Lipophilicity Studies on Thiosemicarbazide Derivatives
Abstract
:1. Introduction
2. Results and Discussion
2.1. The Relationship between the Retention Parameter logk and the Concentration of Organic Modifier φ
2.2. The Calibration Equation logP vs. logkw
n = 7; r = 0.9976; se = 0.08; F = 1047.8
2.3. Theoretical Calculation clogP
2.4. Correlation of Lipophilicity with Inhibitory Potency towards Bacterial Type IIA Topoisomerases
3. Materials and Methods
3.1. Chromatographic Analysis
3.2. Standard Solutes
3.3. Statistical Analysis
3.4. LogP Calculations
3.5. Quantum-Chemical Calculations
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Not Available. |
Compound | logkw | −S | r | n | F | SD of Estimation | |
---|---|---|---|---|---|---|---|
1 | 2.9992 | 4.3720 | 0.9986 | 7 | 1796.1 | 0.027 | |
2 | 2.5105 | 4.1416 | 0.9983 | 7 | 1487.0 | 0.028 | |
3 | 4.2230 | 6.1166 | 0.9983 | 7 | 1440.4 | 0.043 | |
4 | 3.3130 | 4.8205 | 0.9984 | 7 | 1598.1 | 0.032 | |
5 | 3.4487 | 4.8562 | 0.9987 | 7 | 1864.2 | 0.030 | |
6 | 3.7864 | 5.1137 | 0.9976 | 7 | 1049.6 | 0.042 | |
7 | 3.8283 | 5.6579 | 0.9934 | 7 | 372.8 | 0.078 | |
8 | 3.7422 | 5.0742 | 0.9972 | 7 | 901.4 | 0.045 | |
9 | 3.9422 | 5.3417 | 0.9974 | 7 | 975.2 | 0.045 | |
10 | 3.2498 | 5.7291 | 0.9838 | 7 | 150.3 | 0.124 | |
11 | 3.3324 | 4.8778 | 0.9983 | 7 | 2138.6 | 0.028 | |
12 | 2.4813 | 4.1962 | 0.9992 | 7 | 3260.5 | 0.019 | |
13 | 3.2386 | 4.7076 | 0.9987 | 7 | 1871.6 | 0.029 | |
14 | 4.1453 | 5.6538 | 0.9980 | 7 | 1251.7 | 0.042 | |
15 | 3.9451 | 5.5432 | 0.9964 | 7 | 690.2 | 0.056 | |
16 | 2.0687 | 4.1968 | 0.9993 | 7 | 3508.6 | 0.019 | |
17 | 2.7583 | 4.3297 | 0.9993 | 7 | 3507.0 | 0.019 |
Compound | AlogPs | AclogP | milogP | AlogP | MlogP | XlogP2 | XlogP3 | logkw | logPHPLC |
---|---|---|---|---|---|---|---|---|---|
1 | 0.90 | 1.70 | 1.28 | 1.80 | 1.33 | 1.62 | 2.59 | 2.9992 | 3.0469 |
2 | 1.66 | 1.06 | 1.27 | 1.94 | 1.06 | 1.59 | 2.25 | 2.5105 | 2.5254 |
3 | 2.86 | 2.59 | 2.23 | 2.95 | 3.20 | 3.43 | 3.95 | 4.2300 | 4.3606 |
4 | 2.36 | 2.17 | 2.15 | 2.53 | 2.42 | 2.70 | 3.10 | 3.3130 | 3.3819 |
5 | 2.41 | 2.49 | 2.55 | 3.02 | 2.66 | 3.14 | 3.46 | 3.4487 | 3.5267 |
6 | 2.41 | 2.49 | 2.57 | 3.02 | 2.66 | 3.14 | 3.46 | 3.7864 | 3.8871 |
7 | 3.00 | 2.79 | 2.78 | 3.20 | 2.93 | 3.32 | 3.73 | 3.8283 | 3.9318 |
8 | 2.93 | 2.79 | 2.80 | 3.20 | 2.93 | 3.32 | 3.73 | 3.7422 | 3.8399 |
9 | 2.88 | 2.79 | 2.83 | 3.20 | 2.93 | 3.32 | 3.73 | 3.9422 | 4.0534 |
10 | 2.62 | 1.59 | 1.53 | 2.81 | 2.57 | 2.43 | 3.06 | 3.2498 | 3.3144 |
11 | 2.82 | 2.66 | 3.31 | 3.08 | 3.39 | 3.41 | 3.52 | 3.3324 | 3.4026 |
12 | 1.95 | 2.05 | 2.63 | 2.41 | 2.86 | 2.78 | 3.21 | 2.4813 | 2.4942 |
13 | 1.72 | 2.05 | 3.48 | 2.69 | 2.44 | 3.05 | 3.14 | 3.2386 | 3.3025 |
14 | 3.32 | 3.27 | 3.91 | 3.74 | 3.64 | 4.03 | 4.15 | 4.1453 | 4.2702 |
15 | 3.02 | 2.97 | 3.69 | 3.56 | 3.64 | 3.63 | 3.88 | 3.9451 | 4.0565 |
16 | 1.99 | 2.05 | 1.64 | 2.41 | 2.35 | 2.36 | 2.34 | 2.0687 | 2.0538 |
17 | 1.74 | 2.05 | 2.48 | 2.69 | 1.93 | 2.62 | 2.59 | 2.7583 | 2.7898 |
AlogPs | AclogP | milogP | AlogP | MlogP | XlogP2 | XlogP3 | logkw | logPHPLC | |
---|---|---|---|---|---|---|---|---|---|
AlogPs | 1.0000 | 0.7241 | 0.7833 | 0.9335 | 0.9132 | 0.8906 | 0.8518 | 0.7676 | 0.7676 |
AclogP | 1.0000 | 0.9500 | 0.8541 | 0.8641 | 0.9348 | 0.9403 | 0.9052 | 0.9052 | |
milogP | 1.0000 | 0.8993 | 0.8226 | 0.9282 | 0.8755 | 0.8013 | 0.8013 | ||
AlogP | 1.0000 | 0.9425 | 0.9529 | 0.9177 | 0.8361 | 0.8361 | |||
MlogP | 1.0000 | 0.9632 | 0.9667 | 0.9251 | 0.9251 | ||||
XlogP2 | 1.0000 | 0.9776 | 0.9265 | 0.9265 | |||||
XlogP3 | 1.0000 | 0.9716 | 0.9716 | ||||||
logkw | 1.0000 | 1.0000 | |||||||
logPHPLC | 1.0000 | 1.0000 |
AlogPs | AclogP | milogP | AlogP | MlogP | XlogP2 | XlogP3 | logkw | logPHPLC | |
---|---|---|---|---|---|---|---|---|---|
AlogPs | 1.0000 | 0.9809 | 0.6650 | 0.9168 | 0.9309 | 0.8909 | 0.8564 | 0.8014 | 0.8014 |
AclogP | 1.0000 | 0.7475 | 0.9725 | 0.8927 | 0.9373 | 0.8881 | 0.8839 | 0.8839 | |
milogP | 1.0000 | 0.8199 | 0.7237 | 0.9251 | 0.9135 | 0.9520 | 0.9521 | ||
AlogP | 1.0000 | 0.8142 | 0.9450 | 0.8769 | 0.9510 | 0.9510 | |||
MlogP | 1.0000 | 0.8805 | 0.9201 | 0.7670 | 0.7670 | ||||
XlogP2 | 1.0000 | 0.9712 | 0.9650 | 0.9650 | |||||
XlogP3 | 1.0000 | 0.9136 | 0.9136 | ||||||
logkw | 1.0000 | 1.0000 | |||||||
logPHPLC | 1.0000 | 1.0000 |
Compound | XlogP3 | XlogP2 | Inhibitory Potency IC50 [μM] | ||
---|---|---|---|---|---|
DNA Gyrase | Topo IV | ||||
1 [16] | 2.59 | n.d. * | 14.59 | n.a. ** | |
2 [16] | 2.25 | n.d. | 93.30 | 41.04 | |
18 [17] | 3.59 | n.d. | n.d. | 14 | |
19 [16] | 3.14 | n.d. | 83.63 | n.a. | |
20 [17] | 2.00 | n.d. | n.a. | 90.00 | |
21 [18] | n.d. | 2.82 | n.a. | 14.00 | |
22 [16] | n.d. | 3.09 | n.a. | 63.47 | |
23 [16] | n.d. | 3.09 | 127.68 | 267.04 | |
24 [18] | n.d. | 3.25 | n.a. | 295.00 | |
25 [16] | n.d. | 3.73 | n.a. | n.a. | |
26 [18] | n.d. | 2.25 | n.a. | n.a. | |
27 [16] | n.d. | 1.46 | 64.21 | n.a. | |
28 [18] | n.d. | 3.16 | n.a. | 403.00 | |
29 [18] | n.d. | 2.98 | n.a. | n.a. | |
30 [18] | n.d. | 2.52 | n.a. | n.a. | |
31 [18] | n.d. | 2.68 | n.a. | n.a. | |
32 [18] | n.d. | 3.16 | n.a. | n.a. |
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Paneth, A.; Hawrył, A.; Plech, T.; Hawrył, M.; Świeboda, R.; Janowska, D.; Wujec, M.; Paneth, P. Lipophilicity Studies on Thiosemicarbazide Derivatives. Molecules 2017, 22, 952. https://doi.org/10.3390/molecules22060952
Paneth A, Hawrył A, Plech T, Hawrył M, Świeboda R, Janowska D, Wujec M, Paneth P. Lipophilicity Studies on Thiosemicarbazide Derivatives. Molecules. 2017; 22(6):952. https://doi.org/10.3390/molecules22060952
Chicago/Turabian StylePaneth, Agata, Anna Hawrył, Tomasz Plech, Mirosław Hawrył, Ryszard Świeboda, Dominika Janowska, Monika Wujec, and Piotr Paneth. 2017. "Lipophilicity Studies on Thiosemicarbazide Derivatives" Molecules 22, no. 6: 952. https://doi.org/10.3390/molecules22060952