SYNTHESIS OF SOME NOVEL (E)-METHYL 2,4-DIMETHYL-5-(3-OXO-3-PHENYLPROP-1-EN-1- YL)-1H-PYRROLE-3-CARBOXYLATE DERIVATIVES AS ANTIMICROBIAL AGENT

MAHESH HUBLIKAR; PRASHANT DIXIT; VIKAS KADU; SACHIN SHIRAME; DATTATRAYA RAUT; RAGHUNATH BHOSALE; SHRAVAN `JADHAV

doi:10.22159/ajpcr.2019.v12i2.30275

Authors

MAHESH HUBLIKAR Organic Chemistry Research Laboratory, School of Chemical Sciences, Solapur University, Solapur, Maharashtra, India.
PRASHANT DIXIT Department of Microbiology, Dr. Babasaheb Ambedkar Marathwada University, Sub Campus, Osmanabad, Maharashtra, India.
VIKAS KADU Organic Chemistry Research Laboratory, School of Chemical Sciences, Solapur University, Solapur, Maharashtra, India.
SACHIN SHIRAME Organic Chemistry Research Laboratory, School of Chemical Sciences, Solapur University, Solapur, Maharashtra, India.
DATTATRAYA RAUT Organic Chemistry Research Laboratory, School of Chemical Sciences, Solapur University, Solapur, Maharashtra, India.
RAGHUNATH BHOSALE Organic Chemistry Research Laboratory, School of Chemical Sciences, Solapur University, Solapur, Maharashtra, India.
SHRAVAN `JADHAV Department of Chemistry, DBF Dayanand College of Arts and Science, Solapur, Maharashtra, India.

DOI:

https://doi.org/10.22159/ajpcr.2019.v12i2.30275

Keywords:

Antimicrobial, Gram-positive, Gram-negative bacteria, Pyrrole chalcones

Abstract

Objective: The objective of the present study was to synthesize a series of some novel (E)-methyl 2,4-dimethyl-5-(3-oxo-3-phenylprop-1-en-1-yl)-1H-pyrrole-3-carboxylate derivatives and to evaluate it’s in vitro antimicrobial activities.

Methods: A novel series of (E)-methyl 2,4-dimethyl-5-(3-oxo-3-phenylprop-1-en-1-yl)-1H-pyrrole-3-carboxylate derivative (8a-l) has been synthesized by cyclization (Knorr reaction) hydrolysis, decarboxylation, and Vilsmeier–Haack formylation reaction. 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate 6 undergo condensation with acetophenone derivatives 7a-l in methanol and potassium hydroxide. The synthesized compounds were screened for in vitro antimicrobial screening.

Results: The structures of the synthesized compounds were characterized by infrared, 1H nuclear magnetic resonance, and mass spectroscopy. The antimicrobial activity data revealed that the synthesized derivatives possess good antibacterial and antifungal activity which is attributed due to the presence of the heterocyclic ring; further, the activity increased with the introduction of a methoxy group in the structure.

Conclusions: New pyrrole chalcone derivatives act as significant antimicrobial agents, easy work-up procedure and reaction take place with minimum side product. Antimicrobial activity report provides an interesting template for the syntheses of new antimicrobial agents and may be helpful for the design of new therapeutic tools.

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