Evaluation of the Lipophilicity of Angularly Condensed Diquino- and Quinonaphthothiazines as Potential Candidates for New Drugs
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. Materials
3.2. Chromatographic Procedure
3.3. Computational Programs
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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No. of Compound | Chemical Structure | No. of Compound | Chemical Structure | No. of Compound | Chemical Structure |
---|---|---|---|---|---|
1 | 8 | 15 | |||
2 | 9 | 16 | |||
3 | 10 | 17 | |||
4 | 11 | 18 | |||
5 | 12 | 19 | |||
6 | 13 | 20 | |||
7 | 14 | 21 |
No. of Compound | ALOGPs | AClogP | ALOGP | MLOGP | XLOGP2 | XLOGP3 | LogP * | ClogP ** |
---|---|---|---|---|---|---|---|---|
1 | 4.90 | 4.66 | 4.58 | 2.78 | 4.72 | 4.48 | 4.54 | 5.23 |
2 | 4.61 | 5.37 | 4.79 | 3.01 | 5.02 | 4.62 | 4.92 | 5.09 |
3 | 5.06 | 5.97 | 5.40 | 3.39 | 5.64 | 5.26 | 5.35 | 5.86 |
4 | 4.87 | 5.26 | 5.98 | 3.39 | 5.29 | 4.73 | 4.77 | 5.51 |
5 | 4.93 | 4.66 | 4.58 | 3.17 | 4.72 | 4.48 | 4.54 | 5.13 |
6 | 4.64 | 5.37 | 4.79 | 3.40 | 5.02 | 4.62 | 4.92 | 5.03 |
7 | 5.06 | 5.97 | 5.40 | 3.78 | 5.64 | 5.26 | 5.35 | 5.80 |
8 | 4.91 | 5.26 | 5.98 | 3.78 | 5.29 | 4.73 | 4.77 | 5.48 |
9 | 4.92 | 4.66 | 5.58 | 3.17 | 4.72 | 4.48 | 4.41 | 5.13 |
10 | 4.64 | 5.37 | 4.79 | 3.40 | 5.02 | 4.64 | 4.92 | 5.03 |
11 | 4.93 | 4.66 | 4.58 | 3.17 | 4.72 | 4.48 | 4.87 | 5.13 |
12 | 4.59 | 5.37 | 4.79 | 3.40 | 5.02 | 4.62 | 4.92 | 5.03 |
13 | 5.04 | 5.97 | 5.40 | 3.78 | 5.64 | 5.26 | 5.35 | 5.80 |
14 | 5.87 | 5.53 | 5.30 | 4.24 | 5.88 | 5.46 | 5.63 | 6.12 |
15 | 5.54 | 6.24 | 5.51 | 4.47 | 6.19 | 5.60 | 5.80 | 6.12 |
16 | 6.10 | 6.84 | 6.13 | 4.83 | 6.80 | 6.24 | 6.28 | 6.90 |
17 | 5.63 | 6.13 | 6.70 | 4.83 | 6.45 | 5.72 | 5.98 | 6.54 |
18 | 5.85 | 5.53 | 5.30 | 4.24 | 5.88 | 5.46 | 5.63 | 6.11 |
19 | 5.54 | 6.24 | 5.51 | 4.47 | 6.19 | 5.60 | 5.80 | 6.12 |
20 | 6.05 | 6.84 | 6.13 | 4.83 | 6.80 | 6.24 | 6.28 | 6.90 |
21 | 5.60 | 6.13 | 6.70 | 4.83 | 6.45 | 5.72 | 5.98 | 6.54 |
No. of Compound | RM0 | r | b | LogPTLC |
---|---|---|---|---|
1 | 3.15 | 0.9953 | −0.0383 | 4.26 |
2 | 4.14 | 0.9954 | −0.0503 | 5.57 |
3 | 4.30 | 0.9944 | −0.058 | 5.77 |
4 | 3.35 | 0.9953 | −0.0383 | 4.56 |
5 | 3.72 | 0.9927 | −0.0459 | 5.03 |
6 | 4.24 | 0.9982 | −0.0582 | 5.69 |
7 | 4.46 | 0.9988 | −0.0534 | 5.97 |
8 | 3.96 | 0.9987 | −0.0539 | 5.34 |
9 | 3.69 | 0.9969 | −0.0498 | 4.99 |
10 | 4.37 | 0.9977 | −0.0540 | 5.86 |
11 | 3.48 | 0.9960 | −0.0462 | 4.72 |
12 | 4.21 | 0.9989 | −0.0576 | 5.65 |
13 | 3.58 | 0.9928 | −0.0478 | 4.85 |
14 | 4.24 | 0.9967 | −0.0573 | 5.69 |
15 | 4.49 | 0.9965 | −0.0527 | 6.01 |
16 | 4.60 | 0.9979 | −0.0571 | 6.15 |
17 | 4.29 | 0.9985 | −0.0529 | 5.76 |
18 | 3.81 | 0.9934 | −0.0484 | 5.14 |
19 | 4.18 | 0.9931 | −0.0538 | 5.58 |
20 | 4.34 | 0.9973 | −0.0548 | 5.82 |
21 | 4.09 | 0.9977 | −0.0507 | 5.50 |
Lipophilicity Parameter | Standard | ||||
---|---|---|---|---|---|
I | II | III | IV | V | |
logPlit | 1.21 [36] | 1.87 [37] | 3.18 [37] | 4.45 [37] | 6.38 [38] |
RM0 | 0.78 | 1.16 | 2.51 | 3.33 | 4.69 |
-b | 0.0162 | 0.0247 | 0.0328 | 0.0412 | 0.0564 |
r | 0.992 | 0.994 | 0.997 | 0.998 | 0.998 |
logPTLC | 1.21 | 1.70 | 3.43 | 4.49 | 6.24 |
No. of Compound | Caco-2 [10−6 cm/s] | PPB [%] | CNS | HIA [%] | P-gp Substrates | CYP1A2 Inhibitor | CYP2C9 Inhibitor | CYP2C19 Inhibitor | CYP2D6 Inhibitor | CYP3A4 Inhibitor |
---|---|---|---|---|---|---|---|---|---|---|
1 | 226 | 99 | −3.30 | 100 | 0.30 | 0.61 | 0.34 | 0.49 | 0.48 | 0.53 |
2 | 231 | 99 | −3.23 | 100 | 0.38 | 0.57 | 0.26 | 0.49 | 0.46 | 0.50 |
3 | 207 | 100 | −3.44 | 100 | 0.35 | 0.62 | 0.33 | 0.52 | 0.48 | 0.53 |
4 | 235 | 100 | −3.96 | 100 | 0.35 | 0.68 | 0.40 | 0.51 | 0.42 | 0.54 |
5 | 226 | 99 | −3.30 | 100 | 0.30 | 0.58 | 0.34 | 0.50 | 0.48 | 0.58 |
6 | 231 | 99 | −3.23 | 100 | 0.38 | 0.61 | 0.26 | 0.49 | 0.46 | 0.54 |
7 | 207 | 100 | −3.44 | 100 | 0.35 | 0.55 | 0.33 | 0.51 | 0.48 | 0.53 |
8 | 235 | 100 | −3.96 | 100 | 0.35 | 0.67 | 0.40 | 0.50 | 0.37 | 0.54 |
9 | 230 | 99 | −3.30 | 100 | 0.30 | 0.58 | 0.34 | 0.50 | 0.48 | 0.58 |
10 | 231 | 99 | −3.23 | 100 | 0.38 | 0.61 | 0.26 | 0.49 | 0.46 | 0.54 |
11 | 211 | 99 | −3.30 | 100 | 0.30 | 0.58 | 0.34 | 0.50 | 0.48 | 0.58 |
12 | 231 | 99 | −3.23 | 100 | 0.38 | 0.61 | 0.26 | 0.49 | 0.46 | 0.54 |
13 | 207 | 100 | −3.44 | 100 | 0.35 | 0.55 | 0.33 | 0.51 | 0.48 | 0.53 |
14 | 131 | 100 | −3.51 | 100 | 0.28 | 0.66 | 0.33 | 0.51 | 0.49 | 0.53 |
15 | 163 | 100 | −3.40 | 100 | 0.38 | 0.68 | 0.26 | 0.53 | 0.47 | 0.50 |
16 | 94 | 100 | −3.72 | 100 | 0.38 | 0.63 | 0.32 | 0.57 | 0.50 | 0.51 |
17 | 137 | 100 | −4.30 | 100 | 0.34 | 0.71 | 0.39 | 0.53 | 0.43 | 0.56 |
18 | 131 | 100 | −3.51 | 100 | 0.28 | 0.66 | 0.33 | 0.51 | 0.49 | 0.53 |
19 | 163 | 100 | −3.40 | 100 | 0.38 | 0.68 | 0.26 | 0.53 | 0.47 | 0.50 |
20 | 94 | 100 | −3.72 | 100 | 0.38 | 0.63 | 0.32 | 0.57 | 0.50 | 0.51 |
21 | 137 | 100 | −4.30 | 100 | 0.34 | 0.71 | 0.39 | 0.53 | 0.43 | 0.56 |
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Klimoszek, D.; Jeleń, M.; Morak-Młodawska, B.; Dołowy, M. Evaluation of the Lipophilicity of Angularly Condensed Diquino- and Quinonaphthothiazines as Potential Candidates for New Drugs. Molecules 2024, 29, 1683. https://doi.org/10.3390/molecules29071683
Klimoszek D, Jeleń M, Morak-Młodawska B, Dołowy M. Evaluation of the Lipophilicity of Angularly Condensed Diquino- and Quinonaphthothiazines as Potential Candidates for New Drugs. Molecules. 2024; 29(7):1683. https://doi.org/10.3390/molecules29071683
Chicago/Turabian StyleKlimoszek, Daria, Małgorzata Jeleń, Beata Morak-Młodawska, and Małgorzata Dołowy. 2024. "Evaluation of the Lipophilicity of Angularly Condensed Diquino- and Quinonaphthothiazines as Potential Candidates for New Drugs" Molecules 29, no. 7: 1683. https://doi.org/10.3390/molecules29071683