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. Author manuscript; available in PMC: 2014 Nov 1.
Published in final edited form as: Bioorg Med Chem Lett. 2013 Sep 10;23(21):10.1016/j.bmcl.2013.09.001. doi: 10.1016/j.bmcl.2013.09.001

Table 4.

Second Generation Amide SAR – Thiazoles

graphic file with name nihms524282u4.jpg
cpd X R mGlu5 pIC50 (± SEM)a mGlu5 IC50 (nM) % Glu Max (± SEM)a,b
32 F H 5.75 ± 0.25 1790 3.2 ± 1.2
33 F 4-(C3H5) 6.62 ± 0.08 238 1.7 ± 0.3
34 F 4-CH3, 5-F 7.27 ± 0.03 54 1.5 ± 0.1
35 F 4-CH2F 6.66 ± 0.03 217 1.6 ± 0.4
36 F 4-CHF2 5.66 ± 0.06 2200 1.7 ± 0.4
37 F 4-CF3 5.49 ± 0.05 3230 1.5 ± 0.5
38 Cl 4-(C3H5) 7.09 ± 0.19 82 1.7 ± 0.2
39 Cl 4-CH3, 5-F 7.44 ± 0.09 37 1.4 ± 0.2
40 Cl 4-CH2F 7.01 ± 0.08 99 1.3 ± 0.2
41 Cl 4-CHF2 6.51 ± 0.07 310 1.2 ± 0.2
42 Cl 4-CF3 6.68 ± 0.04 210 1.2 ± 0.4
a

Calcium mobilization mGlu5 assay; values are average of n ≥ 3

b

Amplitude of response in the presence of 30 μM test compound as a percentage of maximal response (100 μM glutamate); average of n ≥ 3