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. 2019 Oct 29;20(21):5385. doi: 10.3390/ijms20215385

Table 1.

Structures of the carbamate derivatives 1–25, experimental log kw values and electronic Hammett’s σ parameters; in vitro PET, AChE and BChE inhibition (IC50 [μM]) compared with standards 3-(3,4-dichlorophenyl)-1,1-dimethylurea (DCMU) rivastigmine (RIV) and galanthamine (GLT) and in vitro viability (WST) assays (IC50 [μM]) of investigated compounds. ChE inhibition is expressed as the mean ± SD (n = 3 experiments).

graphic file with name ijms-20-05385-i001.jpg

No. R log kw σ a PET
IC50 [µM]		 AChE
IC50 [µM]		 BChE
IC50 [µM]		 SI b WST
IC50 [µM]
1. H 6.52 ± 0.13 0 4.90 53.52 ± 0.40 73.29 ± 0.28 0.73 >30
2. 2-OH 6.00 ± 0.04 −0.38 0.48 42.15 ± 2.06 8.37 ± 0.03 5.04 3.08 ± 0.07
3. 3-OH 5.59 ± 0.03 0.12 4.94 59.70 ± 0.43 19.08 ± 0.17 3.13 3.47 ± 0.08
4. 4-OH 5.40 ± 0.03 −0.37 483 36.22 ± 1.65 22.70 ± 0.24 1.60 6.43 ± 0.29
5. 2-OCH3 5.85 ± 0.21 −0.28 >500 38.63 ± 1.81 81.47 ± 0.21 0.47 –
6. 3-OCH3 6.26 ± 0.03 0.12 234 29.39 ± 0.44 130.30 ± 1.37 0.23 >30
7. 4-OCH3 6.09 ± 0.03 −0.27 >500 28.37 ± 0.74 152.54 ± 4.54 0.19 >30
8. 2-CH3 6.24 ± 0.02 −0.17 >500 46.41 ± 0.14 105.40 ± 2.78 0.44 –
9. 3-CH3 6.61 ± 0.03 −0.07 447 48.51 ± 3.77 131.22 ± 2.88 0.37 –
10. 4-CH3 6.62 ± 0.03 −0.17 452 45.04 ± 1.76 132.75 ± 2.46 0.34 –
11. 2-F 6.32 ± 0.02 0.06 51.5 43.03 ± 1.07 81.52 ± 4.81 0.53 >30
12. 3-F 6.44 ± 0.02 0.34 49.2 45.10 ± 1.43 160.29 ± 7.89 0.28 >30
13. 4-F 6.30 ± 0.02 0.06 22.9 62.65 ± 1.41 181.13 ± 10.05 0.35 >30
14. 2-Cl 6.74 ± 0.03 0.22 >500 47.15 ± 0.92 108.29 ± 1.74 0.44 –
15. 3-Cl 6.90 ± 0.02 0.37 332 48.12 ± 1.63 96.23 ± 5.29 0.50 –
16. 4-Cl 6.94 ± 0.03 0.23 >500 42.56 ± 0.23 115.98 ± 0.60 0.68 –
17. 2-Br 6.82 ± 0.03 0.22 354 46.27 ± 1.09 62.60 ± 5.59 0.74 –
18. 3-Br 7.05 ± 0.03 0.39 390 54.37 ± 0.83 107.33 ± 0.43 0.51 –
19. 4-Br 7.16 ± 0.04 0.23 42.3 53.18 ± 0.01 72.58 ± 3.72 0.73 >30
20. 2-CF3 6.90 ± 0.04 0.51 453 38.08 ± 0.16 104.17 ± 0.36 0.37 –
21. 3-CF3 7.32 ± 0.03 0.43 432 51.16 ± 1.03 88.87 ± 0.71 0.58 –
22. 4-CF3 7.53 ± 0.02 0.51 >500 42.79 ± 2.45 77.76 ± 0.97 0.55 –
23. 2-NO2 6.53 ± 0.06 0.77 43.2 46.14 ± 2.62 63.12 ± 1.14 0.73 >30
24. 3-NO2 6.40 ± 0.04 0.71 >500 49.42 ± 0.47 197.00 ± 11.28 0.25 –
25. 4-NO2 6.58 ± 0.04 0.78 253 26.35 ± 0.84 190.35 ± 6.61 0.14 >30
DCMU – – – 2.1 – – – –
RIV – – – – 50.10 ± 3.08 19.95 ± 0.31 1.46 –
GLT – – – – 4.0 ± 0.13 7.96 ± 0.59 0.56 –

a calculated using ACD/Percepta 14.0.0; b SI (index selectivity) = IC50 (AChE)/IC50 (BChE). A higher selectivity to BChE is indicated in bold.