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. Author manuscript; available in PMC: 2013 Nov 12.
Published in final edited form as: Angew Chem Int Ed Engl. 2012 Oct 12;51(46):11463–11467. doi: 10.1002/anie.201206231

Table 4.

VHL Ligands with Optimized C- and N-terminal Fragments

graphic file with name nihms422813u4.jpg
# R1 R2[b] IC50 (μM) [a] (10% DMSO) IC50 (μM)[a] (1% DMSO) Ki [b] (μM)
16 Cl graphic file with name nihms422813t25.jpg 37.8 ± 3.1 20.5 ± 1.9[c] 15.2
1 5-oxazole 7.0 ± 0.5 4.1 ± 0.4[c] 3.0
6 5-(4-methyl) thiazole 3.8 ± 0.3 3.2 ± 0.4 2.4
39 Cl graphic file with name nihms422813t26.jpg 62.9 ± 2.0 N.D. N.D.
40 5-oxazole 27.0 ± 0.7 19.5 ± 1.0 14.5
41 5-(4-methyl) thiazole 14.1 ± 0.3 11.2 ± 0.9 8.3
32 Cl graphic file with name nihms422813t27.jpg 19.6 ± 0.8 N.D. N.D.
42 5-oxazole 39.5 ± 3.7 31.5 ± 1.9 23.3
43 5-(4-methyl) thiazole 7.7 ± 0.4 26.8 ± 1.8 19.9
36 Cl graphic file with name nihms422813t28.jpg 17.0 ± 0.6 N.D. N.D.
44 5-oxazole 21.2 ± 0.4 24.1 ± 0.6 17.8
45 5-(4-methyl) thiazole 4.9 ± 0.2 11.9 ± 0.7 8.8
33 Cl graphic file with name nihms422813t29.jpg 8.0 ± 0.1 N.D. N.D.
46 5-oxazole 40.3 ± 3.9 47.3 ± 1.3 35.1
47 5-(4-methyl) thiazole 12.0 ± 0.5 11.0 ± 0.8 8.1
35 Cl graphic file with name nihms422813t30.jpg 17.0 ± 0.6 N.D. N.D.
48 5-oxazole 23.4 ± 0.4 18.0 ± 0.4 13.3
49 5-(4-methyl) thiazole 3.5 ± 0.2 3.71 ± 0.03 2.8
28 Cl graphic file with name nihms422813t31.jpg 10.4 ± 0.8 N.D. N.D.
50 5-oxazole 18.9 ± 2.3 14.0 ± 0.7 10.4
51 5-(4-methyl) thiazole 1.76 ± 0.06 0.90 ± 0.03 0.67
[a]

IC50 values determined by the displacement of FAM-DEALA-Hyp-YIPD from complex of VCB, with SEM reported.

[b]

Kis calculated from IC50s (1% DMSO) as described by Huang.[22]

[c]

Literature value.[18]