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. Author manuscript; available in PMC: 2013 Jul 31.
Published in final edited form as: Bioorg Med Chem. 2011 Nov 22;20(1):215–224. doi: 10.1016/j.bmc.2011.11.008

Table 1.

rTRPV1 activities of N-(4-tert-butylbenzyl)-2-[4-(methylsulfonylamino)phenyl] propionamide ligands

graphic file with name nihms491934t1.jpg
R3 R2 R5 Ki (nM)
Binding Affinityc 		EC50 (nM)
Agonismc 		Ki (nM)
Antagonismc
1 63.0 NE 54
2 53.5 NE 9.2
3 51.0 (17%)a (84%)b
4 470 (±130) NE 118 (±35)
53 H H H 106 (±34) NE 17.5 (±1.6)
54 F H H 46.2 (±3.0) NE 7.6 (±1.6)
55 Cl H H 30.7 (±7.4) NE 29.5 (±8.5)
56 Br H H 7.4 (±1.5) NE 25.0 (±7.4)
57 I H H 23.3 (±7.1) NE 30.0 (±2.2)
58 F H F 19.9 (±6.1) NE 7.4 (±2.1)
59 H F H 360 (±110) NE 120 (±27)
60 H Cl H 1420 (±280) NE 4500 (±1000)
61 CN H H 344 (±99) NE 467 (±60)
62 CO2tBu H H 6700 (±1200) NE (16%)b
63 CO2H H H NE NE NE
64 CO2CH3 H H 1606 (±53) NE 952 (±120)
65 CONHBn H H 3710 (±470) NE (23%)b
66 graphic file with name nihms491934t2.jpg H H WE NE (37%)b
67 graphic file with name nihms491934t3.jpg H H WE NE (34%)b
68 graphic file with name nihms491934t4.jpg H H 7000 (±1600) NE (13%)b
69 graphic file with name nihms491934t5.jpg H H NE NE NE
70 CH3 H H 32.8 (±6.1) NE 18.9 (±8.3)
71 OCH3 H H 540 (±130) NE 232 (±71)
a

only fractional calcium uptake compared with that induced by 300 nM capsaicin

b

only fractional antagonism

c

Values represent mean ± SEM from 3 or more experiments

NE, no effect. WE, weak effect (quantitation of fractional agonism/antagonism is from 1 – 3 experiments).