Ultrasound Assisted Synthesis, Characterization and Antimicrobial Evaluation of Novel OxazolidinoneBiphenyl Chalcone Hybrid Derivatives
Naresh Panigrahi2★, Swastika Ganguly2, Jagadeesh Panda3★ Corresponding author
- 1Department of Pharmaceutical Chemistry, GITAM Institute of Pharmacy, GITAM Deemed to be University, Rushikonda.
- 2Department of Pharmaceutical Sciences and Technology, Birla Institute of Technology, Mesra, Ranchi, 835 215, Jharkhand, INDIA.
- 3Department of Pharmaceutical Chemistry, Raghu College of Pharmacy, Dakamarri, Bheemunipatnam, Visakhapatnam, 531162.
CORRESPONDENCE
Naresh Panigrahi
Department of Pharmaceutical Sciences and Technology, Birla Institute of Technology, Mesra, Ranchi, 835 215, Jharkhand, INDIA.
Received: 30-10-2018; Revised: 28-12-2018; Accepted: 18-01-2019.
Volume 53, Issue 2 · pp. 286–300 · PUBLISHED 2019 · DOI: 10.5530/ijper.53.2.37
ABSTRACT
Objective: The main objective of our present study, is to potentiate the antibacterial activity of biphenyl chalcones and oxazolidinones, thus in order to achieve the potent antibacterial agents, we coupled both derivatives by using green chemistry approach for Buchwald’s protocol under ultrasound irradiation. Methodology: Ultrasonication technique was used to couple a series of 24 novel bromo-biphenyl-chalcone derivatives and 5-chloromethyl-oxazolidinone in the presence of copper iodide (CuI) (10 mol %) for the amidation of chalcones and (±)-trans-1,2-diaminocyclohexane was used to solubilize CuI and potassium carbonate (K2CO3) as base, which provided the products in good yields after short reaction times under mild conditions. Results and Discussion: Herewith we report the synthesis of 24 novel oxazolidinone-biphenyl chalcone hybrid derivatives (7a-7x). All the synthesized compounds were characterized by spectral data and evaluated for in vitro antibacterial and antifungal activities. Antibacterial and antifungal activities were tested using the serial dilution method. From the screening studies it was observed that compounds 7c to 7g have shown significant antibacterial activities against the both the strains of gram-positive and gram-negative bacteria at 3.125 µg/ml when compared to the standard drugs ciprofloxacin and linezolid and were as other compounds showed moderate to weak activities. In case of antifungal studies the compounds 7e-7g showed moderate activities at 12.5 µg/ml compared to standard fluconazole and whereas other compounds showed weak activities. Conclusion: We have developed an experimentally simple, efficient, short time and high yielding CuI-mediated N-arylation of oxazolidinones under ultrasound irradiation with a simple set up at room temperature. This approach would be a worthwhile in the development of green chemistry protocols. Compounds 7c to 7g have shown significant antibacterial activities against the both the strains of gram-positive and gram-negative bacteria.
KEYWORDS
REFERENCES
As publishedShowing references and in-text citations exactly as published.
Cite this article
SELECT FORMAT
Panigrahi, N., Ganguly, S., & Panda, J. (2019). Ultrasound Assisted Synthesis, Characterization and Antimicrobial Evaluation of Novel OxazolidinoneBiphenyl Chalcone Hybrid Derivatives. Indian Journal of Pharmaceutical Education and Research, 53(2), 286–300. https://doi.org/10.5530/ijper.53.2.37