. Author manuscript; available in PMC: 2013 Aug 9.

Published in final edited form as: J Med Chem. 2012 Jul 23;55(15):6751–6761. doi: 10.1021/jm3001218

Table 1.

IC₅₀ values of hydroxylated R-antofine analogs

Cmpd	E-ring oxygenation	IC₅₀ (μM)				Predicted C.brain/C. blood
Cmpd	E-ring oxygenation	A549	DU145	KB	KBvin	Predicted C.brain/C. blood
3a	13R-OH	2.81 ± 0.42	3.20 ± 0.49	1.83 ± 0.36	3.42 ± 0.38	0.059
3b	13S-OH	0.27 ± 0.035	0.85 ± 0.094	0.50 ± 0.077	0.64 ± 0.080	0.059
7	C13-OMe, Δ12–13	5.97 ± 0.84	10.30 ± 2.02	12.00 ± 2.18	2.64 ± 0.35	0.044
8	C12, C=O	0.29 ± 0.051	0.71 ± 0.083	0.50 ± 0.064	0.43 ± 0.052	0.334
9a	12R-OH	0.61 ± 0.087	0.70 ± 0.078	0.78 ± 0.085	0.64 ± 0.081	0.062
9b	12S-OH	2.27 ± 0.40	1.80 ± 0.39	1.81 ± 0.23	2.21 ± 0.32	0.062
R-anto-fine	--	0.022 ± 0.007	0.025 ± 0.005	0.036 ± 0.008	0.025 ± 0.007	0.980