Table 2.
Structure of ring-substituted (2E)-N-aryl-3-phenylprop-2-enamides 1–16, IC50 (μM) values related to PET inhibition in spinach chloroplasts in comparison with 3-(3,4-dichlorophenyl)-1,1-dimethylurea (DCMU) standard, in vitro anti-Staphylococcus activities MIC (μM) in comparison with standard ampicillin (AMP), in vitro antitubercular activity MIC (μM (µg/mL)) in comparison with standard isoniazid (INH), in vitro antifungal activity MIC (μM (µg/mL)) of compounds 1–16 compared to standard benomyl (BNM), and in vitro antiproliferative (Tox) assay (IC50 (μM)) of chosen compounds compared to standard camptothecin (CMP).
| Comp. | R | MIC (μM (µg/mL)) | Tox IC50 (μM) | PET IC50 (μM) | ||||||
|---|---|---|---|---|---|---|---|---|---|---|
| SA | MRSA 63718 | MRSA SA 630 | MRSA SA 3202 | Mtb | FA | BS | ||||
| 1 | H | >1146 (>256) |
>1146 (>256) |
>1146 (>256) |
>1146 (>256) |
286 (64) |
1146 (256) |
143 (32) |
– | 250 |
| 2 | 3-CH3 | >1078 (>256) |
>1078 (>256) |
>1078 (>256) |
>1078 (>256) |
67.43 (16) |
270 (64) |
33.71 (8) |
>30 | 343 |
| 3 | 4-CH3 | >1078 (>256) |
>1078 (>256) |
>1078 (>256) |
>1078 (>256) |
134 (32) |
1078 (256) |
539 (128) |
– | 320 |
| 4 | 2-F | >1061 (>256) |
>1061 (>256) |
>1061 (>256) |
>1061 (>256) |
265 (64) |
1061 (256) |
66.32 (16) |
– | 223 |
| 5 | 3-F | >1061 (>256) |
>1061 (>256) |
>1061 (>256) |
>1061 (>256) |
66.31 (16) |
531 (128) |
16.58 (4) |
>30 | 165 |
| 6 | 3-CF3 | 27.47 (8) |
27.47 (8) |
27.47 (8) |
27.47 (8) |
27.47 (8) |
54.93 (16) |
54.93 (16) |
22.72 ± 1.73 | 189 |
| 7 | 2,5-CH3 | >1018 (>256) |
>1018 (>256) |
>1018 (>256) |
>1018 (>256) |
254 (64) |
1019 (256) |
1019 (256) |
– | 338 |
| 8 | 2,5-Cl | >876 (>256) |
>876 (>256) |
>876 (>256) |
>876 (>256) |
876 (256) |
876 (256) |
876 (256) |
– | 67.1 |
| 9 | 2,6-Cl | >876 (>256) |
>876 (>256) |
>876 (>256) |
>876 (>256) |
876 (256) |
876 (256) |
876 (256) |
– | 1380 |
| 10 | 3,4-Cl | 438 (128) |
876 (256) |
438 (128) |
876 (256) |
27.38 (8) |
219 (64) |
110 (32) |
29.81 ± 0.31 | 54.9 |
| 11 | 3,5-Cl | 438 (128) |
876 (256) |
109 (64) |
438 (128) |
27.38 (8) |
219 (64) |
110 (32) |
29.44 ± 1.73 | 5.1 |
| 12 | 2,6-Br | >671 (256) |
>671 (256) |
>671 (256) |
>671 (256) |
167 (64) |
671 (256) |
671 (256) |
– | 732 |
| 13 | 3,5-CF3 | 22.27 (8) |
22.27 (8) |
22.27 (8) |
22.27 (8) |
22.27 (8)) |
713 (256) |
356 (128) |
22.59 ± 1.88 | 111 |
| 14 | 2-F-5-Br | >799 (>256) |
>799 (>256) |
>799 (>256) |
>799 (>256) |
199 (64) |
799 (256) |
49.98 (16) |
– | 188 |
| 15 | 2-Br-5-F | >799 (>256) |
>799 (>256) |
>799 (>256) |
>799 (>256) |
199 (64) |
799 (256) |
799 (256) |
– | 205 |
| 16 | 2-Cl-5-CF3 | >785 (>256) |
>785 (>256) |
>785 (>256) |
>785 (>256) |
785 (256) |
785 (256) |
785 (256) |
– | 63.2 |
| AMP | – | 5.72 (2) |
45.81 (16) |
45.81 (16) |
45.81 (16) |
– | – | – | – | – |
| INH | – | – | – | – | – | 36.55 (5) |
– | – | – | – |
| BNM | – | – | – | – | – | – | 1.94 (0.5) |
17.22 (5) |
– | – |
| CMP | – | – | – | – | – | – | – | – | 0.16 ± 0.07 | – |
| DCMU | – | – | – | – | – | – | – | – | – | 2.1 |
SA = Staphylococcus aureus ATCC 29213; MRSA = clinical isolates of methicillin-resistant S. aureus 63718, SA 630, and SA 3202 (National Institute of Public Health, Prague, Czech Republic); Mtb = Mycobacterium tuberculosis H37Ra; FA = Fusarium avenaceum (Fr.) Sacc. IMI 319947; BS = Bipolaris sorokiniana (Sacc.) Shoemaker H-299 (NCBI GenBank accession No. MH697869).