Novel Seleno- and Thio-Urea Containing Dihydropyrrol-2-One Analogues as Antibacterial Agents
Abstract
:1. Introduction
2. Results
2.1. Chemistry
2.2. Quorum-Sensing Inhibition Assay
2.3. Antibacterial Activity
3. Conclusions
4. Materials and Methods
4.1. General Procedure for Synthesis of Selenourea and Thiourea DHP Compounds
4.2. Quorum-Sensing Inhibition Assay
4.3. Analysis of the Minimum Inhibitory and Minimum Bactericidal Concentration of Compounds
4.4. Lysis of Horse Red Blood Cells
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Compound | R1 | R2 | X | Yield (%) |
3a | H | H | Se | 83 |
3b | H | 4-F | Se | 82 |
3c | H | 4-Cl | Se | 85 |
3d | H | 4-Br | Se | 70 |
3e | H | 2-Cl | Se | 84 |
3f | CH3 | 4-Cl | Se | 63 |
3g | H | 2-F | Se | 82 |
3h | H | 4-OCH3 | Se | 80 |
4a | H | H | S | 69 |
4b | H | 4-F | S | 94 |
4c | H | 4-Cl | S | 71 |
4d | H | 4-Br | S | 96 |
4e | H | 2-F | S | 66 |
4f | H | 2-Cl | S | 48 |
4g | H | 3-CF3 | S | 76 |
Compound | P. aeruginosa MH602 | ||
---|---|---|---|
125 µM | 61.5 µM | 31 µM | |
3a | 80 ± 4 | 70 ± 8 | 63 ± 3 |
3b | 67 ± 2 | 43 ± 6 | 38 ± 6 |
3c | 74 ± 2 | 52 ± 3 | 42 ± 4 |
3d | 76 ± 1 | 58 ± 6 | 42 ± 4 |
3e | 81 ± 5 | 65 ± 5 | 53 ± 2 |
3f | 69 ± 6 | 49 ± 6 | 37 ± 3 |
3g | 66 ± 7 | 49 ± 4 | 38 ± 4 |
3h | 80 ± 6 | 64 ± 7 | 53 ± 4 |
4a | 50 ± 1 | 44 ± 0 | 37 ± 1 |
4b | 54 ± 3 | 38 ± 13 | 34 ± 5 |
4c | 70 ± 3 | 48 ± 5 | 35 ± 3 |
4d | 74 ± 2 | 54 ± 5 | 41 ± 5 |
4e | 40 ± 4 | 29 ± 7 | 23 ± 9 |
4f | 63 ± 1 | 55 ± 6 | 49 ± 11 |
4g | 56 ± 2 | 42 ± 2 | 34 ± 3 |
Fu 30 | 96 ± 2 | 91 ± 3 | 93 ± 2 |
Entry | Compounds | MIC/MBC (µM) | |
---|---|---|---|
S. aureus 38 | E. coli K12 | ||
1 | 3a | 31.2 | >250 |
2 | 3b | 125 | NT |
3 | 3c | 15.6/31.2 | >250 |
4 | 3d | >250 | NT |
5 | 3e | 15.6/62.4 | >250 |
6 | 3f | 62.5 | >250 |
7 | 3g | 62.5 | >250 |
8 | 3h | >250 | NT |
9 | 4a | >250 | NT |
10 | 4b | >250 | NT |
11 | 4c | >250 | NT |
12 | 4d | >250 | NT |
13 | 4e | >250 | NT |
14 | 4g | >250 | NT |
15 | 4f | >250 | NT |
16 | Gentamicin | <0.4 | NT |
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Sabir, S.; Yu, T.T.; Kuppusamy, R.; Almohaywi, B.; Iskander, G.; Das, T.; Willcox, M.D.P.; Black, D.S.; Kumar, N. Novel Seleno- and Thio-Urea Containing Dihydropyrrol-2-One Analogues as Antibacterial Agents. Antibiotics 2021, 10, 321. https://doi.org/10.3390/antibiotics10030321
Sabir S, Yu TT, Kuppusamy R, Almohaywi B, Iskander G, Das T, Willcox MDP, Black DS, Kumar N. Novel Seleno- and Thio-Urea Containing Dihydropyrrol-2-One Analogues as Antibacterial Agents. Antibiotics. 2021; 10(3):321. https://doi.org/10.3390/antibiotics10030321
Chicago/Turabian StyleSabir, Shekh, Tsz Tin Yu, Rajesh Kuppusamy, Basmah Almohaywi, George Iskander, Theerthankar Das, Mark D. P. Willcox, David StClair Black, and Naresh Kumar. 2021. "Novel Seleno- and Thio-Urea Containing Dihydropyrrol-2-One Analogues as Antibacterial Agents" Antibiotics 10, no. 3: 321. https://doi.org/10.3390/antibiotics10030321