5-Benzyliden-2-(5-methylthiazol-2-ylimino)thiazolidin-4-ones as Antimicrobial Agents. Design, Synthesis, Biological Evaluation and Molecular Docking Studies
Abstract
:1. Introduction
2. Results and Discussion
2.1. Toxicity Prediction
2.2. Chemistry
2.3. Biological Evaluation
2.3.1. Antibacterial Action
2.3.2. Antifungal Activity
2.4. Docking Studies
2.4.1. Docking in E. coli-MurB
2.4.2. Docking in Antifungal Targets
2.5. Cellular Toxicity
3. Materials and Methods
3.1. Chemistry
3.1.1. Synthesis of 5-Methylthiazol-2-yl chloroacetamide
3.1.2. Synthesis of 2-(5-Methylthiazol-2-yl) thiazolidin-4-one
3.1.3. General Procedure for the Synthesis of 5-Benzyliden-2-(5-methylthiazol-2-ylimino) thiazolidin-4-one
5-benzyliden -2-(5-methylthaizol-2-ylimino) thiazolidin-4-one (1)
2-(5-methylthiazol-2-ylimino)-5-(2-hydroxybenzyliden) thiazolidin-4-one (2)
2-(5-methylthiazol-2-ylimino)-5-(4-hydroxybenzyliden) thiazolidin-4-one (3)
2-(5-methylthiazol-2-ylimino)-5-(4-methoxybenzyliden) thiazolidin-4-one (4)
2-(5-methylthiazol-2-ylimino)-5-(2,5-dimethoxybenzyliden) thiazolidin-4-one (5)
2-(5-methylthiazol-2-ylimino)-5-(2-nitrobenzyliden) thiazolidin-4-one (6)
2-(5-methylthiazol-2-ylimino)-5-(3-nitrobenzyliden) thiazolidin-4-one (7)
2-(5-methylthiazol-2-ylimino)-5-(3-fluorobenzyliden) thiazolidin-4-one (8)
2-(5-methylthiazol-2-ylimino)-5-(4-fluorobenzyliden) thiazolidin-4-one (9)
2-(5-methylthiazol-2-ylimino)-5-(4-chlorobenzyliden) thiazolidin-4-one (10)
2-(5-methylthiazol-2-ylimino)-5-(2,3-dichlorobenzyliden) thiazolidin-4-one (11)
2-(5-methylthiazol-2-ylimino)-5-(2,4-dichlorobenzyliden) thiazolidin-4-one (12)
2-(5-methylthiazol-2-ylimino)-5-(2,6-dichlorobenzyliden) thiazolidin-4-one (13)
2-(5-methylthiazol-2-ylimino)-5-(3-bromobenzyliden) thiazolidin-4-one (14)
2-(5-methylthiazol-2-ylimino)-5-(4-bromobenzyliden) thiazolidin-4-one (15)
3.2. Biological Evaluation
3.2.1. Antibacterial Action
3.2.2. Methicillin-resistant Staphylococcus aureus (MRSA)
3.2.3. E. coli
3.2.4. Pseudomonas aeruginosa
3.2.5. Inhibition of Biofilm Formation
3.2.6. Antifungal Activity
3.3. Statistical Analysis
3.4. Cytotoxicity
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Compounds | R | MIC/MBC | B.c. | S.a. | M.f. | L.m. | P.a. | En.cl. | E.c. | S.t. |
---|---|---|---|---|---|---|---|---|---|---|
1 | H | MIC | 33.2 ± 0.03 | 265.8 ± 0.03 | 265.8 ± 0.04 | 265.8 ± 0.06 | 265.8 ± 0.08 | 265.8 ± 0.03 | 33.2 ± 0.01 | 265.8 ± 0.05 |
MBC | 66.4 ± 0.02 | 531.6 ± 0.4 | 531.6 ± 0.6 | 531.6 ± 0.3 | 531.6 ± 0.5 | 531.6 ± 0.5 | 66.4 ± 0.03 | 531.6 ± 0.3 | ||
2 | 2-OH | MIC | 94.6 ± 0.03 | 94.6 ± 0.05 | 94.6 ± 0.02 | 94.6 ± 0.01 | 94.6 ± 0.03 | 94.6 ± 0.03 | 94.6 ± 0.03 | 94.6 ± 0.02 |
MBC | 189.2 ± 005 | 189.2 ± 0.08 | 189.2 ± 0.01 | 189.2 ± 0.05 | 189.2 ± 0.02 | 189.2 ± 0.04 | 189.2 ± 0.04 | 189.2 ± 0.03 | ||
3 | 4-OH | MIC | 63.0 ± 003 | 126.1 ± 0.06 | 189.2 ± 0.02 | 126.1 ± 0.04 | 378.5 ± 0.8 | 126.1 ± 0.05 | 63.0 ± 0.02 | 126.1 ± 0.02 |
MBC | 126.1 ± 0.03 | 252.3 ± 0.05 | 378.5 ± 0.6 | 252.3 ± 0.03 | 757.0 ± 0.8 | 252.3 ± 0.05 | 126.1 ± 0.03 | 252.3 ± 0.03 | ||
4 | 4-OCH3 | MIC | 30.2 ± 0.04 | 120.8 ± 0.05 | 120.8 ± 0.03 | 120.8 ± 0.05 | 261.6 ± 0.05 | 120.8 ± 0.06 | 30.2 ± 0.01 | 120.8 ± 0.05 |
MBC | 60.4 ± 006 | 241.6 ± 0.06 | 241.6 ± 0.02 | 241.6 ± 0.06 | 483.3 ± 0.6 | 241.6 ± 0.06 | 60.4 ± 0.04 | 241.6 ± 0.04 | ||
5 | 2,5-di-OCH3 | MIC | 96.9 ± 0.06 | 193.9 ± 0.05 | 193.9 ± 0.03 | 193.9 ± 0.04 | 193.9 ± 0.06 | 96.9 ± 0.04 | 193.9 ± 0.03 | 193.9 ± 0.03 |
MBC | 193.9 ± 0.05 | 387.8 ± 0.3 | 387.8 ± 0.4 | 387.8 ± 0.3 | 387.8 ± 0.4 | 193.9 ± 0.08 | 387.8 ± 0.4 | 387.8 ± 0.4 | ||
6 | 2-NO2 | MIC | 57.8 ± 0.03 | 115.6 ± 0.04 | 231.2 ± 0.08 | 115.6 ± 0.03 | 115.6 ± 0.05 | 115.6 ± 0.04 | 115.6 ± 0.04 | 231.2 ± 0.06 |
MBC | 115.6 ± 0.03 | 115.6 ± 0.03 | 462.4 ± 0.03 | 231.2 ± 0.02 | 231.2 ± 0.08 | 231.2 ± 0.04 | 231.2 ± 0.05 | 462.4 ± 0.4 | ||
7 | 3-NO2 | MIC | 86.7 ± 0.02 | 86.7 ± 0.02 | 86.7 ± 0.02 | 86.7 ± 0.02 | 86.7 ± 0.05 | 43.3 ± 0.03 | 43.3 ± 0.03 | 86.7 ± 0.05 |
MBC | 173.4 ± 0.01 | 173.4 ± 0.06 | 173.4 ± 0.04 | 173.4 ± 0.03 | 173.4 ± 0.03 | 86.7 ± 0.02 | 86.7 ± 0.02 | 173.4 ± 0.06 | ||
8 | 3-F | MIC | 125.4 ± 0.03 | 125.4 ± 0.08 | 125.4 ± 0.04 | 125.4 ± 0.04 | 125.4 ± 0.04 | 62.7 ± 0.01 | 62.7 ± 0.01 | 125.4 ± 0.06 |
MBC | 250.8 ± 0.06 | 250.8 ± 0.06 | 250.8 ± 0.06 | 250.8 ± 0.06 | 250.7 ± 0.05 | 125.4 ± 0.03 | 125.4 ± 0.03 | 250.8 ± 0.08 | ||
9 | 4-F | MIC | 344.8 ± 0.5 | 344.8 ± 0.3 | 344.8 ± 0.2 | 344.8 ± 0.3 | 344.8 ± 0.6 | 125.4 ± 0.05 | 125.4 ± 0.03 | 344.8 ± 0.4 |
MBC | 689.6 ± 0.8 | 689.6 ± 0.6 | 689.6 ± 0.3 | 689.6 ± 0.8 | 689.6 ± 0.8 | 250.7 ± 0.07 | 250.7 ± 0.03 | 689.6 ± 0.6 | ||
10 | 4-Cl | MIC | 26.3 ± 0.01 | 89.4 ± 0.03 | 178.8 ± 0.04 | 89.4 ± 0.07 | 357.6 ± 0.4 | 178.8 ± 0.03 | 26.3 ± 0.02 | 357.6 ± 0.6 |
MBC | 52.6 ± 0.01 | 178.8 ± 0.02 | 357.6 ± 0.3 | 178.8 ± 0.08 | 715.3 ± 0.8 | 357.6 ± 0.4 | 52.6 ± 0.03 | 715.3 ± 0.8 | ||
11 | 2,3-di-Cl | MIC | 189.2 ± 0.06 | 189.2 ± 0.06 | 189.2 ± 0.05 | 189.2 ± 0.06 | 189.2 ± 0.06 | 94.6 ± 0.02 | 94.6 ± 0.05 | 189.2 ± 0.05 |
MBC | 378.4 ± 0.5 | 378.4 ± 0.6 | 378.4 ± 0.06 | 378.4 ± 0.8 | 378.4 ± 0.5 | 189.2 ± 0.03 | 189.2 ± 0.04 | 378.4 ± 0.3 | ||
12 | 2,4-di-Cl | MIC | 135.1 ± 0.03 | 135.1 ± 0.05 | 135.1 ± 0.04 | 270.2 ± 0.4 | 270.2 ± 0.3 | 270.2 ± 0.4 | 135.1 ± 0.02 | 270.2 ± 0.3 |
MBC | 270.2 ± 0.3 | 270.2 ± 0.4 | 270.2 ± 0.4 | 540.5 ± 0.5 | 540.5 ± 0.4 | 540.5 ± 0.6 | 270.2 ± 0.3 | 540.5 ± 0.8 | ||
13 | 2,6-di-Cl | MIC | 40.5 ± 0,004 | 81.0 ± 0.06 | 81.0 ± 0.03 | 81.0 ± 0.05 | 162.1 ± 0.05 | 162.1 ± 0.05 | 81.0 ± 0.03 | 162.1 ± 0.05 |
MBC | 81.0 ± 0.06 | 324.2 ± 0.4 | 162.1 ± 0.02 | 162.1 ± 0.06 | 324.2 ± 0.5 | 324.2 ± 0.3 | 162.1 ± 0.04 | 324.2 ± 0.5 | ||
14 | 3-Br | MIC | 78.9 ± 0.06 | 78.9 ± 0.05 | 78.9 ± 0.03 | 78.9 ± 0.06 | 157.9 ± 0.07 | 78.9 ± 0.03 | 78.9 ± 0.05 | 157.9 ± 0.05 |
MBC | 157.9 ± 0.05 | 157.9 ± 0.04 | 157.9 ± 0.05 | 157.9 ± 0.05 | 315.8 ± 0.5 | 157.9 ± 0.04 | 157.9 ± 0.06 | 315.8 ± 0.3 | ||
15 | 4-Br | MIC | 78.9 ± 0.01 | 342.1 ± 0.5 | 342.1 ± 0.3 | 342.1 ± 0.5 | 342.1 ± 0.6 | 342.1 ± 0.6 | 78.9 ± 0.03 | 342.1 ± 0.4 |
MBC | 157.9 ± 0.05 | 684.2 ± 0.8 | 684.2 ± 0.8 | 684.2 ± 0.8 | 684.2 ± 0.8 | 684.2 ± 0.8 | 157.9 ± 0.04 | 684.2 ± 0.9 | ||
STM | MIC | 43.0 ± 0.04 | 172 ± 0.3 | 86 ± 0.02 | 258 ± 0.4 | 172 ± 0.3 | 43 ± 0.04 | 172 ± 0.3 | 172 ± 0.3 | |
MBC | 86 ± 0.05 | 344 ± 0.5 | 172 ± 0.3 | 516 ± 0.5 | 344 ± 0.4 | 86 ± 0.05 | 344 ± 0.4 | 344 ± 0.4 | ||
AMP | MIC | 248 ± 0.3 | 248 ± 0.4 | 248 ± 0.3 | 372 ± 0.3 | 744 ± 0.6 | 248 ± 0.6 | 372 ± 0.4 | 248 ± 0.4 | |
MBC | 372 ± 0.4 | 372 ± 0.5 | 372 ± 0.6 | 744 ± 0.6 | 1240 ± 0.8 | 372 ± 0.4 | 492 ± 0.6 | 492 ± 0.3 |
Νο. | MIC/MBC | MRSA | P.a. | E.c. |
---|---|---|---|---|
1 | MIC | 255.7 ± 0.04 | 122.8 ± 0.1 | 33.2 ± 0.03 |
MBC | 531.5 ± 0.08 | 265 ± 0.3 | 66.4 ± 0.02 | |
2 | MIC | 173.4 ± 0.05 | 173.4 ± 0.05 | 173.4 ± 0.04 |
MBC | 346.8 ± 0.03 | 346.8 ± 0.4 | 346.8 ± 0.10 | |
3 | MIC | 189.2 ± 0.2 | 189.2 ± 0.4 | 31.5 ± 0.05 |
MBC | 378.5 ± 0.03 | 378.5 ± 0.02 | 63.0 ± 0.04 | |
4 | MIC | 120.8 ± 0.08 | 120.8 ± 0.3 | 60.4 ± 0.04 |
MBC | 241.6 ± 0.02 | 241.6 ± 0.03 | 120.8 ± 0.05 | |
5 | MIC | 193.9 ± 0.06 | 96.9 ± 0.10 | 96.9 ± 0.02 |
MBC | 387.8 ± 0.03 | 193.9 ± 0.5 | 193.9 ± 0.04 | |
6 | MIC | 433.5 ± 0.06 | 433.5 ± 0.03 | 433.5 ± 0.4 |
MBC | 867.0 ± 0.02 | 867.0 ± 0.3 | 867.0 ± 0.10 | |
7 | MIC | 289.0 ± 0.03 | 144.5 ± 0.06 | 144.5 ± 0.02 |
MBC | 578.0 ± 0.04 | 289.0 ± 0.03 | 289.0 ± 0.4 | |
8 | MIC | 125.4 ± 0.02 | 125.4 ± 0.08 | 125.4 ± 0.05 |
MBC | 250.8 ± 0.03 | 250.8 ± 0.01 | 250.8 ± 0.06 | |
9 | MIC | 219.4 ± 0.08 | 219.4 ± 0.3 | 219.4 ± 0.04 |
MBC | 438.8 ± 0.03 | 438.8 ± 0.10 | 438.8 ± 0.02 | |
10 | MIC | 178.8 ± 0.06 | 89.4 ± 0.03 | 29.8 ± 0.02 |
MBC | 357.6 ± 0.05 | 178.8 ± 0.02 | 59.6 ± 0.10 | |
11 | MIC | 189.2 ± 0.06 | 189.2 ± 0.5 | 189.2 ± 0.03 |
MBC | 378.4 ± 0.04 | 378.4 ± 0.03 | 378.4 ± 0.02 | |
12 | MIC | 135.1 ± 0.08 | 67.5 ± 0.09 | 67.5 ± 0.06 |
MBC | 270.2 ± 0.06 | 135.1 ± 0.3 | 135.1 ± 0.4 | |
13 | MIC | 270.2 ± 0.05 | 135.1 ± 0.3 | 135.1 ± 0.02 |
MBC | 540.5 ± 0.06 | 270.2 ± 0.5 | 270.2 ± 0.03 | |
14 | MIC | 131.6 ± 0.04 | 131.6 ± 0.06 | 263.2 ± 0.06 |
MBC | 263.2 ± 0.02 | 263.2 ± 0.04 | 526.4 ± 0.02 | |
15 | MIC | 157.9 ± 0.03 | 78.9 ± 0.02 | 78.9 ± 0.01 |
MBC | 215.8 ± 0.04 | 157.9 ± 0.10 | 157.9 ± 0.05 | |
Streptomycin | MIC | 171.9 ± 0.02 | 86 ± 0.3 | 171.9 ± 0.06 |
MBC | / | 171.9 ± 0.03 | 343 ± 0.02 | |
Ampicillin | MIC | / | 572 ± 0.6 | 572 ± 0.4 |
MBC | / | / | / |
Compound | MIC | 0.5 MIC |
---|---|---|
2 | 9.89 | 15.33 |
7 | 36.64 | NE |
8 | 61.34 | 48.67 |
13 | 62.69 | 35.49 |
14 | 56.74 | 40.54 |
Ampicillin | 71.94 | 55.42 |
Streptomycin | 67.36 | 30.35 |
Νο. | MIC/MFC | A.v. | T.v. | A.o. | A.n. | P.v.c. | P.f. | P.o. | A.fum. |
---|---|---|---|---|---|---|---|---|---|
1 | MIC | 265.8 ± 0.2 | 132.9 ± 0.08 | 265.8 ± 0.2 | 265.8 ± 0.05 | 132.9 ± 0.2 | 265.8 ± 0.1 | 265.8 ± 0.2 | 265.8 ± 0.02 |
MFC | 531.6 ± 0.3 | 265.8 ± 0.3 | 531.6 ± 0.4 | 531.6 ± 0.03 | 265.8 ± 0.3 | 531.6 ± 0.2 | 531.6 ± 0.3 | 531.6 ± 0.03 | |
2 | MIC | 441.6 ± 0.2 | 220.8 ± 0.06 | 220.8 ± 0.5 | 220.8 ± 0.08 | 220.8 ± 0.08 | 220.8 ± 0.03 | 630.9 ± 0.4 | 220.8 ± 0.05 |
MFC | 883.2 ± 0.4 | 441.6 ± 0.2 | 441.6 ± 0.3 | 441.6 ± 0.06 | 441.6 ± 0.3 | 441.6 ± 0.2 | 883.2 ± 0.4 | 441.6 ± 0.06 | |
3 | MIC | 94.6 ± 0.4 | 94.6 ± 0.05 | 94.6 ± 0.1 | 189.2 ± 0.09 | 94.6 ± 0.4 | 189.2 ± 0.3 | 94.6 ± 0.4 | 94.6 ± 0.04 |
MFC | 189.2 ± 0.2 | 189.2 ± 0.3 | 189.2 ± 0.4 | 378.4 ± 0.10 | 189.2 ± 0.5 | 378.4 ± 0.3 | 189.2 ± 0.3 | 94.6 ± 0.08 | |
4 | MIC | 120.8 ± 0.5 | 60.4 ± 0.02 | 120.8 ± 0.3 | 241.6 ± 0.03 | 120.8 ± 0.05 | 120.8 ± 0.06 | 60.4 ± 0.1 | 120.8 ± 0.05 |
MFC | 241.6 ± 0.3 | 120.8 ± 0.4 | 241.6 ± 0.2 | 483.2 ± 0.06 | 241.6 ± 0.02 | 241.6 ± 0.06 | 120.8 ± 0.02 | 241.6 ± 0.03 | |
5 | MIC | 110.8 ± 0.4 | 27.7 ± 0.02 | 55.4 ± 0.3 | 110.8 ± 0.01 | 110.8 ± 0.05 | 110.8 ± 0.08 | 110.8 ± 0.04 | 110.8 ± 0.03 |
MFC | 221.6 ± 0.5 | 55.4 ± 0.03 | 118 ± 0.4 | 221.6 ± 0.03 | 221.6 ± 0.06 | 221.6 ± 0.02 | 221.6 ± 0.04 | 221.6 ± 0.05 | |
6 | MIC | 289.0 ± 0.3 | 144.5 ± 0.05 | 289.0 ± 0.5 | 115.6 ± 0.03 | 115.6 ± 0.06 | 115.6 ± 0.05 | 289.0 ± 0.2 | 231.2 ± 0.002 |
MFC | 578.0 ± 0.4 | 289.0 ± 0.3 | 578.0 ± 0.3 | 231.2 ± 0.05 | 231.2 ± 0.03 | 231.2 ± 0.06 | 289.0 ± 0.4 | 462.4 ± 0.03 | |
7 | MIC | 578.0 ± 0.3 | 289.0 ± 0.2 | 289.0 ± 0.5 | 72.2 ± 0.04 | 72.2 ± 0.6 | 34.6 ± 0.08 | 578.0 ± 0.2 | 72.2 ± 0.03 |
MFC | 1156 ± 0.3 | 578.0 ± 0.3 | 578.0 ± 0.2 | 144.4 ± 0.06 | 144.4 ± 0.06 | 72.2 ± 0.06 | 1156.0 ± 0.5 | 144.4 ± 0.04 | |
8 | MIC | 156.7 ± 0.6 | 156.7 ± 0.08 | 313.4 ± 0.4 | 501.5 ± 0.08 | 501.5 ± 0.5 | 501.5 ± 0.2 | 313.4 ± 0.3 | 501.5 ± 0.06 |
MFC | 313.4 ± 0.3 | 313.4 ± 0.3 | 626.9 ± 0.4 | 1003.0 ± 1 | 1003.0 ± 0.6 | 1003.0 ± 0.3 | 626.9 ± 0.3 | 1003.0 ± 1 | |
9 | MIC | 250.7 ± 0.5 | 141.0 ± 0.04 | 282.1 ± 0.4 | 250.8 ± 0.04 | 250.8 ± 0.08 | 250.8 ± 0.08 | 501.5 ± 0.3 | 250.8 ± 0.04 |
MFC | 501.5 ± 0.3 | 282.1 ± 0.05 | 564.2 ± 0.1 | 501.6 ± 0.03 | 501.6 ± 0.3 | 501.6 ± 0.3 | 1003.1 ± 0.2 | 501.6 ± 0.08 | |
10 | MIC | 119.2 ± 0.2 | 59.6 ± 0.02 | 119.2 ± 0.6 | 119.2 ± 0.05 | 59.6 ± 0.02 | 59.6 ± 0.03 | 59.6 ± 0.05 | 59.6 ± 0.02 |
MFC | 238.4 ± 0.2 | 119.2 ± 0.05 | 238.4 ± 0.5 | 238.4 ± 0.08 | 119.2 ± 0.03 | 119.2 ± 0.01 | 119.2 ± 0.03 | 119.2 ± 0.06 | |
11 | MIC | 432.4 ± 0.4 | 108.1 ± 0.06 | 216.2 ± 0.4 | 378.4 ± 0.04 | 189.2 ± 0.05 | 189.2 ± 0.06 | 432.4 ± 0.5 | 378.4 ± 0.06 |
MFC | 864.8 ± 0.5 | 216.2 ± 0.05 | 432.4 ± 0.4 | 756.7 ± 0.06 | 378.4 ± 0.3 | 378.4 ± 0.08 | 864.8 ± 0.5 | 756.7 ± 0.08 | |
12 | MIC | 135.1 ± 0.3 | 135.1 ± 0.06 | 270.2 ± 0.3 | 135.1 ± 0.06 | 135.1 ± 0.06 | 270.2 ± 0.06 | 135.1 ± 0.3 | 270.2 ± 0.05 |
MFC | 270.2 ± 0.2 | 270.2 ± 0.2 | 540.4 ± 0.2 | 270.2 ± 0.03 | 270.2 ± 0.3 | 540.4 ± 0.3 | 270.2 ± 0.2 | 540.4 ± 0.03 | |
13 | MIC | 81.0 ± 0.2 | 81.0 ± 0.06 | 162.0 ± 0.3 | 162.0 ± 0.06 | 81.0 ± 0.04 | 81.0 ± 0.04 | 81.0 ± 0.05 | 81.0 ± 0.01 |
MFC | 162.0 ± 0.2 | 162.0 ± 0.04 | 324.0 ± 0.5 | 324.0 ± 0.08 | 162.0 ± 0.04 | 162.0 ± 0.04 | 162.0 ± 0.3 | 162.0 ± 0.05 | |
14 | MIC | 78.9 ± 0.4 | 78.9 ± 0.03 | 157.9 ± 0.2 | 157.9 ± 0.04 | 78.9 ± 0.02 | 78.9 ± 0.05 | 78.9 ± 0.3 | 157.9 ± 0.03 |
MFC | 157.9 ± 0.3 | 157.9 ± 0.2 | 315.8 ± 0.1 | 315.8 ± 0.04 | 157.9 ± 0.08 | 157.9 ± 0.01 | 157.9 ± 0.4 | 315.8 ± 0.06 | |
15 | MIC | 342.2 ± 0.2 | 171.1 ± 0.4 | 342.2 ± 0.5 | 342.2 ± 0.08 | 342.2 ± 0.02 | 342.2 ± 0.03 | 342.2 ± 0.03 | 342.2 ± 0.04 |
MFC | 684.4 ± 0.3 | 342.2 ± 0.5 | 684.4 ± 0.1 | 684.4 ± 0.03 | 684.4 ± 0.06 | 684.4 ± 0.02 | 684.4 ± 0.5 | 684.4 ± 0.05 | |
Bifonazole | MIC | 480.0 ± 0.3 | 640.0 ± 0.1 | 480.0 ± 0.1 | 480.0 ± 0.10 | 480.0 ± 0.2 | 640 ± 0.2 | 480 ± 0.3 | 480 ± 0.06 |
MFC | 640.0 ± 0.5 | 800 ± 0.3 | 800.0 ± 0.4 | 640.0 ± 0.08 | 640.0 ± 0.2 | 800 ± 0.2 | 640 ± 0.4 | 640 ± 0.03 | |
Ketoconazole | MIC | 2850 ± 0.3 | 4750.0 ± 0.3 | 380.0 ± 0.2 | 380.0 ± 0.06 | 380.0 ± 0.3 | 380 ± 0.3 | 3800 ± 0.3 | 380 ± 0.06 |
MFC | 3800 ± 0,06 | 5700.0 ± 0.2 | 950.0 ± 0.5 | 950.0 ± 0.10 | 950.0 ± 0.3 | 950 ± 0.4 | 3800 ± 0.5 | 950 ± 0.08 |
No. | TPSA (A2) | Μ.Β. | nOHNH | nON | Violations | cLogP |
---|---|---|---|---|---|---|
1 | 58.12 | 301.4 | 1 | 4 | 0 | 3.67 |
2 | 78.35 | 317.39 | 2 | 5 | 0 | 3.28 |
3 | 78.35 | 317.39 | 2 | 5 | 0 | 3.28 |
4 | 67.35 | 331.42 | 1 | 5 | 0 | 3.54 |
5 | 76.59 | 261.45 | 1 | 6 | 0 | 3.42 |
6 | 103.94 | 346.39 | 1 | 7 | 0 | 3.88 |
7 | 103.94 | 346.39 | 1 | 7 | 0 | 3.88 |
8 | 58.12 | 319.39 | 1 | 4 | 0 | 3.83 |
9 | 58.12 | 319.39 | 1 | 4 | 0 | 3.83 |
10 | 58.12 | 335.84 | 1 | 4 | 0 | 4.23 |
11 | 58.12 | 270.29 | 1 | 4 | 0 | 4.78 |
12 | 58.12 | 370.29 | 1 | 4 | 0 | 4.78 |
13 | 58.12 | 370.29 | 1 | 4 | 0 | 4.78 |
14 | 58.12 | 380.29 | 1 | 4 | 0 | 4.50 |
15 | 58.12 | 380.29 | 1 | 4 | 0 | 4.50 |
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Haroun, M.; Tratrat, C.; Kolokotroni, A.; Petrou, A.; Geronikaki, A.; Ivanov, M.; Kostic, M.; Sokovic, M.; Carazo, A.; Mladěnka, P.; et al. 5-Benzyliden-2-(5-methylthiazol-2-ylimino)thiazolidin-4-ones as Antimicrobial Agents. Design, Synthesis, Biological Evaluation and Molecular Docking Studies. Antibiotics 2021, 10, 309. https://doi.org/10.3390/antibiotics10030309
Haroun M, Tratrat C, Kolokotroni A, Petrou A, Geronikaki A, Ivanov M, Kostic M, Sokovic M, Carazo A, Mladěnka P, et al. 5-Benzyliden-2-(5-methylthiazol-2-ylimino)thiazolidin-4-ones as Antimicrobial Agents. Design, Synthesis, Biological Evaluation and Molecular Docking Studies. Antibiotics. 2021; 10(3):309. https://doi.org/10.3390/antibiotics10030309
Chicago/Turabian StyleHaroun, Michelyne, Christophe Tratrat, Aggeliki Kolokotroni, Anthi Petrou, Athina Geronikaki, Marija Ivanov, Marina Kostic, Marina Sokovic, Alejandro Carazo, Přemysl Mladěnka, and et al. 2021. "5-Benzyliden-2-(5-methylthiazol-2-ylimino)thiazolidin-4-ones as Antimicrobial Agents. Design, Synthesis, Biological Evaluation and Molecular Docking Studies" Antibiotics 10, no. 3: 309. https://doi.org/10.3390/antibiotics10030309
APA StyleHaroun, M., Tratrat, C., Kolokotroni, A., Petrou, A., Geronikaki, A., Ivanov, M., Kostic, M., Sokovic, M., Carazo, A., Mladěnka, P., Sreeharsha, N., Venugopala, K. N., Nair, A. B., & Elsewedy, H. S. (2021). 5-Benzyliden-2-(5-methylthiazol-2-ylimino)thiazolidin-4-ones as Antimicrobial Agents. Design, Synthesis, Biological Evaluation and Molecular Docking Studies. Antibiotics, 10(3), 309. https://doi.org/10.3390/antibiotics10030309