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. Author manuscript; available in PMC: 2008 Sep 15.
Published in final edited form as: J Med Chem. 2007 Jul 18;50(16):3906–3920. doi: 10.1021/jm070311l

Table 3.

Inhibitory activities of compounds with free hydrogen on the nitrogen of 4- and 8-position substituents

graphic file with name nihms62594f8.jpg
Comp. Type R1 ENT1 inhibitory activity in K562 cells determined by flow cytometry
%Inhibition at 10μM IC50 (nM) Ki (nM)
DMSO - - 0.0 ± 0.7 ND a ND
NBMPR - - 97.1 ± 0.4 7.6 0.43
Lidoflazine - - 90.0 ± 0.2 4954 279.9
DP A graphic file with name nihms62594t16.jpg 86.7 ± 0.1 144.8 8.18
39 A NH2 6.5 ± 0.1 ND ND
40 A MeNH 4.1 ± 0.9 ND ND
41 B -1.0 ± 0.1 ND ND
42 A EtNH 24.0 ± 1.0 ND ND
43 B 0.7 ± 0.5 ND ND
44 A n-PropylNH 79.5 ± 1.0 5,310 300
45 B 5.7 ± 0.3 ND ND
46 A iso-PropylNH 81.7 ± 1.4 3,381 191
47 B 14.1 ± 1.2 ND ND
48 A n-ButylNH 87.3 ± 0.1 2,407 136
49 B 61.6 ± 0.1 8,655 489
50 A iso-ButylNH 92.0 ± 0.2 673 38
51 B 24.9 ± 0.1 ND ND
52 A tert-ButylNH 81.2 ± 0.1 297 16.8
53 B 28.0 ± 0.1 ND ND
54 A n-PentylNH 56.4 ± 0.4 2,476 139.9
55 B 12.5 ± 1.4 ND ND
56 A iso-PentylNH 86.8 ± 0.6 2,136 120.7
57 B 7.56 ± 0.1 ND ND
58 A tert-PentylNH 94.4 ± 0.2 260 14.7
59 B 16.1 ± 0.3 ND ND
60 A graphic file with name nihms62594t17.jpg 48.7± 0.9 7,554 427.6
61 B 6.2 ± 1.3 ND ND
62 A graphic file with name nihms62594t18.jpg 84.1 ± 0.3 1,838 104.1
63 B 23.0 ± 2.6 ND ND
64 A graphic file with name nihms62594t19.jpg 90.8 ± 0.2 279.7 15.8
65 B 4.9 ± 0.2 ND ND
66 A graphic file with name nihms62594t20.jpg 80.9 ± 0.1 940 53.1
67 B 1.4 ± 0.3 ND ND
68 A graphic file with name nihms62594t21.jpg 5.8 ± 0.5 ND ND
69 B 6.6 ± 3.9 ND N. D.
70 A graphic file with name nihms62594t22.jpg 11.9 ± 1.8 ND ND
71 B 3.8 ± 0.2 ND ND
a

ND = Not Determined.