. Author manuscript; available in PMC: 2010 Mar 12.

Published in final edited form as: J Med Chem. 2009 Mar 12;52(5):1358–1369. doi: 10.1021/jm8012344

Table 1.

^a. Affinites (K_i) of the Benzoylbenzovesamicol Analogs, 9a-e, (+)-9e, (-)-9e, for VAChT and Sigma Receptors (σ₁, σ₂) Assayed in vitro

Ligands	VAChT^b (K_i [nM])	σ₁^c (K_i [nM])	σ₂^d (K_i[nM])	VAChT: σ ratio		Log P^e
Ligands	VAChT^b (K_i [nM])	σ₁^c (K_i [nM])	σ₂^d (K_i[nM])	VAChT/σ₁	VAChT/σ₂	Log P^e
Vesamicol^f	2.0 ± 1.0	25.8 ± 8.0	34.5 ± 2.0	25.8	34.5	1.40
Benzovesamicol^g	0.055 ± 0.01	ND	ND	ND	ND	2.44
(+)-FBT^h	0.22±0.05	21.6±3.9	35.9±6.3	98	163	1.99
9a	4.30 ± 1.00	219.6 ± 17.3	320.0 ± 6.6	51	74	2.78
9b	0.25 ± 0.02	297.7 ± 18.7	592.6 ± 95.2	1188	2368	3.73
9c	1.68+0.14	ND	ND	ND	ND	1.56
9d	0.48+0.03	ND	ND	ND	ND	2.16
(±)9e	2.70 ± 0.40	191.1 ± 57.7	251.3 ± 39.2	71	93	2.99
(+)-9e	108 ± 15	185.97 ± 38.89	277.93 ± 26.66	1.7	2.8	2.99
(-)-9e	4.1 ± 0.6	658.60 ± 118.40	319.23 ± 36.64	160	78	2.99

K_i values (mean ± SEM) were determined in at least three experiments;

K_i VAChT is measured using Torpedo synaptic vesicles;

σ₁binding is measured using guinea pig brain membranes;

σ₂ binding is measured using rat liver preparations.

Calculated value at pH = 7.4 by ACD/I-Lab ver. 7.0 (Advanced Chemistry Development, Inc., Canada).