Table 1.
| No. | Materials Tested | Antimicrobial Assay | Test Microorganism (MIC, µg/mL) | Antibiotic | Antimicrobial Effect | |||
|---|---|---|---|---|---|---|---|---|
| S. aureus ATCC 29213 | E. faecalis ATCC 29212 |
E. coli
ATCC 25922 |
S. enterica ATCC 1307 | |||||
| 1 | (E)-N-(2-((4-cinnamoylphenyl)amino)-2-oxoethyl)-N,N-dimethyloctan-1-aminium chloride | BMD | 1 | 2 | 3 | 4 | VAN, MEM | Strong |
| 2 | (E)-N-(2-((4-(3-(3-chlorophenyl)acryloyl)phenyl)amino)-2-oxoethyl)-N,N dimethyloctan-1-aminium chloride | BMD | 2 | 2 | 4 | 8 | VAN, MEM | Strong |
| 3 | (E)-N-(2-((4-(3-(3-chlorophenyl)acryloyl)phenyl)amino)-2-oxoethyl)-N,N-dimethyloctan-1-aminium chloride | BMD | 2 | 1 | 4 | 4 | VAN, MEM | Strong |
| 4 | (E)-N-(2-((4-(3-(4-fluorophenyl)acryloyl)phenyl)amino)-2-oxoethyl)-N,N-dimethyloctan-1-aminium chloride | BMD | 2 | 2 | 2 | 4 | VAN, MEM | Strong |
| 5 | (E)-N-(2-((4-(3-(3-fluorophenyl)acryloyl)phenyl)amino)-2-oxoethyl)-N,N-dimethyloctan-1-aminium chloride | BMD | 32 | 64 | >128 | >128 | VAN, MEM | Not good |
| 6 | (E)-N-(2-((4-(3-(2-fluorophenyl)acryloyl)phenyl)amino)-2-oxoethyl)-N,N-dimethylbutan-1-aminium chloride | BMD | 16 | 16 | 64 | 128 | VAN, MEM | Good except S. enterica |
| 7 | (E)-N-(2-((4-(3-(2-fluorophenyl)acryloyl)phenyl)amino)-2-oxoethyl)-N,N-dimethyloctan-1-aminium chloride | BMD | 0.5 | 1 | 2 | 4 | VAN, MEM | Strong |
| 8 | (E)-N-(2-((4-(3-(2-fluorophenyl)acryloyl)phenyl)amino)-2-oxoethyl)-N,N-dimethyldodecan-1-aminium chloride | BMD | 4 | 8 | 16 | 32 | VAN, MEM | Good |
| 9 | (E)-N-(2-((4-(3-(2-fluorophenyl)acryloyl)phenyl)amino)-2-oxoethyl)-N,N-dimethyltetradecan-1-aminium chloride | BMD | 8 | >128 | >128 | >128 | VAN, MEM | Effective against S. aureus only |
| 10 | (E)-N-(2-((4-(3-(2-fluorophenyl)acryloyl)phenyl)amino)-2-oxoethyl)-N,N-dimethyloctadecan-1-aminium chloride | BMD | >128 | >128 | >128 | >128 | VAN, MEM | No activity |
| 11 | (E)-N-(2-((4-(3-(2,3-difluorophenyl)acryloyl)phenyl)amino)-2-oxoethyl)-N,N-dimethyloctan-1-aminium chloride | BMD | 0.5 | 2 | 2 | 8 | VAN, MEM | Strong |
| 12 | (E)-N-(2-((4-(3-(2,4-difluorophenyl)acryloyl)phenyl)amino)-2-oxoethyl)-N,N-dimethyloctan-1-aminium chloride | BMD | 2 | 2 | 4 | 4 | VAN, MEM | Strong |
| 13 | (E)-N-(2-((4-(3-(2,6-difluorophenyl)acryloyl)phenyl)amino)-2-oxoethyl)-N,N-dimethyloctan-1-aminium chloride | BMD | 32 | 32 | 128 | 128 | VAN, MEM | Fair |
| 14 | (E)-N-(2-((4-(3-(2-ethoxy-5-nitrophenyl)acryloyl)phenyl)amino)-2-oxoethyl)-N,N-dimethyloctan-1-aminium chloride | BMD | 8 | 2 | >128 | >128 | VAN, MEM | Strong against S. aureus and E. faecalis |
| 15 | (E)-N-(2-((4-(3-(4-(tert-butyl)phenyl)acryloyl)phenyl)amino)-2-oxoethyl)-N, N-dimethyloctan-1-aminium chloride | BMD | 2 | 4 | 8 | 16 | VAN, MEM | Strong |
| 16 | (E)-N,N-dimethyl-N-(2-oxo-2((4(3(2(trifluoromethyl)phenyl)acryloyl)phenyl)amino)ethyl)octan-1-aminium chloride | BMD | 2 | 4 | 16 | 16 | VAN, MEM | Strong |
| 17 | (E)-N,N-dimethyl-N-(2-oxo-2-((4-(3-(p-tolyl)acryloyl)phenyl)amino)ethyl)octan-1-aminium chloride | BMD | 1 | 1 | 4 | 8 | VAN, MEM | Strong |
| 18 | (E)-N-(2-((4-(3-(4-methoxyphenyl)acryloyl)phenyl)amino)-2-oxoethyl)-N,N-dimethyloctan-1-aminium chloride | BMD | 1 | 2 | 4 | 4 | VAN, MEM | Strong |
| 19 | (E)-N,N-dimethyl-N-(2-((4-(3-(naphthalen-2-yl)acryloyl)phenyl)amino)-2-oxoctan-1-aminium chloride | BMD | 2 | 2 | 8 | 8 | VAN, MEM | Strong |
| 20 | (E)-N,N-dimethyl-N-(2-oxo-2-((4-(3-(pyridin4yl)acryloyl)phenyl)amino)ethyl)butan-1-aminium chloride | BMD | 128 | 128 | >128 | >128 | VAN, MEM | Not good |
| 21 | (E)-N,N-dimethyl-N-(2-oxo-2-((4-(3-(pyridin-4yl)acryloyl)phenyl)amino)ethyl)octan-1-aminium chloride | BMD | 4 | 8 | 16 | 32 | VAN, MEM | Good |
| 22 | (E)-N,N-dimethyl-N-(2-oxo-2-((4-(3-(pyridin-3-yl)acryloyl)phenyl)amino)ethyl)octan-1-aminium chloride | BMD | 4 | 8 | 16 | 32 | VAN, MEM | Good |
| 23 | (E)-N,N-dimethyl-N-(2-oxo-2-((4-(3-(pyridinedin-2yl)acryloyl)phenyl)amino)ethyl)octan-1-aminium chloride | BMD | 4 | 8 | 16 | 32 | VAN, MEM | Good |
| 24 | (E)-N-(2-((4-(3-(6-bromopyridin-2-yl)acryloyl)phenyl)amino)-2-oxoethyl)-N, N-dimethyloctan-1-aminium chloride | BMD | 4 | 8 | 16 | 32 | VAN, MEM | Good |
| 25 | (E)-((2-((4-(3-(3-fluoropyridin-2-yl)acryloyl)phenyl)amino)-2-oxoethyl)(methyl)(octyl)-l4-azanyl)methylium chloride | BMD | 2 | 8 | 8 | 16 | VAN, MEM | Strong |
| 26 | (E)-N-(2-((4-(3-(furan-2-yl)acryloyl)phenyl)amino)-2-oxoethyl)-N,N-dimethyloctan-1-aminium chloride | BMD | 1 | 4 | 4 | 16 | VAN, MEM | Strong |
| 27 | (E)-N,N-dimethyl-N-(2-oxo-2-((4-(3-(thiophen-2-yl)acryloyl)phenyl)amino)ethyl)butan-1-aminium chloride | BMD | 0.5 | 1 | 4 | 8 | VAN, MEM | Strong |
| 28 | (E)-N, N-dimethyl-N-(2-oxo-2-((4-(3-(thiophen-2-yl)acryloyl)phenyl)amino)ethyl)octan-1-aminium chloride | BMD | 32 | 32 | 64 | 128 | VAN, MEM | Fair |
| 29 | (E)-N,N-dimethyl-N-(2-oxo-2-((3-(3-(thiophen2-yl)acryloyl)phenyl)amino)ethyl) octan-1-aminium chloride | BMD | 2 | 4 | 16 | 16 | VAN, MEM | Strong |
| S. aureus ATCC 25923 | B. cereus ATCC 11778 |
E. coli
ATCC 25922 |
P. aeruginosa ATCC 27853 | |||||
| 30 | 2,2′,4,4′,5,5′-hexamethoxychalcone | BMD | >2000 | >2000 | >2000 | 2000 | TET | Not active |
| 31 | 2′-hydroxy-4,4’,5′-trimethoxychalcone | BMD | 2000 | 1000 | 2000 | 1000 | TET | Not active |
| 32 | 3,4-methylenedloxy-2′-3′,4′,6′-tetramethoxychalcone | BMD | >2000 | 2000 | 2000 | 2000 | TET | Not active |
| 33 | 4,4′-dimethoxychalcone | BMD | >2000 | >2000 | >2000 | 2000 | TET | Not active |
| 34 | 3’,4′-dimethoxychalcone | BMD | 1000 | 1000 | 2000 | 1000 | TET | Not active |
| 35 | 2-hydroxy’-3’,4′-dimethoxychalcone | BMD | 1000 | 1000 | 1000 | 1000 | TET | Not active |
| 36 | 2′-acetoxy-3′-4′,4’,6′-tetramethoxychalcone | BMD | 2000 | 2000 | 1000 | 1000 | TET | Not active |
| 37 | 2,3′,4,4′,5-pentamethoxychalcone | BMD | 2000 | 2000 | 1000 | 2000 | TET | Not active |
| 38 | 2,2′,4′,5-tetramethoxychalcone | BMD | 1000 | 250 | 2000 | 2000 | TET | Active against B. cereus |
| 39 | 2,3,3′,4,4′,6-hexamethoxychalcone | BMD | 2000 | 2000 | 2000 | 2000 | TET | Not active |
| 40 | Cordoin | BMD | 2000 | 2000 | 2000 | 2000 | TET | Not active |
| 41 | 4-hydroxycordoin | BMD | 2000 | 1000 | 2000 | 2000 | TET | Not active |
| 42 | Isocordoin | BMD | 2000 | 2000 | 2000 | 2000 | TET | Not active |
| 43 | 4-hydroxyisocordoin | BMD | 31.2 | 31.2 | 1000 | 1000 | TET | Strong for S. aureus and B. cereus |
| 44 | Derricin | BMD | 2000 | 2000 | 2000 | 2000 | TET | Not active |
| 45 | 2-hydroxyderricin | BMD | 2000 | 2000 | 2000 | 2000 | TET | Not active |
| 46 | 3-hydroxyderricin | BMD | 2000 | 1000 | 2000 | 2000 | TET | Not active |
| 47 | 4-hydroxyderricin | BMD | 7.8 | 3.9 | 2000 | 2000 | TET | Strong |
| 48 | 4-methoxyderricin | BMD | 2000 | 2000 | 2000 | 2000 | TET | Not active |
| 49 | 2′,4,4′-trihydroxychalcone | BMD | 62.5 | 62.5 | 2000 | 2000 | TET | Strong |
| 50 | 2’, 4,4’-trihydroxy-3-preny’-3’geranylchalcone | BMD | 31.2 | 15.6 | 1000 | 1000 | TET | Strong |
| 51 | 2’, 4,4’-trihydroxy’-3’geranylchalcone | BMD | 31.2 | 15.6 | 1000 | 1000 | TET | Strong for S. aureus and B. cereus |
| 52 | 4-hydroxyisolonchocarpin | BMD | 1000 | 1000 | 2000 | 2000 | TET | Not active |
| 53 | Lonchocarpin | BMD | 2000 | 2000 | 1000 | 2000 | TET | Not active |
| 54 | 4-hydroxylonchocarpin | BMD | 2000 | 2000 | 2000 | 2000 | TET | Not active |
| 55 | 4-hydroxyisolonchocarpin | BMD | 2000 | 1000 | 2000 | 2000 | TET | Not active |
| 56 | Isolonchocarpin | BMD | 2000 | 2000 | 1000 | 1000 | TET | Not active |
| 57 | 4-hydroxy-4′-methoxychalcone | BMD | 500 | 500 | 2000 | 1000 | TET | Not active |
| 58 | 2-hydroxydihydrochalcone | BMD | 2000 | 2000 | 2000 | 2000 | TET | Not active |
| 59 | 2’,4,5′-trihydroxy-3,4-methylene-dioxy-dihydrochalcone | BMD | 2000 | 2000 | 2000 | 2000 | TET | Not active |
| 60 | 2’,4,5′-trihydroxy-dihydrochalcone | BMD | 250 | 250 | >2000 | 2000 | TET | Active against S. aureus and B. cereus |
| S. aureus | B. subtilis | S. typhimurium | P. aeruginosa | |||||
| 61 | 1,3-Bis(4-chlorophenyl)-3-(phenylsulfonyl)propan-1-one | BMD | 250 | 15.62 | 125 | 125 | AMP, KMN | Strong |
| 62 | 1-Phenyl-3-(4-chlorophenyl)-3-(phenylsulfonyl)propane-1-one | BMD | 125 | 62.5 | 125 | 62.5 | AMP, KMN | Strong |
| 63 | 1-(4-Chlorophenyl)-3-(3-nitrophenyl)-3-phenylsulfonylprop-ane-1-one | BMD | 125 | 62.5 | 62.5 | 62.5 | AMP, KMN | Strong |
| 64 | 1-(4-Bromophenyl)-3-phenyl-3-(phenylsulfonyl) propane-1-one | BMD | 125 | 62.5 | 250 | 62.5 | AMP, KMN | Strong |
| 65 | 1-(4-Bromophenyl)-3-(3,4-dimethoxyphenyl)-3-(phenylsulfonyl)propane-1-one | BMD | 62.5 | 62.5 | 1.95 | 62.5 | AMP, KMN | Strong |
| 66 | 1-(4-Bromophenyl)-3-(3,4,5-trimethoxyphenyl)-3-(phenylsulfonyl) propane-1-one | BMD | 125 | 31.25 | 1.95 | 125 | AMP, KMN | Strong |
| 67 | 1-Phenyl-3-phenyl- 3-phenylsulfonylpropane-1-one | BMD | 62.5 | 31.25 | 1.95 | 125 | AMP, KMN | Strong |
| 68 | 1,5-Di(4-methylphenyl)-1,5-bis(phenylsulfonyl)pentan-3-one | BMD | 62.5 | 62.5 | 31.25 | 62.5 | AMP, KMN | Strong |
| 69 | 1,5-Di(4-chlorophenyl)-1,5-bis(phenylsulfonyl)pentan-3-one | BMD | 250 | 31.25 | 15.62 | 250 | AMP, KMN | Strong |
| 70 | 1,5-Di(phenyl)-1,5-bis(phenylsulfonyl)pentan-3-one | BMD | 62.5 | 125 | 250 | 62.5 | AMP, KMN | Strong |
| 71 | 1,5-Di(4-methoxyphenyl)-1,5-bis(phenylsulfonyl)pentan-3-one | BMD | 250 | 31.25 | 62.5 | 125 | AMP, KMN | Strong |
MIC: Minimum inhibitory concentration; BMD: Broth microdilution; VAN: Vancomycin (MIC: 2 µg/mL for S. aureus); MEM: Meropenem (MIC: <0.125 µg/mL for E. coli); TET: Tetracycline (MIC: 1 µg/mL for S. aureus, 0.25 µg/mL for B. cereus, 2 µg/mL cereus, 32 µg/mL for P. aeruginosa); AMP: Ampicillin (MIC: 500 µg/mL for S. aureus, 7.81 µg/mL for B. subtilis, 15.62 µg/mL for S. typhimurium, 250 µg/mL for P. aeruginosa); KMN: Kanamycin (MIC: 500 µg/mL for S. aureus, 250 µg/mL for B. subtilis, 125 µg/mL for S. typhimurium, 125 µg/mL for P. aeruginosa).