Synthesis, Crystal Structures, Lipophilic Properties and Antimicrobial Activity of 5-Pyridylmethylidene-3-rhodanine-carboxyalkyl Acids Derivatives
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Lipophilicity
2.2.1. Lipophilicity Parameters
2.2.2. Lipinski Rule of Five and Veber Rules
- MW (molecular weight) < 500;
- Log p < 5;
- NOHBD (numbers of hydrogen bond donors) < 5;
- NOHBA (numbers of hydrogen bond acceptors) < 10.
- number of rotable bonds (NORB) < 14;
- total polar surface area (TPSA) < 140 Å2.
2.2.3. Bioactivity
2.3. Crystal and Molecular Structures of / 4a /, / 5a / and / 3c /
2.4. Antimicrobial Activity
3. Experimental Sections
3.1. Materials and Methods
3.2. General Procedure of Knoevenagel Condensation of Rhodanine 3-Alcanoic Acids with Aldehydes
3.3. Antimicrobial Activity In Vitro Assay
3.4. Determination of Lipophilicity Parameters
3.5. X-ray Analysis
3.6. Computational Details
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Compound | D-H···A | H···A [Å] | D···A [Å] | D-H···A [°] | Symmetry Codes |
---|---|---|---|---|---|
/4a/ | O3-H3···N1 | 1.84 | 2.622 | 163.4 | −x − 2, −y + 1, −z + 2 |
C6-H6···O1 | 2.62 | 3.533 | 161.5 | −x − 2, −y + 1, −z + 2 | |
C11-H11···S2 | 2.90 | 3.572 | 128.7 | −x, −y, −z + 2 | |
C14-H14A···O2 | 2.33 | 3.269 | 159.0 | x + 1, y, z | |
C14-H14B···O2 | 2.65 | 3.452 | 137.9 | −x − 1, −y + 1, −z + 1 | |
/5a/ | O3-H3···N1 | 1.76 | 2.649 | 169.9 | −x + 1, −y + 1, −z + 1 |
C6-H6···O2 | 2.52 | 3.380 | 153.6 | −x + 1, y − 1/2, −z + 3/2 | |
C9-H9···S2 | 2.96 | 3.761 | 144.9 | x + 1, y, z | |
C10-H10···O1 | 2.47 | 3.285 | 147.1 | x, −y + 1/2, z − 1/2 | |
C12-H12B···O3 | 2.63 | 3.462 | 144.3 | −x, y − 1/2, −z + 3/2 | |
C14-H14B···S2 | 2.91 | 3.843 | 162.2 | x, −y + 1/2, z + 1/2 | |
/3c/ | O3-H3···O2 | 1.77 | 2.681 | 172.7 | −x + 2, −y − 1, −z |
C6-H6···O1 | 2.30 | 3.210 | 160.7 | −x + 2, −y, −z + 1 | |
C11-H11···S1 | 2.78 | 3.592 | 143.4 | −x + 1, −y + 1, −z + 1 | |
C15-H15A···S2 | 2.80 | 3.63 | 141.3 | −x, −y, −z |
Compound | N-S Distance [Å] | Electron Density at BCP [a.u.] | Charge N | Charge S | Force Constant |
---|---|---|---|---|---|
3a | 2.8551 | 0.0180 | −1.1503 | 0.3120 | 0.1517 |
3b | 2.8574 | 0.0179 | −1.1504 | 0.3084 | 0.1512 |
3c | 2.8563 | 0.0179 | −1.1503 | 0.3095 | 0.1515 |
3d | 2.8582 | 0.0179 | −1.1502 | 0.3076 | 0.1511 |
Microorganism | 3a | 3b | 3c | 3d | 4a | 4b | 4c | 4d | 5a | 5b | 5c | 5d |
---|---|---|---|---|---|---|---|---|---|---|---|---|
S. aureus ATCC 25923 | 62.5 | 62.5 | 62.5 | 62.5 | 250 | 250 | 250 | 500 | 500 | 250 | 125 | 250 |
S. aureus ATCC 6538 | 125 | 62.5 | 62.5 | 62.5 | 250 | 250 | 250 | 500 | 500 | 250 | 125 | 250 |
S. aureus ATCC 43300 | 62.5 | 125 | 62.5 | 62.5 | 250 | 250 | 250 | 250 | 500 | 250 | 125 | 250 |
S. epidermidis ATCC 12228 | 125 | 62.5 | 62.5 | 31.3 | 250 | 125 | 125 | 250 | 125 | 125 | 125 | 125 |
M. luteus ATCC 10240 | 125 | 62.5 | 125 | 7.8 | 250 | 15.6 | 31.3 | 31.3 | 125 | 7.8 | 31.3 | 7.8 |
B. subtilis ATCC 6633 | 62.5 | 62.5 | 31.3 | 125 | 250 | 250 | 125 | 500 | 500 | >1000 | 125 | 500 |
B. cereus ATCC 10876 | 125 | 62.5 | 31.3 | 62.5 | 250 | 125 | 125 | 62.5 | 250 | >1000 | 62.5 | 125 |
S. pyogenes ATCC 19615 | 500 | >1000 | >1000 | 1000 | >1000 | 500 | >1000 | >1000 | 500 | 500 | 250 | 1000 |
S. pneumoniae ATCC 49619 | 1000 | >1000 | >1000 | >1000 | >1000 | 500 | >1000 | >1000 | 1000 | >1000 | 1000 | >1000 |
S. mutans ATCC 25175 | 500 | >1000 | >1000 | >1000 | >1000 | >1000 | >1000 | >1000 | 1000 | >1000 | >1000 | >1000 |
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Żesławska, E.; Zakrzewski, R.; Nowicki, A.; Korona-Głowniak, I.; Lyčka, A.; Kania, A.; Zborowski, K.K.; Suder, P.; Skórska-Stania, A.; Tejchman, W. Synthesis, Crystal Structures, Lipophilic Properties and Antimicrobial Activity of 5-Pyridylmethylidene-3-rhodanine-carboxyalkyl Acids Derivatives. Molecules 2022, 27, 3975. https://doi.org/10.3390/molecules27133975
Żesławska E, Zakrzewski R, Nowicki A, Korona-Głowniak I, Lyčka A, Kania A, Zborowski KK, Suder P, Skórska-Stania A, Tejchman W. Synthesis, Crystal Structures, Lipophilic Properties and Antimicrobial Activity of 5-Pyridylmethylidene-3-rhodanine-carboxyalkyl Acids Derivatives. Molecules. 2022; 27(13):3975. https://doi.org/10.3390/molecules27133975
Chicago/Turabian StyleŻesławska, Ewa, Robert Zakrzewski, Arkadiusz Nowicki, Izabela Korona-Głowniak, Antonín Lyčka, Agnieszka Kania, Krzysztof Kazimierz Zborowski, Piotr Suder, Agnieszka Skórska-Stania, and Waldemar Tejchman. 2022. "Synthesis, Crystal Structures, Lipophilic Properties and Antimicrobial Activity of 5-Pyridylmethylidene-3-rhodanine-carboxyalkyl Acids Derivatives" Molecules 27, no. 13: 3975. https://doi.org/10.3390/molecules27133975