Inhibitory Potential of New Phenolic Hydrazide-Hydrazones with a Decoy Substrate Fragment towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies
Abstract
:1. Introduction
2. Results and Discussion
2.1. Syntheses and Characterizations
2.2. Kinetic Studies
2.3. Docking Studies
3. Materials and Methods
3.1. Synthesis of Aroylhydrazones 3–5
3.2. Reaction Condition and Kinetic Calculations
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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No. | Ar | R | Yield, (%) | Mp, (°C) | C=O a,b | N–H b,c | C=N b | CAr-O b |
---|---|---|---|---|---|---|---|---|
3a | 3-tBu-2-HO-5-MeC6H2 | Me | 84 | 231–233 | 1654 | 1614 | 1565 | 1239 |
3b | 3-tBu-2-HO-5-MeC6H2 | 4-HOC6H4CH2 | 85 | 242–244 | 1654 | 1612 | 1552 | 1261 |
4a | 3-tBu-2-HO-5-MeC6H2 | 3-pyridyl | 93 | 230–232 | 1638 | 1590 | 1552 | 1261 |
4b | 3-tBu-2-HO-5-MeC6H2 | C6H5 | 96 | 246–248 | 1635 | 1612 | 1561 | 1264 |
4c | 3-tBu-2-HO-5-MeC6H2 | 3-MeOC6H4 | 93 | 238–240 | 1633 | 1584 | 1560 | 1241 |
4d | 3-tBu-2-HO-5-MeC6H2 | 4-MeOC6H4 | 81 | 243–244 | 1636 | 1605 | 1537 | 1235 |
4e | 3-tBu-2-HO-5-MeC6H2 | 2-HOC6H4 | 95 | 252–254 | 1637 | 1615 | 1560 | 1235 |
4f | 3-tBu-2-HO-5-MeC6H2 | 3,5-(HO)2C6H3 | 83 | 246 d | 1643 | 1583 | 1556 | 1265 |
4g | 3,5-(tBu)2-2-HOC6H2 | 2-HOC6H4 | 97 | 233–235 e | 1636 | 1584 | 1554 | 1247 |
4h | 3,5-(tBu)2-2-HOC6H2 | 3-HOC6H4 | 98 | 273–274 | 1638 | 1611 | 1567 | 1251 |
4i | 3,5-(tBu)2-2-HOC6H2 | 3,5-(HO)2C6H3 | 99 | 266 d | 1599 | 1583 | 1549 | 1234 |
4j | 3-tBu-2-HOC6H3 | 2-HOC6H4 | 98 | 218–220 | 1630 | 1610 | 1552 | 1231 |
4k | 3-tBu-2-HOC6H3 | 3-HOC6H4 | 90 | 225–228 | 1648 | 1590 | 1567 | 1240 |
4l | 3-tBu-2-HOC6H3 | 3,5-(HO)2C6H3 | 84 | 217–220 | 1591 | 1591 | 1557 | 1262 |
4m | 2-HO-3-PhC6H3 | 2-HOC6H4 | 83 | 224–227 | 1601 | 1580 | 1559 | 1231 |
4n | 2-HO-3-PhC6H3 | 3-HOC6H4 | 94 | 207–209 | 1651 | 1592 | 1527 | 1227 |
4o | 2-HO-3-PhC6H3 | 3,5-(HO)2C6H3 | 91 | 241–243 | 1655 | 1592 | 1544 | 1254 |
5a | 3-tBu-2-HO-5-MeC6H2 | 2-(1-hydroxynaphthyl) | 92 | 215–217 | 1616 | 1581 | 1532 | 1250 |
5b | 2-HO-3-PhC6H3 | 2-(1-hydroxynaphthyl) | 82 | 226–228 | 1628 | 1600 | 1532 | 1249 |
5c | 3,5-(tBu)2-2-HOC6H2 | 2-(1-hydroxynaphthyl) | 95 f | 121–123 | 1611 | 1584 | 1563 | 1250 |
5d | 3-tBu-2-HOC6H3 | 2-(1-hydroxynaphthyl) | 99 | 220–222 | 1623 | 1602 | 1565 | 1252 |
No. | Ar | R | KI, µM | R2 | Inhibition Type |
---|---|---|---|---|---|
3a | 3-tBu-2-HO-5-MeC6H2 | Me | – a | – | – b |
3b | 3-tBu-2-HO-5-MeC6H2 | 4-HOC6H4CH2 | 49.2 | 0.960 | uncompetitive |
4a | 3-tBu-2-HO-5-MeC6H2 | 3-pyridyl | – c | – | – b |
4b | 3-tBu-2-HO-5-MeC6H2 | C6H5 | 82.0 | 0.996 | competitive |
4c | 3-tBu-2-HO-5-MeC6H2 | 3-MeOC6H4 | 17.4 | 0.974 | non-competitive |
4d | 3-tBu-2-HO-5-MeC6H2 | 4-MeOC6H4 | 25.8 | 0.984 | competitive |
4e | 3-tBu-2-HO-5-MeC6H2 | 2-HOC6H4 | 150.0 | 0.958 | uncompetitive |
4f | 3-tBu-2-HO-5-MeC6H2 | 3,5-(HO)2C6H3 | 32.3 | 0.982 | competitive |
4g | 3,5-(tBu)2-2-HOC6H2 | 2-HOC6H4 | 52.6 | 0.998 | non-competitive |
4h | 3,5-(tBu)2-2-HOC6H2 | 3-HOC6H4 | 18.9 | 0.996 | competitive |
4i | 3,5-(tBu)2-2-HOC6H2 | 3,5-(HO)2C6H3 | 55.6 | 0.961 | competitive |
4j | 3-tBu-2-HOC6H3 | 2-HOC6H4 | 65.6 | 0.965 | uncompetitive |
4k | 3-tBu-2-HOC6H3 | 3-HOC6H4 | 35.8 | 0.994 | competitive |
4l | 3-tBu-2-HOC6H3 | 3,5-(HO)2C6H3 | 38.0 | 0.923 | competitive |
4m | 2-HO-3-PhC6H3 | 2-HOC6H4 | 26.4 | 0.982 | competitive |
57.1 | 0.959 | uncompetitive | |||
4n | 2-HO-3-PhC6H3 | 3-HOC6H4 | 233 | 0.976 | competitive |
139 | 0.964 | non-competitive | |||
4o | 2-HO-3-PhC6H3 | 3,5-(HO)2C6H3 | 69.9 | 0.977 | non-competitive |
5a | 3-tBu-2-HO-5-MeC6H2 | 2-(1-hydroxynaphthyl) | 19.0 | 0.993 | competitive |
8.0 | 0.982 | non-competitive | |||
5b | 2-HO-3-PhC6H3 | 2-(1-hydroxynaphthyl) | 25.8 | 0.950 | competitive |
24.3 | 0.999 | non-competitive | |||
5c | 3,5-(tBu)2-2-HOC6H2 | 2-(1-hydroxynaphthyl) | 16.2 | 0.998 | non-competitive |
5d | 3-tBu-2-HOC6H3 | 2-(1-hydroxynaphthyl) | 75.2 | 0.971 | competitive |
55.6 | 0.999 | non-competitive | |||
20 d | 3-tBu-2-HO-5-MeC6H2 | 4-HOC6H4 | 26.4 [31] | – | competitive |
21 d | 3,5-(tBu)2-2-HOC6H2 | 4-HOC6H4 | 17.9 [31] | – | uncompetitive |
22 d | 3-tBu-2-HO-5-MeC6H2 | 3-HOC6H4 | 32.0 [31] | – | non-competitive |
23 d | 2-HO-3-PhC6H3 | 4-MeOC6H4 | ≥1000 [31] | – | – b |
– | NaN3 d | 2.7 [31] | non-competitive |
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Maniak, H.; Talma, M.; Giurg, M. Inhibitory Potential of New Phenolic Hydrazide-Hydrazones with a Decoy Substrate Fragment towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies. Int. J. Mol. Sci. 2021, 22, 12307. https://doi.org/10.3390/ijms222212307
Maniak H, Talma M, Giurg M. Inhibitory Potential of New Phenolic Hydrazide-Hydrazones with a Decoy Substrate Fragment towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies. International Journal of Molecular Sciences. 2021; 22(22):12307. https://doi.org/10.3390/ijms222212307
Chicago/Turabian StyleManiak, Halina, Michał Talma, and Mirosław Giurg. 2021. "Inhibitory Potential of New Phenolic Hydrazide-Hydrazones with a Decoy Substrate Fragment towards Laccase from a Phytopathogenic Fungus: SAR and Molecular Docking Studies" International Journal of Molecular Sciences 22, no. 22: 12307. https://doi.org/10.3390/ijms222212307