Microwave Assisted Synthesis of Some New Thiazolopyrimidine, Thiazolodipyrimidine and Thiazolopyrimidothiazolopyrimidine Derivatives with Potential Antioxidant and Antimicrobial Activity
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
Compound no. | Reaction Yield % | Reaction Time | ||
---|---|---|---|---|
Microwave | Conventional Method | Microwave | Conventional Method | |
1a | 82 | 55 | 5 min | 3 h |
1b | 87 | 58 | 5 min | 3 h |
1c | 70 | 42 | 5 min | 3 h |
1d | 62 | 35 | 5 min | 3 h |
3a | 81 | 56 | 10 min | Overnight |
3b | 85 | 48 | 10 min | Overnight |
3c | 85 | 53 | 10 min | Overnight |
3d | 68 | 40 | 10 min | Overnight |
5a | 82 | 50 | 15 min | 8 h |
5b | 80 | 53 | 15 min | 8 h |
5c | 79 | 44 | 15 min | 8 h |
5d | 69 | 37 | 15 min | 8 h |
7a | 74 | 43 | 5 min | 3 h |
7b | 88 | 52 | 5 min | 3 h |
7c | 83 | 58 | 5 min | 3 h |
2.2. Biological Evaluation
2.2.1. Antioxidant Screening
Compounds | Absorbance of samples (A) | Hemolysis (%) |
---|---|---|
Complete hemolysis with distilled water (B) | 0.660 | - |
Ascorbic acid | 0.026 | 3.93 |
1a | 0.082 | 10.33 |
1b | 0.075 | 9.12 |
1c | 0.090 | 13.01 |
1d | 0.092 | 14.12 |
3a | 0.035 | 5.22 |
3b | 0.031 | 4.68 |
3c | 0.045 | 6.92 |
3d | 0.051 | 8.02 |
5a | 0.115 | 21.60 |
5b | 0.112 | 19.25 |
5c | 0.132 | 24.07 |
5d | 0.130 | 23.12 |
7a | 0.042 | 6.36 |
7b | 0.045 | 6.81 |
7c | 0.043 | 6.51 |
Compounds | Absorbance of sample | Inhibition (%) |
---|---|---|
ABTS control | 0.54 | 0 |
Ascorbic acid | 0.06 | 88.8 |
1a | 0.20 | 63.0 |
1b | 0.23 | 57.4 |
1c | 0.29 | 46.3 |
1d | 0.28 | 48.1 |
3a | 0.10 | 81.5 |
3b | 0.12 | 77.7 |
3c | 0.15 | 72.2 |
3d | 0.13 | 75.9 |
5a | 0.45 | 16.6 |
5b | 0.42 | 22.2 |
5c | 0.48 | 11.1 |
5d | 0.43 | 20.3 |
7a | 0.17 | 68.5 |
7b | 0.19 | 64.8 |
7c | 0.16 | 70.3 |
Compound | Absorbance of Samples |
---|---|
Ascorbic acid | 0.020 |
3a | 0.026 |
3b | 0.029 |
3c | 0.037 |
3d | 0.033 |
2.2.2. Antimicrobial Evaluation
Compd. No. | Inhibition zone (mm) | ||||||
---|---|---|---|---|---|---|---|
Gram-negative | Gram-positive | Fungi Yeast | |||||
E. coli | P. putida | B. subtilis | S. lactis | A. niger | P. sp. | C. albicans | |
1a | 12 | 8 | 6 | 8 | 5 | 5 | 0 |
1b | 14 | 9 | 6 | 7 | 4 | 2 | 0 |
1c | 6 | 3 | 0 | 0 | 2 | 2 | 0 |
1d | 3 | 2 | 0 | 0 | 0 | 0 | 0 |
3a | 15 | 11 | 9 | 6 | 7 | 5 | 0 |
3b | 12 | 7 | 7 | 5 | 7 | 5 | 0 |
3c | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
3d | 2 | 2 | 0 | 0 | 0 | 0 | 0 |
5a | 10 | 7 | 8 | 6 | 4 | 3 | |
5b | 11 | 8 | 9 | 6 | 5 | 2 | |
5c | 4 | 2 | 0 | 0 | 0 | 0 | 0 |
5d | 3 | 0 | 0 | 0 | 0 | 0 | 0 |
7a | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
7b | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
7c | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
Chloram-phenicol® | 22 | 21 | 18 | 19 | 20 | 12 | 0 |
Ampicillin® | 24 | 20 | 19 | 22 | 24 | 14 | 14 |
3. Experimental
3.1. General
3.1.1. Ethyl 4-aryl-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates 1a–d
3.1.2. Ethyl 3-amino-5-aryl-2-cyano-7-methyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylates (3a–d)
3.1.3. Ethyl 9-aryl-7-methyl-2,4-dithioxo-2,3,4,9-tetrahydro-1H-thiazolo[3,2-a:4,5-d']dipyrimidine-8-carboxylates 5a–d
3.1.4. Ethyl 8-methyl-10-(4-methoxyphenyl)-3-substituted-5-thioxo-2-(un)substituted-10H-thiazolo-[3'',2'':1',2']pyrimido[4',5':4,5]thiazolo[3,2-a]pyrimidine-9-carboxylates 7a–c
3.2. Antioxidant Screening
3.2.1. Assay for Erythrocyte Hemolysis
3.2.2. Antioxidant Activity Screening Assay—ABTS Method
3.2.3. Bleomycin-Dependent DNA Damage
3.3. Antimicrobial Screening
4. Conclusions
Acknowledgements
References
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Youssef, M.M.; Amin, M.A. Microwave Assisted Synthesis of Some New Thiazolopyrimidine, Thiazolodipyrimidine and Thiazolopyrimidothiazolopyrimidine Derivatives with Potential Antioxidant and Antimicrobial Activity. Molecules 2012, 17, 9652-9667. https://doi.org/10.3390/molecules17089652
Youssef MM, Amin MA. Microwave Assisted Synthesis of Some New Thiazolopyrimidine, Thiazolodipyrimidine and Thiazolopyrimidothiazolopyrimidine Derivatives with Potential Antioxidant and Antimicrobial Activity. Molecules. 2012; 17(8):9652-9667. https://doi.org/10.3390/molecules17089652
Chicago/Turabian StyleYoussef, Mohamed M., and Mahmoud A. Amin. 2012. "Microwave Assisted Synthesis of Some New Thiazolopyrimidine, Thiazolodipyrimidine and Thiazolopyrimidothiazolopyrimidine Derivatives with Potential Antioxidant and Antimicrobial Activity" Molecules 17, no. 8: 9652-9667. https://doi.org/10.3390/molecules17089652