Synthesis and Antibacterial Activity of New Thiazolidine-2,4-dione-Based Chlorophenylthiosemicarbazone Hybrids
Abstract
:1. Introduction
2. Results and Discussion
2.1. Rationale
2.2. Chemistry
2.3. Antibacterial Screening
2.4. Bactericidal and Bacteriostatic Activity
2.5. Computational Studies
2.6. Cytotoxicity Studies
3. Materials and Methods
3.1. Chemistry
3.1.1. Synthesis of Chlorophenylthiosemicarbazones (17–40)
3.1.2. Synthesis of 4-[(2,5-dioxoimidazolidin-4-ylidene)methyl]-2-methoxyphenyl (2,4-dioxo-1,3-thiazolidin-5-yl/ylidene)acetates (41, 42)
3.2. Microbiology Tests
3.3. Computational Details
3.4. Cytotoxicity Studies
4. Conclusions
Author Contributions
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 17–40 are available from the authors. |
Compound | S. aureus | S. aureus | S. epidermidis | B. subtilis | B. cereus | M. luteus | ||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
ATCC 6538 | ATCC 25923 | ATCC 12228 | ATCC 6633 | ATCC 10876 | ATCC 10240 | |||||||
MIC | MBC | MIC | MBC | MIC | MBC | MIC | MBC | MIC | MBC | MIC | MBC | |
19 | 125 | >1000 | 62.5 | >1000 | 62.5 | >1000 | 62.5 | 500 | 62.5 | >1000 | 62.5 | 1000 |
251.3 | >2010.6 | 125.7 | >2010.6 | 125.7 | >2010.6 | 125.7 | 1005.3 | 125.7 | >2010.6 | 125.7 | 2010.6 | |
20 | 3.91 | 3.91 | 3.91 | 62.5 | 31.25 | 62.5 | 31.25 | 125 | 3.91 | 125 | 7.81 | 125 |
8.4 | 8.4 | 8.4 | 135 | 67.5 | 135 | 67.5 | 270 | 8.4 | 270 | 16.9 | 270 | |
21 | 31.25 | >1000 | 7.81 | 1000 | 31.25 | >1000 | 62.5 | 250 | 31.25 | 250 | 15.63 | 15.63 |
67.5 | >2160.2 | 16.9 | 2160.2 | 67.5 | >2160.2 | 135 | 540 | 67.5 | 540 | 33.8 | 33.8 | |
22 | 15.63 | 1000 | 31.25 | 1000 | 15.63 | 1000 | 31.25 | >1000 | 7.81 | >1000 | 3.91 | 500 |
33.8 | 2160.2 | 67.5 | 2160.2 | 33.8 | 2160.2 | 67.5 | >2160.2 | 16.9 | >2160.2 | 8.4 | 1080.1 | |
23 | 3.91 | >1000 | 3.91 | >1000 | 7.81 | 1000 | 7.81 | 62.5 | 7.81 | >1000 | 7.81 | 7.81 |
7.9 | >2010.6 | 7.9 | >2010.6 | 15.7 | 2010.6 | 15.7 | 125.7 | 15.7 | >2010.6 | 15.7 | 15.7 | |
24 | 125 | >1000 | 62.5 | >1000 | 31.25 | >1000 | 125 | 250 | 62.5 | >1000 | 62.5 | >1000 |
251.3 | >2010.6 | 125.7 | >2010.6 | 62.8 | >2010.6 | 251.3 | 502.6 | 125.7 | >2010.6 | 125.7 | >2010.6 | |
26 | 15.63 | >1000 | 15.63 | >1000 | 31.25 | >1000 | 15.63 | 500 | 62.5 | >1000 | 3.91 | 1000 |
31.7 | >2028.6 | 31.7 | >2028.6 | 63.4 | >2028.6 | 31.7 | 1014.3 | 126.8 | >2028.6 | 7.9 | 2028.6 | |
29 | 125 | >1000 | 62.5 | >1000 | 31.25 | >1000 | 31.25 | 500 | 15.63 | 1000 | 7.81 | 1000 |
237 | >1896.1 | 118.5 | >1896.1 | 59.3 | >1896.1 | 59.3 | 948 | 29.6 | 1896.1 | 14.8 | 1896.1 | |
30 | 7.81 | 250 | 7.81 | 250 | 7.81 | 250 | 7.81 | 250 | 3.91 | 500 | 7.81 | 250 |
16.9 | 542.4 | 16.9 | 542.4 | 16.9 | 542.4 | 16.9 | 542.4 | 8.5 | 1084.8 | 16.9 | 542.4 | |
31 | 7.81 | 500 | 7.81 | 500 | 7.81 | 500 | 7.81 | 500 | 3.91 | 500 | 7.81 | 1000 |
16.9 | 1084.8 | 16.9 | 1084.8 | 16.9 | 1084.8 | 16.9 | 1084.8 | 8.5 | 1084.8 | 16.9 | 2169.6 | |
33 | 15.63 | 1000 | 15.63 | 250 | 31.25 | 500 | 15.63 | 500 | 62.5 | >1000 | 62.5 | >1000 |
33.9 | 2169.6 | 33.9 | 542.4 | 67.8 | 1084.8 | 33.9 | 1084.8 | 135.6 | >2169.6 | 135.6 | >2169.6 | |
34 | 31.25 | 500 | 7.81 | 500 | 15.63 | 500 | 15.63 | 500 | 7.81 | 1000 | 62.5 | 500 |
67.8 | 1084.8 | 16.9 | 1084.8 | 33.9 | 1084.8 | 33.9 | 1084.8 | 16.9 | 2169.6 | 135.6 | 1084.8 | |
35 | 500 | 1000 | 1000 | 500 | 500 | 500 | 500 | 500 | 1000 | 1000 | 1000 | 1000 |
1084.8 | 2169.6 | 2169.6 | 1084.8 | 1084.8 | 1084.8 | 1084.8 | 1084.8 | 2169.6 | 2169.6 | 2169.6 | 2169.6 | |
36 | 125 | 500 | 7.81 | 125 | 7.81 | 62.5 | 250 | 1000 | 7.81 | 1000 | 7.81 | 250 |
252.3 | 1009.4 | 15.8 | 252.3 | 15.8 | 126.2 | 504.7 | 2018.7 | 15.8 | 2018.7 | 15.8 | 504.7 | |
38 | 31.25 | >1000 | 7.81 | >1000 | 7.81 | 250 | 3.91 | 62.5 | 3.91 | 62.5 | 3.91 | 125 |
63.7 | >2036.9 | 15.9 | >2036.9 | 15.9 | 509.2 | 8 | 127.3 | 8 | 127.3 | 8 | 254.6 | |
39 | 250 | 1000 | 250 | 1000 | 500 | 1000 | 500 | 500 | 1000 | 1000 | 1000 | 1000 |
509.2 | 2036.9 | 509.2 | 2036.9 | 1018.5 | 2036.9 | 1018.5 | 1018.5 | 2036.9 | 2036.9 | 2036.9 | 2036.9 | |
40 | 500 | 1000 | 250 | 1000 | 250 | 1000 | 500 | 1000 | 1000 | 1000 | 1000 | 1000 |
951.7 | 1903.4 | 475.8 | 1903.4 | 475.8 | 1903.4 | 951.7 | 1903.4 | 1903.4 | 1903.4 | 1903.4 | 1903.4 | |
Cefuroxime | 0.98 | - | 0.49 | - | 0.24 | - | 15.63 | - | 31.25 | - | 0.98 | - |
2.3 | 1.2 | 0.6 | 36.8 | 73.6 | 2.3 | |||||||
Ciprofloxacin | 0.49 | 0.49 | - | - | 0.49 | 0.49 | 0.015 | 0.12 | 0.12 | 0.12 | 0.98 | 1.95 |
1.5 | 1.5 | 1.5 | 1.5 | 0.05 | 0.4 | 0.4 | 0.4 | 3.0 | 5.9 | |||
Oxacillin | 0.06 | 0.06 | - | - | 0.12 | 0.12 | 0.06 | 0.12 | 62.5 | 62.5 | 0.98 | 0.98 |
0.15 | 0.15 | 0.3 | 0.3 | 0.15 | 0.3 | 155.7 | 155.7 | 2.4 | 2.4 |
Compound | EC70 ± SD (mg/L) (Toxicity Threshold) |
---|---|
20 | 30.82 ± 3.73 |
23 | 21.28 ± 3.84 |
30 | 14.86 ± 1.12 |
31 | 10.94 ± 1.35 |
38 | 19.01 ± 3.80 |
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Trotsko, N.; Kosikowska, U.; Paneth, A.; Plech, T.; Malm, A.; Wujec, M. Synthesis and Antibacterial Activity of New Thiazolidine-2,4-dione-Based Chlorophenylthiosemicarbazone Hybrids. Molecules 2018, 23, 1023. https://doi.org/10.3390/molecules23051023
Trotsko N, Kosikowska U, Paneth A, Plech T, Malm A, Wujec M. Synthesis and Antibacterial Activity of New Thiazolidine-2,4-dione-Based Chlorophenylthiosemicarbazone Hybrids. Molecules. 2018; 23(5):1023. https://doi.org/10.3390/molecules23051023
Chicago/Turabian StyleTrotsko, Nazar, Urszula Kosikowska, Agata Paneth, Tomasz Plech, Anna Malm, and Monika Wujec. 2018. "Synthesis and Antibacterial Activity of New Thiazolidine-2,4-dione-Based Chlorophenylthiosemicarbazone Hybrids" Molecules 23, no. 5: 1023. https://doi.org/10.3390/molecules23051023