Table 2.

Inhibitory activity of 2-(adamantan-1-ylamino)thiazol-4(5H)-one derivatives. The comparison of the experimental data and the binding energies collected in the docking study. The calculation results were averaged over 8 protein structures (11β-HSD1) available in the PDB database; the corresponding standard deviations are given.

No.	R1	R2	% of 11β-HSD1 Inhibition 10 μM	IC50 11β-HSD1 [µM]	Binding Energy [kcal/mol]	% of 11β-HSD2 Inhibition 10 μM
3a	H	H	22.27 ± 5.31	nd	−7.91 ± 0.20	29.81 ± 4.21
3b	H	CH3	62.15 ± 3.59	3.52 ± 0.19	−8.48 ± 0.23 c	44.71 ± 4.19
3c	H	C2H5	69.22 ± 5.12	5.44 ± 0.32	−8.58 ± 0.24 c	14.42 ± 1.16
3d	H	C3H7	72.37 ± 2.63	3.23 ± 0.26	−8.63 ± 0.27 c	28.85 ± 4.11
3e	H	CH(CH3)2	76.40 ± 2.55	1.19 ± 0.21	−8.96 ± 0.31 c	16.35 ± 2.06
3f	CH3	CH3	65.99 ± 1.12	6.11 ± 0.62	−8.46 ± 0.11	24.52 ± 3.24
3g	H	C6H5	46.32 ± 5.53	nd	−9.99 ± 0.45 c	18.27 ± 3.18
3h	H	C6H5p-Br	15.30 ± 0.49	nd	−10.14 ± 0.46 c	41.83 ± 6.12
3i	-(CH2)5-		82.82 ± 2.05	0.31 ± 0.05	−10.04 ± 0.33	44.71 ± 3.37
3j	-(CH2)3-		74.13 ± 2.85	3.32 ± 0.24	−8.98 ± 0.16	41.35 ± 4.22
control	-		84.78 ± 6.23 a	0.16 ± 0.15 a	-	46.15 ± 3.16 b/ 55.77 ± 4.28 a

^a for carbenoxolone, ^b for 11β-glycyrrhetinic acid, ^c value additionally averaged over two stereoisomers of the given ligand.