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. 2023 Jun 16;28(12):4806. doi: 10.3390/molecules28124806

Table 2.

Chemical structures of synthesized oxime derivatives and JNK binding affinity of the compounds.

graphic file with name molecules-28-04806-i003.jpg
Compd. R1 R2 R3 R4 R5 R6 JNK1 JNK2 JNK3 Selectivity Index
Kd (µM) JNK1/JNK3 JNK2/JNK3
TRYP-Ox H H H H H H 0.15 ± 0.08 1.0 ± 0.14 0.28 ± 0.21 0.15 3.6
4a H NO2 H H H H N.B. N.B. 0.86 ± 0.042 >40 >40
4b H Br H H H H 3.2 ± 0.21 8.5 ± 3.2 0.41 ± 0.07 7.8 20.7
4c H Et H H H H 2.6 ± 0.4 1.3 ± 0.01 0.49 ± 0.09 5.3 2.7
4d H OMe H H H H N.B. N.B. 0.34 ± 0.03 >100 >100
4e H Ph H H H H N.B. N.B. 0.34 ± 0.04 >100 >100
4f H NO2 H H Br H N.B. N.B. N.B.
4g Me H H H H H 6.2 ± 1.8 14.0 ± 0.7 0.40 ± 0.04 15.5 35
4h H H Me H H H 0.67 ± 0.35 0.57 ± 0.12 0.23 ± 0.04 2.9 2.5
4i H H H H CF3 H N.B. N.B. 11.0 ± 1.4 >3 >3
4j H H H H Br H 4.1 ± 0.6 7.4 ± 0.6 1.9 ± 0.4 2.2 3.9
4k H H H H H Br N.B. N.B. 5.7 ± 1.8 >6 >6
4l H H H H H F 1.1 ± 0.1 0.72 ± 0.22 0.43 ± 0.04 2.6 1.7
4m H H H H H NO2 N.B. N.B. 6.1 ± 0.4 >5.6 >5.6
4n H H H H NO2 H N.B. N.B. 8.7 ± 1.0 >3.9 >3.9
4o H Me H H Me H 3.7 ± 0.5 6.9 ± 0.2 0.87 ± 0.16 4.3 7.9
4p Me H H Me H H N.B. N.B. N.B.
4q H OMe H H OMe H N.B. N.B. N.B.
4r H H OMe H H OMe 4.6 ± 0.6 5.8 ± 1.6 3.2 ± 1.1 1.4 1.8
4s H H Br H H Br N.B. N.B. N.B.
4t H Br H H Br H N.B. N.B. N.B.
4u Br H H Br H H N.B. N.B. N.B.
graphic file with name molecules-28-04806-i004.jpg
Compd. R JNK1 JNK2 JNK3 Selectivity Index
Kd (µM) JNK1/JNK3 JNK2/JNK3
5a -CH2COOEt N.B. N.B. N.B.
5b -CH(COOEt)2 16.5 ± 0.7 N.B. N.B.
5c -COOCH3 1.7 ± 0.4 2.8 ± 0.5 0.70 ± 0.12 2.4 4.0
5d -COOCH2-C≡CH 0.95 ± 0.03 1.6 ± 0.1 0.32 ± 0.06 3.0 5.0
5e graphic file with name molecules-28-04806-i005.jpg 0.47 ± 0.08 1.5 ± 0.6 0.27 ± 0.01 1.7 0.9

N.B., no binding affinity at concentrations < 30 µM.