Synthesis and Antimicrobial Evaluation of 4H-Pyrans and Schiff Bases Fused 4H-Pyran Derivatives as Inhibitors of Mycobacterium Bovis (BCG)

Document Type : Research article


1 Department of Organic Chemistry, Faculty of Chemistry, Kharazmi University, Tehran, Iran.

2 Phytochemistry Research Center, Department of Pharmacognosy, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran.

3 Drug Design and Bioinformatics Unit, Department of Medical Biotechnology, Biotechnology Research Center, Pasteur Institute of Iran, Tehran, Iran.


The focus of our study is the synthesis and biological activity evaluation of a series of 4H-Pyran compounds and schiff bases fused 4H-Pyran derivatives which are known to possess a wide variety of biological activities. In this paper at first a simple and efficient one-pot synthesis of 4H-Pyran s from the three-component reaction between malononitrile, aldehydes, and active methylene compounds in the presence of N-methylmorpholine (NMM) as catalyst at room temperature is reported, the reaction between these synthesized products and trimethylorthoformateor triethylorthoformateto produce schiff base compounds were also considered. The key advantages of synthesis of 4H-Pyran derivatives are short reaction time, high yield, and simple work-up. Then, these compounds were evaluated for anti-Mycobacterium activity against Mycobacterium bovis (Bacillus Calmette–Guerin). The preliminary results indicated that most of the tested compounds showed relatively good activity against the test organism. Moreover, antifungal activities of these compounds were evaluated. Finally, their effect was more noticeable on Mycobacterium bovis (BCG).


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