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. Author manuscript; available in PMC: 2017 Feb 15.
Published in final edited form as: Eur J Med Chem. 2015 Dec 23;109:216–237. doi: 10.1016/j.ejmech.2015.12.036

Table 1.

SAR exploration on the nature of R group: cycloalkanes, small-branched alkanes and phenyls.

graphic file with name nihms-751453-f0009.jpg
Compound R FAAHa,b IC50(μM)±SD COX-1a,b IC50 (μM)±SD COX-2a,b IC50 (μM)±SD
2, URB597 - 0.0017±0.001 >100 >100
3a, flurbiprofen - >100 0.15±0.018 1.06±0.53
10a c-hexyl 8.2±2.4 7.9±2.1 >100
10b c-pentyl 4.8±3.2 4.4±2.0 > 100
10c c-butyl 48.7±9.0 0.72±0.02 >100
10d c-propyl >100 5.4±2.9 74.3±6.1
10e c-hexyl-CH2 0.36±0.06 0.60±0.04 >100
10f c-hexyl-(CH2)2 0.018±0.007 0.15±0.03 10.8±2.2
10g iso-propyl >100 3.9±2.1 >100
10h iso-butyl 4.1±2.1 8.2±2.1 >100
10i Ph 41.2±3.4 0.27±0.07 2.7±0.3
10j Ph-CH2 4.18±2.8 1.3±0.6 >100
10k Ph-(CH2)2 0.17±0.07 6.3±2.2 >100
10l Ph-(CH2)3 0.09±0.01 0.58±0.09 6.2±0.3
10m Ph-(CH2)4 0.027±0.010 3.7±2.8 >100
a

Values are reported as mean values of ≥3 experiments performed

b

IC50 values were not determined for compounds showing less than 50% inhibition at concentrations of 100 μM for FAAH and COXs.