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. Author manuscript; available in PMC: 2021 Mar 31.
Published in final edited form as: Bioorg Med Chem Lett. 2019 Dec 17;30(4):126899. doi: 10.1016/j.bmcl.2019.126899

Table 2.

SAR of analogs of exo-tert-butyl-3-amino-9-azabicyclo[3.3.1]nonane-9-carboxylate.

graphic file with name nihms-1680297-t0003.jpg
Entry R CXCR6: β-arrestin CXCR6: cAMP
IC50 (μM) % response IC50 (μM) % response
56 2-methoxyphenyl > 50 NA > 50 NA
57 3-methoxyphenyl > 50 NA > 50 NA
58 4-methoxyphenyl > 50 NA > 50 NA
59 2-chlorophenyl 6.8 99 11.5 101
60 3-chlorophenyl 9.5 97 14.8 100
61 4-chlorophenyl 23.7 90 38.6 58
62 2-napthyl 3.4 94 47.3 30
63 2-quinolinyl 6.7 88 40.3 88
64 2-indolyl 23.7 64 > 50 NA
65 3-indolyl > 50 NA > 50 NA
66 2-imidazo [1,2-a] pyridine > 50 NA > 50 NA
67 2-benzothiophenyl 0.9 93 25.0 49
68 2-benzothiazolyl 0.3 101 7.9 85
69 2-benzoxazolyl 6.9 83 > 50 26
70 2-benzimidazolyl 10.5 84 > 40 NA
71 2-benzothiazolylmethyl > 50 NA > 50 NA
72 benzothiazole-2-carbonyl 12.7 75 > 50 NA