Curcumin Analogues with Aldose Reductase Inhibitory Activity: Synthesis, Biological Evaluation, and Molecular Docking
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemistry
2.2. Synthesis of Curcumin Analogues
2.3. Characterization of the Compounds Was Carried out Using Their Melting Point (mp), IR, 1H NMR, and Mass Spectral Data as Follows
2.4. Determination of Bovine Lens ARI Activity of Curcuminoids
2.5. Molecular Docking Study
3. Results and Discussion
3.1. Chemistry
3.2. AR Inhibition Study
3.3. Molecular Docking
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Entry | Product | Time (hr.) | Yield (%) | Entry | Product | Time (hr.) | Yield (%) |
---|---|---|---|---|---|---|---|
8a | 2 | 85 | 9e | 2 | 84 | ||
8b | 2 | 84 | 9f | 4 | 70 | ||
8c | 2.5 | 85 | 9g | 2 | 82 | ||
8d | 2 | 85 | 9h | 3.5 | 75 | ||
8e | 2 | 82 | 9i | 3 | 74 | ||
8f | 2.5 | 80 | 10a | 2 | 85 | ||
8g | 2 | 84 | 10b | 2 | 84 | ||
8h | 2.5 | 85 | 10c | 3 | 82 | ||
8i | 2 | 84 | 10d | 2 | 84 | ||
8j | 2.5 | 82 | 10e | 2 | 85 | ||
8k | 3 | 80 | 10f | 3.5 | 80 | ||
9a | 2 | 80 | 10g | 2 | 84 | ||
9b | 2 | 78 | 10h | 3 | 81 | ||
9c | 2.5 | 78 | 10i | 3 | 80 | ||
9d | 3.5 | 80 |
Entry | Inhibition (%) a | IC50 (µM) b | Entry | Inhibition (%) a | IC50 (µM) b |
---|---|---|---|---|---|
8a | 66.3 ± 1.3 | 6.04 ± 0.32 | 9e | 75.4 ± 1.9 | 5.78 ± 0.13 |
8b | 64.4 ± 1.2 | 6.83 ± 0.27 | 9f | 66.7 ± 1.6 | 6.65 ± 0.31 |
8c | 61.7 ± 1.1 | 6.23 ± 0.21 | 9g | 68.7 ± 1.8 | 6.18 ± 0.29 |
8d | 74.4 ± 1.6 | 5.73 ± 0.28 | 9h | 65.4 ± 1.5 | 6.72 ± 0.26 |
8e | 64.2 ± 1.2 | 6.80 ± 0.24 | 9i | 63.6 ± 1.3 | 7.00 ± 0.30 |
8f | 68.4 ± 1.4 | 6.23 ± 0.18 | 10a | 67.5 ± 1.7 | 6.45 ± 0.21 |
8g | 67.5 ± 1.5 | 6.62 ± 0.33 | 10b | 58.7 ± 1.0 | 6.54 ± 0.19 |
8h | 63.5 ± 1.3 | 5.95 ± 0.27 | 10c | 62.4 ± 1.1 | 6.80 ± 0.16 |
8i | 66.5 ± 1.8 | 6.12 ± 0.16 | 10d | 54.1 ± 0.9 | 8.01 ± 0.32 |
8j | 56.8 ± 1.2 | 6.08 ± 0.14 | 10e | 65.7 ± 1.5 | 6.57 ± 0.21 |
8k | 64.4 ± 1.4 | 6.78 ± 0.23 | 10f | 71.4 ± 1.7 | 5.85 ± 0.16 |
9a | 53.1 ± 0.9 | 9.02 ± 0.28 | 10g | 68.6 ± 1.6 | 5.10 ± 0.14 |
9b | 58.8 ± 1.0 | 10.65 ± 0.34 | 10h | 67.3 ± 1.6 | 6.62 ± 0.29 |
9c | 67.8 ± 1.7 | 5.11 ± 0.11 | 10i | 64.6 ± 1.4 | 6.70 ± 0.15 |
9d | 66.7 ± 1.6 | 6.64 ± 0.15 | Quercetin | 81.5 ± 2.2 | 5.01 ± 0.09 |
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Kondhare, D.; Deshmukh, S.; Lade, H. Curcumin Analogues with Aldose Reductase Inhibitory Activity: Synthesis, Biological Evaluation, and Molecular Docking. Processes 2019, 7, 417. https://doi.org/10.3390/pr7070417
Kondhare D, Deshmukh S, Lade H. Curcumin Analogues with Aldose Reductase Inhibitory Activity: Synthesis, Biological Evaluation, and Molecular Docking. Processes. 2019; 7(7):417. https://doi.org/10.3390/pr7070417
Chicago/Turabian StyleKondhare, Dasharath, Sushma Deshmukh, and Harshad Lade. 2019. "Curcumin Analogues with Aldose Reductase Inhibitory Activity: Synthesis, Biological Evaluation, and Molecular Docking" Processes 7, no. 7: 417. https://doi.org/10.3390/pr7070417