Microwave assisted one-pot catalyst free green synthesis of new methyl-7-amino-4-oxo-5-phenyl-2-thioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carboxylates as potent in vitro antibacterial and antifungal activity
An efficiently simple protocol for the synthesis of methyl 7 amino-4-oxo-5-phenyl-2-thioxo-2, 3, 4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carboxylates via one-pot three component condensation pathway is established via microwave irradiation using varied benzaldehyde derivatives, methylcyanoacetat...
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| Format: | Article |
| Language: | English |
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Elsevier
2015-11-01
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| Series: | Journal of Advanced Research |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2090123214001301 |
| _version_ | 1818970033924079616 |
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| author | Ajmal R. Bhat Aabid H. Shalla Rajendra S. Dongre |
| author_facet | Ajmal R. Bhat Aabid H. Shalla Rajendra S. Dongre |
| author_sort | Ajmal R. Bhat |
| collection | DOAJ |
| description | An efficiently simple protocol for the synthesis of methyl 7 amino-4-oxo-5-phenyl-2-thioxo-2, 3, 4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carboxylates via one-pot three component condensation pathway is established via microwave irradiation using varied benzaldehyde derivatives, methylcyanoacetate and thio-barbituric acid in water as a green solvent. A variety of functionalized substrates were found to react under this methodology due to its easy operability and offers several advantages like, high yields (78–94%), short reaction time (3–6 min), safety and environment friendly without used any catalyst. The synthesized compounds (4a–4k) showed comparatively good in vitro antimicrobial and antifungal activities against different strains. The Compounds 4a, 4b, 4c, 4d 4e and 4f showed maximum antimicrobial activity against Staphylococcus aureus, Bacillus cereus (gram-positive bacteria), Escherichia coli, Klebshiella pneumonia, Pseudomonas aeruginosa (gram-negative bacteria). The synthesized compound 4f showed maximum antifungal activity against Aspergillus Niger and Penicillium chrysogenum strains. Streptomycin is used as standard for bacterial studies and Mycostatin as standards for fungal studies. Structure of all newly synthesized products was characterized on the basis of IR, 1H NMR, 13C NMR and mass spectral analysis. |
| first_indexed | 2024-12-20T14:30:03Z |
| format | Article |
| id | doaj.art-b8a138cb72544fa0aa0d7fb7b80ab308 |
| institution | Directory Open Access Journal |
| issn | 2090-1232 2090-1224 |
| language | English |
| last_indexed | 2024-12-20T14:30:03Z |
| publishDate | 2015-11-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Advanced Research |
| spelling | doaj.art-b8a138cb72544fa0aa0d7fb7b80ab3082022-12-21T19:37:40ZengElsevierJournal of Advanced Research2090-12322090-12242015-11-016694194810.1016/j.jare.2014.10.007Microwave assisted one-pot catalyst free green synthesis of new methyl-7-amino-4-oxo-5-phenyl-2-thioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carboxylates as potent in vitro antibacterial and antifungal activityAjmal R. Bhat0Aabid H. Shalla1Rajendra S. Dongre2Department of Chemistry, R.T.M. Nagpur University, Nagpur 440033, IndiaIslamic University of Science and Technology, Kashmir 192122, IndiaDepartment of Chemistry, R.T.M. Nagpur University, Nagpur 440033, IndiaAn efficiently simple protocol for the synthesis of methyl 7 amino-4-oxo-5-phenyl-2-thioxo-2, 3, 4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carboxylates via one-pot three component condensation pathway is established via microwave irradiation using varied benzaldehyde derivatives, methylcyanoacetate and thio-barbituric acid in water as a green solvent. A variety of functionalized substrates were found to react under this methodology due to its easy operability and offers several advantages like, high yields (78–94%), short reaction time (3–6 min), safety and environment friendly without used any catalyst. The synthesized compounds (4a–4k) showed comparatively good in vitro antimicrobial and antifungal activities against different strains. The Compounds 4a, 4b, 4c, 4d 4e and 4f showed maximum antimicrobial activity against Staphylococcus aureus, Bacillus cereus (gram-positive bacteria), Escherichia coli, Klebshiella pneumonia, Pseudomonas aeruginosa (gram-negative bacteria). The synthesized compound 4f showed maximum antifungal activity against Aspergillus Niger and Penicillium chrysogenum strains. Streptomycin is used as standard for bacterial studies and Mycostatin as standards for fungal studies. Structure of all newly synthesized products was characterized on the basis of IR, 1H NMR, 13C NMR and mass spectral analysis.http://www.sciencedirect.com/science/article/pii/S2090123214001301Microwave irradiationAntibacterial activityThio-barbituric acidMethylcyanoacetateUracilsWater-solvent |
| spellingShingle | Ajmal R. Bhat Aabid H. Shalla Rajendra S. Dongre Microwave assisted one-pot catalyst free green synthesis of new methyl-7-amino-4-oxo-5-phenyl-2-thioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carboxylates as potent in vitro antibacterial and antifungal activity Journal of Advanced Research Microwave irradiation Antibacterial activity Thio-barbituric acid Methylcyanoacetate Uracils Water-solvent |
| title | Microwave assisted one-pot catalyst free green synthesis of new methyl-7-amino-4-oxo-5-phenyl-2-thioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carboxylates as potent in vitro antibacterial and antifungal activity |
| title_full | Microwave assisted one-pot catalyst free green synthesis of new methyl-7-amino-4-oxo-5-phenyl-2-thioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carboxylates as potent in vitro antibacterial and antifungal activity |
| title_fullStr | Microwave assisted one-pot catalyst free green synthesis of new methyl-7-amino-4-oxo-5-phenyl-2-thioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carboxylates as potent in vitro antibacterial and antifungal activity |
| title_full_unstemmed | Microwave assisted one-pot catalyst free green synthesis of new methyl-7-amino-4-oxo-5-phenyl-2-thioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carboxylates as potent in vitro antibacterial and antifungal activity |
| title_short | Microwave assisted one-pot catalyst free green synthesis of new methyl-7-amino-4-oxo-5-phenyl-2-thioxo-2,3,4,5-tetrahydro-1H-pyrano[2,3-d]pyrimidine-6-carboxylates as potent in vitro antibacterial and antifungal activity |
| title_sort | microwave assisted one pot catalyst free green synthesis of new methyl 7 amino 4 oxo 5 phenyl 2 thioxo 2 3 4 5 tetrahydro 1h pyrano 2 3 d pyrimidine 6 carboxylates as potent in vitro antibacterial and antifungal activity |
| topic | Microwave irradiation Antibacterial activity Thio-barbituric acid Methylcyanoacetate Uracils Water-solvent |
| url | http://www.sciencedirect.com/science/article/pii/S2090123214001301 |
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