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. Author manuscript; available in PMC: 2012 Oct 1.
Published in final edited form as: Eur J Med Chem. 2011 Aug 29;46(10):5154–5161. doi: 10.1016/j.ejmech.2011.08.031

Table 1.

Sigma receptor binding affinities and selectivity ratios of 1, 4a–4f, 9a–9i and haloperidola

graphic file with name nihms326637u1.jpg
Compd R1 R2 R3 σ-1 (Ki, nM) σ-2 (Ki, nM) σ-1/σ-2
1 - - - 4.17 ± 0.62 0.39 ± 0.06 10.7
4a H A-ring H 3.28±0.32 1.90±0.16 1.7
4b H B-ring H 71.50±1.53 13.32±0.61 5.4
4c H C-ring H 140.7±5.7 3.66±0.83 38.4
4d CH3CO A-ring H 5.33±2.12 2.31±0.02 2.3
4e CH3CO B-ring H 2.13±0.31 3.30±0.30 0.6
4f CH3CO C-ring H 14.55±1.42 1.42±0.10 10.2
9a H A-ring D-ring 92.43±1.90 12.30±2.34 7.5
9b H B-ring D-ring 222.33±22.41 9.96±1.19 22.3
9c H C-ring D-ring 713.5±163.5 46.29±7.18 15.4
9d H A-ring E-ring 90.87±12.30 22.55±1.10 4.0
9e H B-ring E-ring 1202±73.89 83.33±3.90 14.4
9f H C-ring E-ring 2948.4±374.4 7.45±0.71 395.8
9g H A-ring F-ring 34.50±4.84 10.07±2.01 3.4
9h H B-ring F-ring 279.0±40.5 157.0±1.6 1.8
9i H C-ring F-ring 613.66±38.29 12.02±1.15 51.1
haloperidol 3.35±0.80 80.60±14.10 0.042
a

Affinities (Ki in nM) were determined in rat brain homogenates. Sigma-1 receptors were labeled with [3H](+)-pentazocine. Sigma-2 receptors were labeled with [3H]DTG in the presence of (+)-pentazocine to block sigma-1 receptors. Nonspecific binding was determined in the presence of haloperidol. The values in this table represent the mean ± SEM from replicate assays.