Utility of 2-thioxo-pyrido[2,3-d]pyrimidinone in synthesis of pyridopyrimido[2,1-b][1,3,5]-thiadiazinones and pyridopyrimido[2,1-b][1,3]thiazinones as antimicrobial agents
Abstract Background Pyridopyrimidines are of current interest because of their extensive variety of biological and pharmacological activities. Results A series of pyrido[2′,3′:4,5]pyrimido[2,1-b][1,3,5]thiadiazinones was obtained by aminomethylation of pyridopyrimidinethione with formaldehyde soluti...
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| Format: | Article |
| Language: | English |
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BMC
2017-06-01
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| Series: | Chemistry Central Journal |
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| Online Access: | http://link.springer.com/article/10.1186/s13065-017-0286-0 |
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| author | Yasser H. Zaki Sobhi M. Gomha Amany M. G. Mohamed |
| author_facet | Yasser H. Zaki Sobhi M. Gomha Amany M. G. Mohamed |
| author_sort | Yasser H. Zaki |
| collection | DOAJ |
| description | Abstract Background Pyridopyrimidines are of current interest because of their extensive variety of biological and pharmacological activities. Results A series of pyrido[2′,3′:4,5]pyrimido[2,1-b][1,3,5]thiadiazinones was obtained by aminomethylation of pyridopyrimidinethione with formaldehyde solution (37%) and different primary aromatic amines. Another series of pyrido[2′,3:4,5]pyrimido[2,1-b][1,3]thiazinones was prepared by Michael addition reaction of pyridopyrimidinethione to the activated double bond of a number of arylidene malononitrile and 2-(benzo[d][1,3]dioxol-5-ylmethylene)malononitrile. The mechanisms of formation of the synthesized compounds were discussed and the assigned structure was established via microanalysis and spectral data (IR, 1H NMR, and Ms.). A comparative study of the biological activity of the synthesized compounds with chloramphenicol and trimethoprim/sulphamethoxazole is shown in Table 1. Generally, all synthesized compounds showed adequate inhibitory effects on the growth of Gram-positive and Gram-negative bacteria. Conclusions In this study, we use a simple (synthetic) strategy for the synthesis of pyrimidothiadiazines, based on their aminomethylation through the Mannich reaction; they have also been synthesized by the application of the Michael addition to activated nitriles. Mechanisms and structures of the newly synthesized compounds were examined: the antimicrobial activity of some selected compounds was evaluated, which demonstrated adequate inhibitory effects. Graphical abstract The strategic structures of the products (7a–g). |
| first_indexed | 2024-12-18T02:20:52Z |
| format | Article |
| id | doaj.art-f20be518beaa4a7594b39b4ee90db332 |
| institution | Directory Open Access Journal |
| issn | 1752-153X |
| language | English |
| last_indexed | 2024-12-18T02:20:52Z |
| publishDate | 2017-06-01 |
| publisher | BMC |
| record_format | Article |
| series | Chemistry Central Journal |
| spelling | doaj.art-f20be518beaa4a7594b39b4ee90db3322022-12-21T21:24:13ZengBMCChemistry Central Journal1752-153X2017-06-0111111010.1186/s13065-017-0286-0Utility of 2-thioxo-pyrido[2,3-d]pyrimidinone in synthesis of pyridopyrimido[2,1-b][1,3,5]-thiadiazinones and pyridopyrimido[2,1-b][1,3]thiazinones as antimicrobial agentsYasser H. Zaki0Sobhi M. Gomha1Amany M. G. Mohamed2Department of Chemistry, Faculty of Science, Beni-Suef UniversityDepartment of Chemistry, Faculty of Science, Cairo UniversityDepartment of Chemistry, Faculty of Science, Cairo UniversityAbstract Background Pyridopyrimidines are of current interest because of their extensive variety of biological and pharmacological activities. Results A series of pyrido[2′,3′:4,5]pyrimido[2,1-b][1,3,5]thiadiazinones was obtained by aminomethylation of pyridopyrimidinethione with formaldehyde solution (37%) and different primary aromatic amines. Another series of pyrido[2′,3:4,5]pyrimido[2,1-b][1,3]thiazinones was prepared by Michael addition reaction of pyridopyrimidinethione to the activated double bond of a number of arylidene malononitrile and 2-(benzo[d][1,3]dioxol-5-ylmethylene)malononitrile. The mechanisms of formation of the synthesized compounds were discussed and the assigned structure was established via microanalysis and spectral data (IR, 1H NMR, and Ms.). A comparative study of the biological activity of the synthesized compounds with chloramphenicol and trimethoprim/sulphamethoxazole is shown in Table 1. Generally, all synthesized compounds showed adequate inhibitory effects on the growth of Gram-positive and Gram-negative bacteria. Conclusions In this study, we use a simple (synthetic) strategy for the synthesis of pyrimidothiadiazines, based on their aminomethylation through the Mannich reaction; they have also been synthesized by the application of the Michael addition to activated nitriles. Mechanisms and structures of the newly synthesized compounds were examined: the antimicrobial activity of some selected compounds was evaluated, which demonstrated adequate inhibitory effects. Graphical abstract The strategic structures of the products (7a–g).http://link.springer.com/article/10.1186/s13065-017-0286-0PyridopyrimidinethioneMichaelAdditionHydrazoneBis-hydrazonePyrazolines |
| spellingShingle | Yasser H. Zaki Sobhi M. Gomha Amany M. G. Mohamed Utility of 2-thioxo-pyrido[2,3-d]pyrimidinone in synthesis of pyridopyrimido[2,1-b][1,3,5]-thiadiazinones and pyridopyrimido[2,1-b][1,3]thiazinones as antimicrobial agents Chemistry Central Journal Pyridopyrimidinethione Michael Addition Hydrazone Bis-hydrazone Pyrazolines |
| title | Utility of 2-thioxo-pyrido[2,3-d]pyrimidinone in synthesis of pyridopyrimido[2,1-b][1,3,5]-thiadiazinones and pyridopyrimido[2,1-b][1,3]thiazinones as antimicrobial agents |
| title_full | Utility of 2-thioxo-pyrido[2,3-d]pyrimidinone in synthesis of pyridopyrimido[2,1-b][1,3,5]-thiadiazinones and pyridopyrimido[2,1-b][1,3]thiazinones as antimicrobial agents |
| title_fullStr | Utility of 2-thioxo-pyrido[2,3-d]pyrimidinone in synthesis of pyridopyrimido[2,1-b][1,3,5]-thiadiazinones and pyridopyrimido[2,1-b][1,3]thiazinones as antimicrobial agents |
| title_full_unstemmed | Utility of 2-thioxo-pyrido[2,3-d]pyrimidinone in synthesis of pyridopyrimido[2,1-b][1,3,5]-thiadiazinones and pyridopyrimido[2,1-b][1,3]thiazinones as antimicrobial agents |
| title_short | Utility of 2-thioxo-pyrido[2,3-d]pyrimidinone in synthesis of pyridopyrimido[2,1-b][1,3,5]-thiadiazinones and pyridopyrimido[2,1-b][1,3]thiazinones as antimicrobial agents |
| title_sort | utility of 2 thioxo pyrido 2 3 d pyrimidinone in synthesis of pyridopyrimido 2 1 b 1 3 5 thiadiazinones and pyridopyrimido 2 1 b 1 3 thiazinones as antimicrobial agents |
| topic | Pyridopyrimidinethione Michael Addition Hydrazone Bis-hydrazone Pyrazolines |
| url | http://link.springer.com/article/10.1186/s13065-017-0286-0 |
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