Synthesis and Characterization of New Functionalized 1,2,3-Triazole-Based Acetaminophen Derivatives via Click Chemistry from Expired Commercial Acetaminophen Tablets
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials and Instruments
2.2. General Procedure for the Synthesis of 1,2,3-Triazole-Based APAP Derivatives 5a–f
2.3. Spectroscopic Characterization
3. Results and Discussion
3.1. Chemistry
3.2. In Silico ADMET Prediction of Physicochemical Properties (Lipinski descriptors) of Prepared Triazole-APAP Hybrids
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Entry | Solvent | Catalyst | Additive: mol% NaAsC b | Load Catalyst (mol%) | Time (h) | Yield (%) c |
---|---|---|---|---|---|---|
1 | tert-BuOH:H2O 1:1 | CuSO4.5H2O | 15 | 10 | 18 | 83 |
2 | tert-BuOH:H2O 1:1 | CuSO4.5H2O | 10 | 5 | 18 | 86 |
3 | tert-BuOH:H2O 1:1 | CuSO4.5H2O | 1 | 0.5 | 13 | 85 |
4 | tert-BuOH:H2O 1:1 | [CuBr(PPh3)3] | - | 5 | 18 | 90 |
5 | tert-BuOH:H2O 1:1 | [CuBr(PPh3)3] | - | 1 | 18 | 92 |
6 | tert-BuOH:H2O 1:1 | [CuBr(PPh3)3] | - | 1 | 12 | 90 |
7 | tert-BuOH:H2O 1:1 | [CuBr(PPh3)3] | - | 1 | 9 | 93 |
8 | tert-BuOH:H2O 1:1 | [CuBr(PPh3)3] | - | 0.5 | 11 | 87 |
9 | CH3CN | [CuBr(PPh3)3] | - | 1 | 12 | 73 |
10 | CP | [CuBr(PPh3)3] | - | 1 | 18 | NR d |
Comp. | MW b | cLogP c | HBA d | HBD e | ROTB f | TPSA g | n Violations |
---|---|---|---|---|---|---|---|
5a | 290.32 | 0.60 | 7 | 2 | 7 | 89.28 | 0 |
5b | 322.37 | 2.56 | 6 | 1 | 6 | 69.05 | 0 |
5c | 342.79 | 2.92 | 6 | 1 | 5 | 69.05 | 0 |
5d | 434.24 | 3.32 | 6 | 1 | 5 | 69.05 | 0 |
5e | 324.34 | 1.76 | 7 | 2 | 5 | 89.28 | 0 |
5f | 352.35 | 2.15 | 8 | 2 | 6 | 106.35 | 0 |
6a | 353.22 | 1.97 | 6 | 1 | 7 | 69.05 | 0 |
7a | 335.32 | 1.86 | 10 | 1 | 9 | 124.11 | 0 |
APAP | 151.16 | 0.68 | 3 | 2 | 1 | 49.33 | 0 |
APAP-ONO2 | 296.28 | 2.17 | 8 | 1 | 9 | 110.46 | 0 |
Comp. | Mut b | Tum c | Irr d | Rep e | Drug-Likeness | Drug-Score |
---|---|---|---|---|---|---|
5a | −0.75 | 0.62 | ||||
5b | 1.72 | 0.78 | ||||
5c | 1.06 | 0.70 | ||||
5d | 0.65 | 0.59 | ||||
5e | 0.46 | 0.72 | ||||
5f | −0.52 | 0.59 | ||||
6a | −8.16 | 0.12 | ||||
7a | −0.71 | 0.59 | ||||
APAP | 1.93 | 0.20 | ||||
APAP-ONO2 | −8.25 | 0.45 |
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Kouznetsov, V.V.; Calderón Lamus, D.; Puerto Galvis, C.E. Synthesis and Characterization of New Functionalized 1,2,3-Triazole-Based Acetaminophen Derivatives via Click Chemistry from Expired Commercial Acetaminophen Tablets. Reactions 2023, 4, 329-341. https://doi.org/10.3390/reactions4030020
Kouznetsov VV, Calderón Lamus D, Puerto Galvis CE. Synthesis and Characterization of New Functionalized 1,2,3-Triazole-Based Acetaminophen Derivatives via Click Chemistry from Expired Commercial Acetaminophen Tablets. Reactions. 2023; 4(3):329-341. https://doi.org/10.3390/reactions4030020
Chicago/Turabian StyleKouznetsov, Vladimir V., Daniela Calderón Lamus, and Carlos E. Puerto Galvis. 2023. "Synthesis and Characterization of New Functionalized 1,2,3-Triazole-Based Acetaminophen Derivatives via Click Chemistry from Expired Commercial Acetaminophen Tablets" Reactions 4, no. 3: 329-341. https://doi.org/10.3390/reactions4030020