Solvent effects on the structure-property relationship of anticonvulsant hydantoin derivatives: A solvatochromic analysis

Table 1 Physicochemical properties and pharmacokinetic data of the studied compounds

No.	R₁	R₂	log P^a	*%Abs.* ^b	log BB^b	f_B^b(%)	log k_A^c	ΣE_s^d	Σσ*^e
1	C₆H₅	CH₃	2.03	95.2	0.13	87.126	4.050	-2.55	0.60
2	C₆H₅	C₂H₅	2.56	95.7	0.07	91.983	4.280	-2.62	0.50
3	C₆H₅	n-C₃H₇	3.09	95.9	0	95.173	4.515	-2.91	0.48
4	C₆H₅	i-C₃H₇	2.91	96.0	0.04	90.15	4.182	-3.02	0.41
5	C₆H₅	CH₂ = CHCH₂	2.55	95.8	0.05	92.255	4.296	-2.94	0.70
6	C₆H₅	n-C₄H₉	3.62	96.1	-0.07	97.067	4.740	-2.94	0.47
7	C₆H₅	i-C₄H₉	3.44	96.1	-0.03	96.16	4.619	-3.48	0.47
8	C₆H₅	t-C₄H₉	2.94	96.2	0.05	96.275	4.632	-4.09	0.30
9	C₆H₅	cyc-C₅H₉	3.52	96.1	-0.04	92.757	4.327	-3.06	0.40
10	C₆H₅	cyc-C₆H₁₁	4.09	96.2	-0.13	94.537	4.458	-3.34	0.45
11	C₆H₅	C₆H₅CH₂	3.89	96.4	-0.14	95.395	4.536	-2.93	0.82
12	C₂H₅	CH₃	1.40	93.4	-0.20	46.132	3.153	-0.07	-0.10
13	C₂H₅	C₂H₅	1.93	94.1	-0.21	56.89	3.340	-0.14	-0.20
14	C₂H₅	n-C₃H₇	2.46	94.9	-0.17	70.307	3.594	-0.43	-0.22
15	C₂H₅	i-C₃H₇	2.28	94.8	-0.18	59.576	3.388	-0.54	-0.29
16	C₂H₅	CH₂ = CHCH₂	2.10	94.6	-0.19	65.146	3.492	-0.46	0.00
17	C₂H₅	n-C₄H₉	2.99	95.2	-0.12	81.654	3.868	-0.46	-0.23
18	C₂H₅	i-C₄H₉	2.81	95.2	-0.14	75.939	3.719	-1.00	-0.23
19	C₂H₅	C₆H₅CH₂	3.25	95.6	-0.01	95.044	4.503	-0.45	0.12
20	CH₃	CH₃	0.87	92.2	-0.20	95.044	4.503	0.00	0.00
21	CH₃	C₂H₅	1.40	93.3	-0.21	33.701	2.926	-0.07	-0.10
22	CH₃	n-C₃H₇	1.93	94.3	-0.2	45.258	3.137	-0.36	-0.12
23	CH₃	i-C₃H₇	1.75	94.3	-0.19	57.868	3.358	-0.47	-0.19
24	CH₃	n-C₄H₉	2.46	94.9	-0.16	70.494	3.598	-0.39	-0.13
25	CH₃	i-C₄H₉	2.28	94.8	-0.16	65.26	3.494	-0.93	-0.13

^acalculated by ACD Solaris v. 4.67.
^bhuman intestinal absorption data (%Abs.), the blood-brain permeation (log BB) and percentage plasma protein binding (f_b) were calculated by ChemSilico.
^cprotein binding affinities were obtained using Eq. 6.
^dsum of the values of the Taft steric parameters of R₁and R₂.
^esum of the values of the Taft electronic parameters of R₁and R₂.

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