Table 1.

Percent inhibition and IC₅₀ of manzamine-derived compounds 152–166.

Compound	R1	R2	R3	R4	X-Y	GSK3β Inhibition at 25 µM	GSK3β IC50
152	OTs	H	H		HC=CH	80.4	n.d. a
153	OMe	H	Me		HC=CH	72.4	n.d. a
154	OEt	H	Et		HC=CH	78.0	10.4
155	O-i-But	H	i-But		HC=CH	24.2	n.d. a
156	H	H	(CH2)11CH3		HC=CH	0	n.d. a
157	H	H	t-BuOCOMe		HC=CH	3	n.d. a
158	H	H	H		HC=CH	88.4	n.d. a
159	OH	H	H		(CH2)2	29.0	n.d. a
160	OH	H	H		HC=CH	30.0	n.d. a
161	H	H	H		(CH2)2	0	n.d. a
162		H	H		HC=CH	78.8	8.5
163		H	H		HC=CH	76.7	7.2
164		H	H		HC=CH	63.0	23.0
165	H	H	H		HC=CH	71.2	5.4
166	OCOMe	H	H		HC=CH	79.1	4.8

^a n.d. = not determined.