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. Author manuscript; available in PMC: 2012 Dec 8.
Published in final edited form as: J Med Chem. 2011 Nov 8;54(23):8188–8194. doi: 10.1021/jm201148s

Table 2.

SAR studies of piclamilast analogs.

graphic file with name nihms-334892-f0004.jpg
Entry Cmpd R1 R2 R3 R4 R5 TbrPDEB1 IC50 (μM)a TbrPDEB2 IC50 (μM)a T. brucei EC50 (μM)
1 1 H graphic file with name nihms-334892-t0005.jpg OMe H H 4.7 ± 1.0 11.4± 1.1 9.6 ± 0.9
2 10 22 H OMe OMe H H >100 >100
3 11 H OEt OMe H H 16.5±3.4 34.0±0.9
4 12 H OPr OMe H H 13.6± 4.4 9.4±2.4 13.0±2.4
5 13 H OiPr OMe H H >30b >30b 27.6±7.1
6 14 22 H OBu OMe H H 7.7 ± 3.9 14.3±3.7 17.7±3.1
7 15 H OBn OMe H H 12.5±5.3 11.2±1.1 10.1±1.2
8 16 H OEt OEt H H >100 nd
9 17 H OMe OAc H H >100 nd
10 9 H OMe OMe OMe H >>100 nd >>100
11 18 Cl OMe OMe H H >>100 nd
12 19 H OMe OMe H Cl >>100 nd
a

IC50 values reported to be “>> x μM” if <25% inh at x μM; “> x μM” if 25-50% inh at x μM.

b

Measurement of a precise IC50 value was precluded by low compound solubility.