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. Author manuscript; available in PMC: 2022 Apr 1.
Published in final edited form as: Bioorg Chem. 2021 Feb 9;109:104702. doi: 10.1016/j.bioorg.2021.104702

Table 1.

The Radioligand Binding Affinity to the KOR, MOR, and DOR and Selectivity Profiles of Compounds 1a-e and 6a-e.a

graphic file with name nihms-1676179-t0010.jpg
Compounds R1 R2 Ki (nM) Selectivity
KOR MOR DOR μ/κ δ/κ
1a OH Cl 0.15 ± 0.04b 0.10 ± 0.04b 602.20 ± 22.30b 0.67 4015
6a H Cl 10.46 ± 1.38 18.84 ± 3.01 2123.66 ± 101.18 1.8 203
1b OH Br 0.18 ± 0.03b 0.63 ± 0.18b 173.70 ± 134.90b 3.5 965
6b H Br 7.44 ± 0.7 24.51 ± 3.23 2086.15 ± 71.59 3.3 280
1c (NCP) OH CN 0.13 ± 0.01b 1.25 ± 0.55b 75.30 ± 7.00b 9.6 579
6c H CN 6.13 ± 0.74 58.27 ± 5.16 3375.73 ± 743.96 9.5 551
1d OH CH3 0.58 ± 0.12b 0.39 ± 0.20b 90.10 ± 17.10b 0.67 155
6d H CH3 96.07 ± 14.84 39.03 ± 2.56 3649.72 ± 158.17 0.41 38.0
1e OH OCH3 0.46 ± 0.04b 0.60 ± 0.23b 160.40 ± 6.60b 1.3 349
6e H OCH3 86.91 ± 9.22 45.63 ± 4.59 5900.42 ± 300.78 0.53 67.9
a

The values are the mean ± SEM of at least three independent experiments.

b

Data have been reported in Reference [15], and are presented here for comparison purposes.