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. Author manuscript; available in PMC: 2012 Jan 21.
Published in final edited form as: ChemMedChem. 2009 Oct;4(10):1615–1629. doi: 10.1002/cmdc.200900226

Table 1.

Potency (EC50) and maximal stimulation (Emax)s of hCB1 and hCB2 by compounds 13–32.[a]

graphic file with name nihms346512u1.jpg
Compd R1 R2 R2 position γ-[35S]GTP hCB1 γ-[35S]GTP hCB2
EC50 [nm ± SEM] Emax [%][b] EC50 [nm ± SEM] Emax [%][b]
13 phenyl N-(2-iodophenyl) 5 >10 000 ND[c] >10 000 ND
14 phenyl N-cyclohexyl 5 >10 000 ND 406 ± 1.4 47.1
15 phenyl 1-piperidyl 5 >10 000 ND >10 000 ND
16 phenyl N-(2-iodophenyl) 6 >10 000 ND >10 000 ND
17 phenyl N-cyclohexyl 6 >10 000 ND 478 ± 1.3 54.3
18 phenyl 1-piperidyl 6 >10 000 ND 128 ± 32 88.3
33 S enantiomer (1) of 18 6 >10 000 ND 108.02 86
34 R enantiomer (2) of 18 6 >10 000 ND 960.89 43.3
19 graphic file with name nihms346512t1.jpg 1-piperidyl 6 856 ± 1.2 60 48.9± 1.4 97.1
20 graphic file with name nihms346512t2.jpg N-cyclohexyl 6 >10 000 ND 839 ± 5.5 105
21 phenyl graphic file with name nihms346512t3.jpg 6 >10 000 ND 246 ± 1.3 48.7
22 phenyl morpholine 6 >10 000 ND 5583 ± 4.4 93
23 phenyl graphic file with name nihms346512t4.jpg 6 2580 ± 1.5 ND 95.3±1.8 91
24 phenyl graphic file with name nihms346512t5.jpg 6 >10 000 ND 659 ±1.4 49
27 1-naphthyl N-cyclohexyl 6 >10 000 ND >10 000 ND
28 1-naphthyl 1-piperidyl 6 >10 000 ND >10 000 ND
29 2-naphthyl 1-piperidyl 6 >10 000 ND 875 ± 1.4 112
30 4-chlorohenyl 1-piperidyl 6 1363 ± 1.4 86.9 56.2± 1.2 102
31 4-methoxyphenyl 1-piperidyl 6 >10 000 ND 234.68 77.1
32 4-pyridine 1-piperidyl 6 >10 000 ND 2801.44 62.5
[a]

CB1 and CB2 assay data are presented as the mean of two determinations; reproducibility was monitored by the use of compound 7 as reference. For replicate determinations, the maximum variability tolerated in the test was ±20 % around the average of the replicates.

[b]

Efficacies for CB1 or CB2 are expressed as percentage relative to the efficacy of compound 7.

[c]

ND =not determined (plateau was not reached at a dose of 10 μm).