Table 1. Structures and LSD1 inhibitory activities of compounds 1–35.

	R1	R2	LSD1 IC50 (μM)
1	4-OBn	(4-methylpiperazin-1-yl)-carbonylmethyl	0.0098
2	4-(6-F-pyridin-3-yl)	same as above	0.077
3	4-Br	same as above	0.035
4	4-(6-Cl-pyridin-3-yl)	same as above	0.15
5	2-Br	same as above	>100
6	3-Br	same as above	>100
7	4-OBn	-H	0.91
8	6-F-pyridin-3-yl	-H	5.3
9	4-Br	-H	25
10	4-Br	(piperazin-1-yl)-carbonylmethyl	0.064
11	4-Br	(piperidin-1-yl)-carbonylmethyl	0.62
12	4-Br	(pyrrolidin-1-yl)-carbonylmethyl	3.6
13	4-H	same as 10	0.19
14	4-H	same as 11	1.3
15	4-Br	(piperidin-4-yl)-methyl	0.26
16	4-H	same as above	0.062
17	4-Br	-Bn	5.0
18	4-Br	-(4-OH)-Bn	94
19	4-Br	-(4-NH2)-Bn	>100
20	4-Br	-(4-NMe2)-Bn	71
21	4-Br	(pyridin-4-yl)-methyl	>100
22	4-Br	-COCH3	15.4
23	4-Br	-CONHPh	7.4
24	4-Br	= CH-Ph	15.6
25	4-Br	= CH-(4-Br-Ph)	1.2
26	4-Br	= CH-(2-OMe-Ph)	0.74
27	4-Br	= CH-(3-OMe-Ph)	0.90
28	4-Br	= CH-(2,3,4-OMe-Ph)	94
29	4-Br	= CH-(4-NMe2-Ph)	11
30	4-Br	= CH-(pyridine-4-yl)	14
31	4-H	-NH2	5.8
32	4-H	(piperazin-1-yl)-carbonylmethylamino	0.67
33	4-H	(piperazin-1-yl)-carboxamido	84
34	4-Br	(piperidin-4-yl)-methylamino	1.7
35	1-(4-methylpiperazin-1-yl)-2-((3-phenylprop-2-yn-1-yl)amino)ethan-1-one		36.4