Multi-Component One-Pot Synthesis and Antimicrobial Activities of 3-Methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydro-pyrazolo[5,4-b]pyrimidino[5,4-e]pyridine-5-one and Related Derivatives
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Biological Results
3. Experimental
3.1. General
3.2. Synthesis of 3-Methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydropyrazolo[5,4-b]pyrimidino[5,4-e]pyridin-5-one (6)
3.3. General Procedure for the Preparation of 7a–f
3.4. 8-Ethyl-7-ethylthio-3-methyl-1,4-diphenyl-4,6,9-trihydropyrazolo[5,4-b]pyrimidino[5,4-e]pyridin-5-one (8) and 6-Ethyl-7-ethylthio-3-methyl-1,4-diphenyl-4,6,9-trihydropyrazolo[5,4-b]pyrimidino[5,4-e]pyridin-5-one (9)
3.5. 7-(2,4-Dinitrophenylthio)-3-methyl-1,4-diphenyl-4,6,9-trihydropyrazolo[5,4-b]pyrimidino[5,4-e] pyridin-5-one (10)
3.6. 3-Methyl-8-nitro-1,4-diphenyl-4,6,13-trihydrobenzothiazolo[3',2'-2,1]pyrimidino[5,4-e] pyrazolo-[5,4-b]pyridin-5-one (11)
3.7. 6-Ethyl-7-hydrazino-3-methyl-1,4-diphenyl-4,6,9-trihydropyrazolo[5,4-b]pyrimidino[5,4-e]-pyridin-5-one (12)
3.8. General Procedure for the Preparation of 13a–c
3.9. 6-Ethyl-3-methyl-7-(3-methyl-5-oxo(2-pyrazolinyl))-1,4-diphenyl-4,6,9-trihydropyrazolo[5,4-b]-pyrimidino[5,4-e]pyridin-5-one (14)
3.10. 7-(3,5-Dimethylpyrazolyl)-6-ethyl-3-methyl-1,4-diphenyl-4,6,9-trihydropyrazolo[5,4-b]-pyrimidine[5,4-e]pyridin-5-one (15)
3.11. 7-(3-Amino-5-oxo(2-pyrazolinyl))-6-ethyl-3-methyl-1,4-diphenyl-4,6,9-tri-hydropyrazolo[5,4-b]-pyrimidino[5,4-e]pyridin-5-one (16)
3.12. 11-Ethyl-8-methyl-6,9-diphenyl-4,5,9,11-tetrahydropyrazolo[5,4-b]1,2,4-triazolo[4',3'-2,1]-pyrimidino[5,6-e]pyridin-10-one (17)
3.13. 11-Ethyl-8-methyl-6,9-diphenyl-10-oxo-4,5,9,11-tetrahydropyrazolo[5,4-b]1,2,4-triazolo[4',3'-2,1]pyrimidino[5,6-e]pyridin-3(2H)-thione (18)
3.14. General Procedure for the Preparation of 19a–c
3.15. 4-Ethyl-7-methyl-6,9-diphenyl-4,6,10,11-tetrahydropyrazolo[5,4-b]1,2,3,4-tetraazolo[1',5'-1,2]-pyrimidino[5,6-e]pyridin-5-one (20)
3.16. 5-Ethyl-8-methyl-1,2,7,10-tetraphenyl-5,7,11,12-tetrahydro-1H-pyrazolo[5,4-b]1,2,4-triazino[4',3'-2,1]-pyrimidino[5,6-e]pyridin-6-one (21)
3.17. General Procedure for the Preparation of 22a,b
3.18. Antimicrobial Activity
4. Conclusions
Supplementary Materials
Acknowledgements
References
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Sample Availability: Samples of the compounds are available from the authors. |
Compound No. | Diameter of the inihibition zone (mm) MIC (mM) | |||||
---|---|---|---|---|---|---|
S. aureus AUMC B.54 | S. cereus AUMC B.52 | M. luteus AUMC B.112 | E. coli AUMC B.53 | p. aeruginosa AUMC B.73 | S. marcescens AUMC B.55 | |
6 | - | - | - | - | - | - |
7a | - | - | - | - | - | - |
9 | - | - | - | - | - | - |
11 | 8 (2.5) | - | - | - | - | - |
12 | - | 10 (1.25) | 18 (20) | - | - | - |
13b | - | - | - | - | - | - |
17 | - | - | - | - | - | - |
19c | 8 (1.25 ) | 10 (0.15) | 10 (5) | - | - | - |
20 | - | - | - | - | - | - |
22a | 8 (5) | - | - | - | 11 (20) | - |
CHL | 10 (0.08) | 12 (1.25) | 12 (2.5) | 10 (0.08) | 12 (0.3) | 13 (1.25) |
Compound No. | Diameter of the inihibition zone (mm) MIC (mM) | |||||
---|---|---|---|---|---|---|
C. albicans AUMC 418 | G.candidum AUMC 226 | T. rubrum AUMC 1804 | A.flavus AUMC 3214 | F. oxysporum AUMC 5119 | S. brevicaylis AUMC 729 | |
6 | - | - | - | - | - | - |
7a | - | - | - | - | - | - |
9 | - | - | - | - | - | - |
11 | - | 11 (20) | 8 (20) | - | - | 10 (20) |
12 | 9 (2.5) | 15 (5) | 10 (10) | 10 (2.5) | 16 (20) | 20 (5) |
13b | - | - | - | - | - | - |
17 | 10 (20) | - | 24p.i (20) | 10 (20) | 8 (20) | 12 (10) |
19c | 9 (2.5) | 16 (2.5) | 12 (5) | 14 (2.5) | 10 (10) | 28 (5) |
20 | - | - | - | - | - | - |
22a | 10 (0.6) | - | - | - | - | - |
CLO | 12 (0.08) | 14 (0.08) | 35 (0.08) | 15 (0.15) | 14 (0.15) | 24 p.i (0.3) |
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El-Emary, T.I.; El-Mohsen, S.A.A. Multi-Component One-Pot Synthesis and Antimicrobial Activities of 3-Methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydro-pyrazolo[5,4-b]pyrimidino[5,4-e]pyridine-5-one and Related Derivatives. Molecules 2012, 17, 14464-14483. https://doi.org/10.3390/molecules171214464
El-Emary TI, El-Mohsen SAA. Multi-Component One-Pot Synthesis and Antimicrobial Activities of 3-Methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydro-pyrazolo[5,4-b]pyrimidino[5,4-e]pyridine-5-one and Related Derivatives. Molecules. 2012; 17(12):14464-14483. https://doi.org/10.3390/molecules171214464
Chicago/Turabian StyleEl-Emary, Talaat I., and Shawkat A. Abd El-Mohsen. 2012. "Multi-Component One-Pot Synthesis and Antimicrobial Activities of 3-Methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydro-pyrazolo[5,4-b]pyrimidino[5,4-e]pyridine-5-one and Related Derivatives" Molecules 17, no. 12: 14464-14483. https://doi.org/10.3390/molecules171214464