Home | Articles
Published on:February 2019
Indian Journal of Pharmaceutical Education and Research, 2019; 53(2):286-300
Original Article | doi:10.5530/ijper.53.2.37

Ultrasound Assisted Synthesis, Characterization and Antimicrobial Evaluation of Novel Oxazolidinone- Biphenyl Chalcone Hybrid Derivatives


Authors and affiliation (s):

Naresh Panigrahi1,2*, Swastika Ganguly2, Jagadeesh Panda3

1Department of Pharmaceutical Chemistry, GITAM Institute of Pharmacy, GITAM Deemed to be University, Rushikonda, Visakhapatnam, 530045, Andhra Pradesh, INDIA.

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, Andhra Pradesh, INDIA.

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.

Key words: Buchwald’s Protocol, Ultrasound (US) irradiation, Lithium hydroxide monohydrate (LiOH.H2O), Aryl aldehydes, Biphenyl chalcones, 5-chloromethyloxazolidinone.

 

Articles in PDF, ePUB and Full text are attached to this page. In order to download, print or access these formats you must be logged in.
CAPTCHA
This question is for testing whether you are a human visitor and to prevent automated spam submissions.
12 + 1 =
Solve this simple math problem and enter the result. E.g. for 1+3, enter 4.




 

User login

CAPTCHA
This question is for testing whether you are a human visitor and to prevent automated spam submissions.
4 + 2 =
Solve this simple math problem and enter the result. E.g. for 1+3, enter 4.

The Official Journal of Association of Pharmaceutical Teachers of India (APTI)
(Registered under Registration of Societies Act XXI of 1860 No. 122 of 1966-1967, Lucknow)

Indian Journal of Pharmaceutical Education and Research (IJPER) [ISSN-0019-5464] is the official journal of Association of Pharmaceutical Teachers of India (APTI) and is being published since 1967.

DOI HISTORY

IJPER uses reference linking service using Digital Object Identifiers (DOI) by Crossref. Articles from the year 2013 are being assigned DOIs for its permanent URLs