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. Author manuscript; available in PMC: 2014 Jun 27.
Published in final edited form as: J Med Chem. 2013 Jun 17;56(12):5115–5129. doi: 10.1021/jm400511s

Table 2.

Inhibition of GSK-3β by Maleimides 21–31.

graphic file with name nihms495215u2.jpg
Cmpd. R1 R2 R3 R4 IC50 (nM)a
21 H Me Me - 11.2±3.1
22 H Me t-Bu - 148±15
23 H -(CH2)2OMe Me - 114±16
24 H - - - 4.2±0.7
25 F - - - 3.7±0.5
26 Br - - - 11.5±2.2
27 H - - 2-pyrazinyl 0.20±0.06
28 H - - 4-pyridylmethyl 0.59±0.11
29 F - - 1-piperidinyl 1.9±0.4
30 F - - 4-piperidinopiperidin1-yl 0.53±0.01
31 F - - 4-morpholinyl 0.013±0.005
a

The synthesized maleimides were evaluated for their ability to inhibit phosphorylation of primed substrate (YRRAAVPPSPSLSRHSSPHQ(pS)EDEEE; 20 μM) by human GSK-3β in the presence of 10 μM ATP concentration. These compounds were tested at Reaction Biology Inc.37 and IC50 values are presented as either average of duplicates ± SEM.