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DABCO Catalyzed Green and Efficient Synthesis of 2-Amino-4H-Pyrans and Their Biological Evaluation as Antimicrobial and Anticancer Agents

Author(s):

Amit Shivajirao Waghmare, Shivaji Sandu Pandit* and Dayanand M Suryawanshi   Pages 1 - 8 ( 8 )

Abstract:


Aim and Objective: 4H-pyran is one of the most well-known groups of synthetic heterocyclic compounds and it has attracted considerable attention of chemists in recent years because of their extensive range of biological and pharmaceutical activities. These compounds are used as antibacterial, anticancer agents, anti-coagulants, spasmolytics and anti-anaphylactic. 4Hpyran derivatives are utilized in cosmetics, pigments, biodegradable agrochemicals as well as photoactive materials. In addition, 4H-pyrans are also helpful as cognitive enhancers for the treatment of neuro degenerative diseases, including Alzheimer’s disease, as well as for the treatment of schizophrenia and myoclonus. 4H-pyran derivatives are also potential calcium channel antagonists [8] which are structurally similar to biologically active 1,4-dihydropyridines. Therefore, the synthesis of 2-amino-4H-pyrans and their derivatives has attracted much attention in organic synthesis.

Materials and Methods: Some of the synthesized compounds were screened for their antimicrobial activity in vitro by broth dilution method with two gram negative bacteria (Escherichia coli MTCC 442, Pseudomonas aeruginosa MTCC 441), two gram positive bacteria (Staphylococcus aureus MTCC 96, Streptococcus pyogenes MTCC 443) and two fungal strains (Candida albicans MTCC 227, Aspergillus niger MTCC 282) using gentamycin, ampicillin, chloramphenicol, ciprofloxacin, norfloxacin, nystatin and greseofulvin as standard drugs. Eight of the synthesized compounds (4b, 4c, 4k, 4l, 4m, 4n, 4p, and 4u) were selected for screening of their anticancer activity against human astrocytoma-glioblastoma cell line (U373MG).

Results: Antimicrobial study revealed that Compound 4p showed moderate activity against P. aeruginosa. Compounds 4c showed highest activity against S. pyogenes. Also anticancer activity showed that compound 4k is more active against human astrocytoma-glioblastoma cell line (U373MG) as compared to other compounds. Table 4 also shows that, among the tested compounds 4k has good GI50 value than other compounds.

Conclusion: We have developed a simple, rapid, and most efficient green protocol for the synthesis of 2-amino-4H-pyran derivatives using highly inexpensive and easily available DABCO as an efficient catalyst under grinding and solvent free condition at room temperature. Some of the synthesized compounds show good antimicrobial and anticancer activity.

Keywords:

DABCO, 2-amino-4H-pyrans, multi-component reaction, solvent-free, antimicrobial activity, anticancer activity.

Affiliation:

Post Graduate and Research Centre, Department of Chemistry, Padmashri Vikhe Patil College of Arts, Science and Commerce, Pravaranagar, Ahmednagar 413713 (MS), Post Graduate and Research Centre, Department of Chemistry, Padmashri Vikhe Patil College of Arts, Science and Commerce, Pravaranagar, Ahmednagar 413713 (MS), Department of Chemistry, Annasaheb Awate Arts, Commerece and Science College, Manchar, Ambegaon, Pune 410503(MS)



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