular-Docking of Novel Substituted 3,4-Dimethyl-1H-pyrrole-2-carboxamide/carbohydrazide Analogues with Antimicrobial and Antifungal Properties

1
School of Chemical Sciences, North Maharashtra University, Jalgaon 425001, India
2
Department of Biochemistry, Maharshi Dayanand University, Rohtak 124001, India
3
School of Medicine, Department of clinical & translational sciences, Creighton University, Omaha, NE 68178, USA
*
Authors to whom correspondence should be addressed.
Received: 3 March 2018 / Revised: 28 March 2018 / Accepted: 5 April 2018 / Published: 11 April 2018
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Abstract

The article describes the use of facile one-pot, high-yielding reactions to synthesize substituted 3,4-dimethyl-1H-pyrrole-2-carboxamides 3am and carbohydrazide analogues 5al as potential antifungal and antimicrobial agents. The structural identity and purity of the synthesized compounds were assigned based on appropriate spectroscopic techniques. Synthesized compounds were assessed in vitro for antifungal and antibacterial activity. The compounds 5h, 5i and 5j were found to be the most potent against Aspergillus fumigatus, with MIC values of 0.039 mg/mL. The compound 5f bearing a 2, 6-dichloro group on the phenyl ring was found to be the most active broad spectrum antibacterial agent with a MIC value of 0.039 mg/mL. The mode of action of the most promising antifungal compounds (one representative from each series; 3j and 5h) was established by their molecular docking with the active site of sterol 14α-demethylase. Molecular docking studies revealed a highly spontaneous binding ability of the tested compounds in the access channel away from catalytic heme iron of the enzyme, which suggested that the tested compounds inhibit this enzyme and would avoid heme iron-related deleterious side effects observed with many existing antifungal compounds. View Full-Text
Keywords: carboxamide; carbohydrazine; antibacterial; antifungal; molecular docking; Schiff base; NMR; IR carboxamide; carbohydrazine; antibacterial; antifungal; molecular docking; Schiff base; NMR; IR
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Bhosale, J.D.; Dabur, R.; Jadhav, G.P.; Bendre, R.S. Facile Syntheses and Molecular-Docking of Novel Substituted 3,4-Dimethyl-1H-pyrrole-2-carboxamide/carbohydrazide Analogues with Antimicrobial and Antifungal Properties. Molecules 2018, 23, 875.

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