Table 1.

The molecular structure and affinities to SERT (IC₅₀, nM) and 5-HT_1A receptor affinities (K_i, nM) of the studied compounds. In the brackets the inhibition constant of [³H]5-HT at human tissue is included.

Compound	R1	R2	R3	n	R4	SERT IC50 ± SEM, nM	5-HT1A Ki ± SEM, nM
1	NO2	H	H	-	H	ND (Ki=0.17nM)	ND
2	H	H	H	-	H	ND (Ki=30 nM)	230
3	NO2	CH3	H	4	b	267.8 ± 26.3	711.0 ± 21.0
4	NO2	H	H	4	b	921.1 ± 8.2	10600 ± 3500
5	NO2	CH3	H	4	c	1350 ± 211	776.5 ± 117.5
6	NO2	H	H	4	c	25900 ± 1100	1100 ± 400
7	NO2	CH3	H	4	d	806.8 ± 85.2	221.0 ± 34.6
8	NO2	H	H	4	d	616.3 ± 1.1	2100 ± 400
9	NO2	H	H	4	a	4130 ± 900	59000 ± 23100
10	H	H	Cl	4	d	2800 ± 200	1400 ± 100
11	C(O)NHCH3	H	H	4	c	18800 ± 700	3200 ± 800
12	H	CH3	H	4	a	33.4 ± 17.0 (8)*	13[17]
13	H	H	H	4	a	95.5 ± 37.2	39[17]
14	H	CH3	H	3	a	(80)*	275[19]
15	H	CH3	H	4	b	(50)*	37 ± 6[18]
16	H	CH3	H	4	c	75.0 ± 16.3	24 ± 3[18]
17	H	H	H	4	c	111.6 ±27.2	39 ± 7[16]
18	H	CH3	H	4	d	170.7 ±68.5	15 ± 3[18]
19	H	H	H	4	d	146.4 ±19.4	11 ± 2[16]

^*data obtained from Servier laboratories