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. Author manuscript; available in PMC: 2008 Feb 1.
Published in final edited form as: Bioorg Med Chem Lett. 2006 Oct 28;17(3):745–749. doi: 10.1016/j.bmcl.2006.10.076

Table 1.

Binding and functional data for D2 compounds.

graphic file with name nihms-16893-0003.jpg
Compd. m n o X-Y R1 R2 D2a D3a D4a D3/D2 D4/D2 D2 functionb D3 functionb
Ki [nM] ± SEM EC50 [nM] ± SEM
5 1 1 0 CH-NH OH 2′-Cl 382 ±33 1860 ± 340 2820 ± 64 5 7 586 ± 210 ND
6 1 1 0 CH-NH OH 2′,3′-Cl 26.1 ± 2.0 273 ± 42 1550 ± 190 10 59 34.3 ± 6.8 232 ±7.7
7 1 1 0 CH-NH OH 3′-Cl 129 ± 22 450 ± 80 3540 ± 660 3 27 83.4 ± 10 ND
8 1 1 0 CH-NH OH 3′,4′-Cl 6.9 ± 1.0 111 ± 17 1100 ± 210 16 159 15.3 ± 0.8 41.5 ± 9.1
9 1 1 0 CH-NH OH 3′-CF3 106 ± 15 570 ± 44 3750 ± 140 5 35 69.1 ± 23 ND
10 1 1 0 CH-NH OH 4′-F 127 ± 7.2 490 ± 74 6090 ± 580 4 48 ND ND
11 1 1 0 CH-NH OH 4′-OH 5360 ± 1100 16800 ± 6500 1360 ± 270 3 0.3 ND ND
12 1 1 0 CH-NH OH 4′-OMe 177 ± 61 2130 ± 300 679 ± 60 12 4 ND ND
13 1 1 0 CH-NH OH 4′-OHex 159 ± 60 1950 ± 350 1490 ± 150 12 9 216 ± 1.7 ND
14 1 1 0 CH-NH OH 4′-Ph 98.4 ± 19 467 ± 38 129 ± 26 5 1 ND ND
15 2 1 0 CH-NH OH 4′-Cl 201 ± 21 2100 ± 490 3870 ± 770 10 19 260 ± 91 ND
16 1 1 1 CH-NH OH 4′-Cl 2890 ± 560 5480 ± 2900 3930 ± 1200 2 1 ND ND
17 2 0 0 CH-NH OH 4′-Cl 4265 ± 2280 4270 ± 400 2440 ± 1400 1 1 ND ND
18 1 1 0 CH-NH Me 4′-Cl 992 ± 192 2100 ± 150 2750 ± 140 2 3 314 ± 4.2 347±7.4
19 1 1 0 CH-NH NH2 4′-Cl 184 ± 40 382 ± 55 2293 ± 545 2 12 ND ND
20 1 1 0 CH-NH NHAc 4′-Cl 83.1 ± 47 193 ± 80 348 ± 39 2 4 24.8 ± 7.6 ND
21 1 1 0 CH-NH F 4′-Cl 120 ± 34 211 ± 67 365 ± 63 2 3 ND ND
22 1 1 0 CH-NH CN 4′-Cl 199 ± 24 684 ± 180 2270 ± 350 3 11 225 ± 80 ND
23 1 1 0 CH-NH COOMe 4′-Cl 60.0 ± 9.5 544 ± 128 3930 ± 2500 9 66 76.7 ± 21 ND
24 1 1 0 CH-NH COOEt 4′-Cl 58.8 ± 20 724 ± 120 3520 ± 1320 12 60 ND ND
25 1 1 0 CH-NH CH2NH2 4′-Cl >10000 >5000 >20000 ND ND
26 1 1 0 CH-NH CH2NHAc 4′-Cl 2000 ± 640 12500 ±1300 4450 ± 750 6 2 ND ND
27 1 1 0 CH-NH CH2OH 4′-Cl 2370 ± 560 106 ±19 1940 ± 250 0.04 1 ND ND
28 1 1 0 CH-NH OMe 4′-Cl 68.1 ± 22 262 ± 73 34.1 ± 6.0 4 1 34.7 ± 2.9 248 ± 84
29 1 1 0 CH-NH OAllyl 4′-Cl 165 ± 91 718 ± 35 1190 ± 360 4 7 ND ND
30 1 1 0 CMe-NH OH 4′-Cl 15.4 ± 14 44.1 ± 11 2990 ± 180 3 194 2.13 ± 0.3 20.2 ± 4.2
31 1 1 0 N-NH OH 3′,4′-Cl 438 ± 46 156 ± 22 677 ± 148 0.4 2 ND ND
32 1 1 0 N-NH OH 4′-Cl 548 ± 80 440 ± 88 2146 ± 616 1 4 ND ND
33 1 1 0 CH-O OH 3′,4′-Cl 21.0 ± 4 28.0 ± 6 167 ± 35 1 8 ND ND
34 1 1 0 CH-O OH 4′-Cl 21.0 ± 4 53.0 ± 12.5 404 ± 24 3 19 ND ND
35 1 1 0 CH-O OH 4′-SMe 54.0 ±13 139 ± 7.9 153 ± 35 3 3 ND ND
36 1 1 0 CH-NMe OH 4′-Cl 29.6 ± 6.2 238 ± 100 5140 ± 3330 8 174 20.0 ± 4.5 98.6 ± 29
37 1 1 0 CH-NHex OH 4′-Cl 188 ± 27 488 ± 280 8890 ± 5600 3 47 166.0 ± 35 661 ± 56
38 1 1 0 n/ac OH 4′-Cl >10000 ND >20000 ND ND
2a11 1 1 0 CH-NH OH 4′-SMe 23.9 ± 5.5 638 ± 159 319 ± 58 27 13 ND ND
2b11 1 1 0 CH-NHd OH 4′-SMe 5.5 ± 0.1 580 ± 92 567 ± 140 105 103 ND ND
1, L741,62610 1 1 0 CH-NH OH 4′-Cl 11.2 ± 0.8 163 ± 32 1520 ± 280 15 136 4.46 ± 0.9 90.4 ± 15
a

Inhibtion of binding assay in HEK 293 cells transfected with either hD2L, hD3, or hD4 dopamine receptors, radioligand 125I-IABN.15, 16

b

Functional assays using inhibition of quinpirole stimulation in hD2 and hD3 receptors transfected into CHO cells. These data were obtained through the service of CTDP, Division of Treatment Research and Development, NIDA, using a contract (N01DA-1-8816) protocol. ND = not determined.

c

1-((1H-indol-2-yl)methyl)-4-(4′-chlorophenyl)piperidin-4-ol.

d

1-((5-Methoxy-1H-indol-3-yl)methyl)-4-(4′-(methylthio)phenyl)piperidin-4-ol