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. Author manuscript; available in PMC: 2010 Apr 9.
Published in final edited form as: J Med Chem. 2009 Apr 9;52(7):1864–1872. doi: 10.1021/jm801343r

Table 1.

Activity of triazolopyrimidine-based derivatives against DHODH and P. falciparum

graphic file with name nihms103786t1.jpg
Compd Name Ar IC50(µM)b
PfDHODH		 IC50(µM)b
PbDHODH		 IC50(µM)b
hDHODH		 EC50(µM)c
Pf 3D7 cells
2 a DSM1 2-Naphthyl 0.047 ± 0.02 0.23 ± 0.04 >200 0.076 ± 0.04b
3 a DSM2 2-Anthracenyl 0.056 ± 0.02 3.7 ± 0.14 >200 0.19 ± 0.12b
4a DSM12 Ph >200 >10 >200 >100
8 DSM106 2-F-Ph >100 >100 ND >50
9 DSM95 2-Cl-Ph >100 >100 ND 30 ± 0.01
10 DSM93 2-CH3-Ph >100 >100 ND >50
11 DSM91 2-CF3-Ph >100 >100 ND ND
12 DSM92 2-CN-Ph >100 >100 ND 25 ± 0.002
13 DSM72 3-F-Ph 9.2 ± 0.2 >100 ND 34 ± 0.03
14 DSM75 3-Cl-Ph 1.4 ± 0.13 31 ± 3.2 >100 8.5 ± 0.002
15 DSM94 3-CH3-Ph 4.9 ± 0.52 >100 ND 37 ± 0.02
16 DSM73 3-CF3-Ph 14 ± 0.0 55 ± 10 ND 19 ± 0.01
17 DSM131 4-F-Ph 19 ± 2.0 >100 ND 50 ± 1.1
18 DSM89 4-Cl-Ph 1.6 ± 0.24 5.7 ± 0.9 >100 12 ± 0.002
19 DSM98 4-Br-Ph 0.78 ± 0.25 1.3 ± 0.3 >100 4.2 ± 0.07
20 DSM97 4-CH3-Ph 4.2 ± 0.35 16 ± 2.5 ND 6.4 ± 0.004
21 DSM74 4-CF3-Ph 0.28 ± 0.02 0.38 ± 0.02 >100 0.34 ± 0.04b
22 DSM100 4-OCH3-Ph 4.6 ± 0.14 >50 ND 14 ± 0.005
23 DSM87 4-OCF3-Ph 1.2 ± 0.21 4 ± 0.7 >100 3.8 ± 0.01
24 DSM88 4-OCHF2-Ph 2.8 ± 0.28 25 ± 2.4 ND 8.2 ± 0.01
25 DSM99 4-NO2-Ph 4.3 ± 0.14 3.7 ± 0.7 ND ND
26 DSM69 4-C6H5-Ph 5.3 ± 0.8 ND ND >50
27 DSM84 4-C6H5CH2-Ph 2.2 ± 0.32 >100 ND 5.0 ± 0.0
28 DSM110 2,3-Di-F-Ph 39 ± 7.5 >100 ND ND
29 DSM107 2,5-Di-F-Ph >50 >100 ND >50
30 DSM108 2,6-Di-F-Ph >100 >100 ND >50
31 DSM109 2,3,4-Tri-F-Ph 29 ± 4.4 >100 ND >50
32 DSM111 2,4,5-Tri-F-Ph 17 ± 3.6 >100 ND >50
33 DSM120 2,4,6-Tri-F-Ph >100 >100 ND ND
34 DSM132 2,3,5,6-Tetra-F-Ph >100 >100 ND >50
35 DSM133 2,3,4,5,6-Penta-F-Ph >100 >100 ND >50
36 DSM85 2-F-4-CH3-Ph 27 ± 2.8 >100 ND 35 ± 0.002
37 DSM112 3,4-Di-F-Ph 8.0 ± 1.1 10 ± 5.6 ND >50
38 DSM121 3,5-Di-F-Ph 9.4 ± 1.2 21 ± 3.5 ND ND
39 DSM126 3,5-Di-CF3-Ph >100 >100 ND >5
40 DSM82 3-CH3-4-F-Ph 4.6 ± 0 21 ± 1.4 ND 8.7 ± 0.001
41 DSM124 3-CF3-4-Cl-Ph 0.8 ± 0.28 2.4 ± 0.2 >100 >5
42 DSM128 3-CF3-4-Br-Ph 0.45 ± 0.07 1.5 ± 0.4 >100 2.6 ± 0.002
43 DSM122 3-CF3-4-CH3-Ph 1.55 ± 0.49 7.3 ± 1.2 >100 8.1 ± 0.1
44 DSM123 3,4-Di-CH3-Ph 0.35 ± 0.21 4.0 ± 0.4 >100 4.8 ± 2.3b
45 DSM81 3-CF3-4-CN-Ph 4.9 ± 0.7 11 ± 1.2 ND 8.8 ± 0.001
46 DSM83 3-F-4-CH3-Ph 0.86 ± 0.09 3.2 ± 0.4 >100 3.6 ± 0.004
47 DSM125 3-F-4-CF3-Ph 0.077 ± 0.03 0.26 ± 0.05 >100 1.3 ± 0.1b
a

Compounds reported previously22. ND, not determined.

b

standard error of the mean.

c

standard error of the fit.