The Synthesis and the Biological Evaluation of New Thiazolidin-4-one Derivatives Containing a Xanthine Moiety
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Biological Evaluation
2.2.1. Ferric Reducing Power
Sample | EC50 mg/mL | Sample | EC50 mg/mL |
---|---|---|---|
6a | 0.137 ± 0.0036 | 6b | 0.155 ± 0.0038 |
7a1 | 0.109 ± 0.0014 | 7b1 | 0.109 ± 0.0045 |
7a2 | 0.097 ± 0.0018 | 7b2 | 0.102 ± 0.0024 |
7a3 | 0.055 ± 0.0036 | 7b3 | 0.046 ± 0.0015 |
7a4 | 0.096 ± 0.0023 | 7b4 | 0.066 ± 0.0017 |
7a5 | 0.033 ± 0.0019 | 7b5 | 0.027 ± 0.0013 |
7a6 | 0.033 ± 0.0012 | 7b6 | 0.023 ± 0.0011 |
7a7 | 0.058 ± 0.0041 | 7b7 | 0.041 ± 0.0010 |
AA | 0.0075 ± 0.0002 |
2.2.2. Total Antioxidant Activity
Sample | EC50 mg/mL | Sample | EC50 mg/mL |
---|---|---|---|
6a | 0.133 ± 0.0045 | 6b | 0.124 ± 0.0009 |
7a1 | 0.105 ± 0.0025 | 7b1 | 0.090 ± 0.0018 |
7a2 | 0.099 ± 0.0038 | 7b2 | 0.092 ± 0.0008 |
7a3 | 0.048 ± 0.0023 | 7b3 | 0.043 ± 0.0026 |
7a4 | 0.076 ± 0.0025 | 7b4 | 0.099 ± 0.0024 |
7a5 | 0.025 ± 0.0012 | 7b5 | 0.022 ± 0.0013 |
7a6 | 0.033 ± 0.0014 | 7b6 | 0.026 ± 0.0018 |
7a7 | 0.037 ± 0.0007 | 7b7 | 0.043 ± 0.0028 |
AA | 0.0067 ± 0.0003 |
2.2.3. DPPH Radical Scavenging Assay
Sample | EC50 mg/mL | Sample | EC50 mg/mL |
---|---|---|---|
6a | 0.136 ± 0.0006 | 6b | 0.127 ± 0.0013 |
7a1 | 0.094 ± 0.0013 | 7b1 | 0.106 ± 0.0011 |
7a2 | 0.107 ± 0.0018 | 7b2 | 0.101 ± 0.0044 |
7a3 | 0.066 ± 0.0011 | 7b3 | 0.049 ± 0.0006 |
7a4 | 0.077 ± 0.0005 | 7b4 | 0.085 ± 0.0017 |
7a5 | 0.038 ± 0.0044 | 7b5 | 0.038 ± 0.0024 |
7a6 | 0.039 ± 0.0008 | 7b6 | 0.037 ± 0.0037 |
7a7 | 0.048 ± 0.0001 | 7b7 | 0.038 ± 0.0014 |
AA | 0.0065 ± 0.0031 |
2.2.4. ABTS Radical Scavenging Assay
Sample | EC50 mg/mL | Sample | EC50 mg/mL |
---|---|---|---|
6a | 0.074 ± 0.0039 | 6b | 0.069 ± 0.0031 |
7a1 | 0.047 ± 0.0032 | 7b1 | 0.048 ± 0.0014 |
7a2 | 0.049 ± 0.0026 | 7b2 | 0.041 ± 0.0041 |
7a3 | 0.037 ± 0.0015 | 7b3 | 0.031 ± 0.0035 |
7a4 | 0.043 ± 0.0028 | 7b4 | 0.040 ± 0.0029 |
7a5 | 0.027 ± 0.0017 | 7b5 | 0.024 ± 0.0047 |
7a6 | 0.025 ± 0.0012 | 7b6 | 0.021 ± 0.0041 |
7a7 | 0.036 ± 0.0098 | 7b7 | 0.030 ± 0.0017 |
AA | 0.0055 ± 0.0024 |
3. Experimental
3.1. General Procedures
3.2. Synthetic Procedures
3.2.1. General Procedure for the Preparation of 1-[2-(1,3-Dimethylxanthin-7-yl)acetyl]-4-(4-R-phenyl)-thiosemicarbazides 5a, 5b
3.2.2. General Procedure for the Preparation of 2-{2-[2-(1,3-Dimethylxanthin-7-yl)acetyl]hydrazono}-3-(4-R-phenyl) Thiazolidin-4-ones (R = H, Cl) 6a, 6b
3.2.3. General Procedure for the Preparation of 2-{2-[2-(1,3-Dimethylxanthin-7-yl)acetyl]hydrazono}-3-(4-R1-phenyl-5-(R2-benzyliden)thiazolidin-4-ones 7a1-7, 7b1-7
3.3. Biological Evaluation
3.3.1. Antioxidant Assays
3.3.2. Ferric Reducing Power
3.3.3. Total Antioxidant Activity
3.3.4. DPPH Radical Scavenging Assay
3.3.5. ABTS Radical Scavenging Assay
3.3.6. Statistical Analysis
4. Conclusions
Acknowledgments
Conflicts of Interest
References
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Lupascu, F.G.; Dragostin, O.M.; Foia, L.; Lupascu, D.; Profire, L. The Synthesis and the Biological Evaluation of New Thiazolidin-4-one Derivatives Containing a Xanthine Moiety. Molecules 2013, 18, 9684-9703. https://doi.org/10.3390/molecules18089684
Lupascu FG, Dragostin OM, Foia L, Lupascu D, Profire L. The Synthesis and the Biological Evaluation of New Thiazolidin-4-one Derivatives Containing a Xanthine Moiety. Molecules. 2013; 18(8):9684-9703. https://doi.org/10.3390/molecules18089684
Chicago/Turabian StyleLupascu, Florentina Geanina, Oana Maria Dragostin, Liliana Foia, Dan Lupascu, and Lenuta Profire. 2013. "The Synthesis and the Biological Evaluation of New Thiazolidin-4-one Derivatives Containing a Xanthine Moiety" Molecules 18, no. 8: 9684-9703. https://doi.org/10.3390/molecules18089684