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. Author manuscript; available in PMC: 2010 Jul 21.
Published in final edited form as: Bioorg Med Chem. 2007 Dec 4;16(5):2212–2225. doi: 10.1016/j.bmc.2007.11.078

Table 2.

ATX inhibitory evaluation of compounds 26–46

graphic file with name nihms213606u2.jpg
Compounds X R ATX activity (%)
1 μM 10 μM 100 μM
26 =O –H 79 95 76
27 –OHa –H 88 88 56
28 =O –CH3 60 67 72
29 –OHa –CH3 50 14 25
30 =O –CH(CH3)2 109 77 24
31 –OH (a)b –CH(CH3)2 115 57 13
32 –OH (b)b –CH(CH3)2 72 78 23
33 =O –CH2CH(CH3)2 89 48 25
34 –OH (a) –CH2CH(CH3)2 68 53 23
35 –OH (b) –CH2CH(CH3)2 93 64 52
36 –OH (a) –CH2Ph 88 70 70
37 –OH (b) –CH2Ph 92 99 67
38 =O –CH2CH2CH2–c 49 18 9
39 –OHa –CH2CH2CH2–c 83 43 16
40 =O graphic file with name nihms213606t1.jpg 91 70 28
41 –OH (a) graphic file with name nihms213606t2.jpg 88 51 25
42 –OH (b) graphic file with name nihms213606t3.jpg 93 75 26
43 –OHa graphic file with name nihms213606t4.jpg 80 35 28
44 –OHa graphic file with name nihms213606t5.jpg 64 28 13
45 –OH (a) graphic file with name nihms213606t6.jpg 83 41 19
46 –OH (b) graphic file with name nihms213606t7.jpg 78 46 61
a

Racemic products were tested.

b

a refers to the diastereomer that elutes first, b refers to the diastereomer that elutes second from normal phase silica gel based column chromatography.

c

The compounds were synthesized from protected L-proline.