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. Author manuscript; available in PMC: 2010 Sep 1.
Published in final edited form as: Bioorg Med Chem Lett. 2009 Jul 10;19(17):5101–5104. doi: 10.1016/j.bmcl.2009.07.035

Table 1.

Synthesis and in vitro reactivation potency of monoquaternary pyridinium oximes 5–35 for paraoxon-inhibited EeAChE and rHuAChE

graphic file with name nihms135456t1.jpg
Entry R Oxime
position		 X Reaction
time (h)		 %
Yield		 % Reactivation = [(Ar-Ai)/(Ao-Ai)] × 100
EeAChE (% R ± SEM) rHuAChE (% R ± SEM)
10−3 Ma 10−4 Ma 10−5 Ma 10−3 Ma 10−4 Ma 10−5 Ma
1 H 2 I - - 67 ± 1 67 ± 3 63 ± 3 42 ± 2 22 ± 2 7 ± 1
5 CONH2 2 I 24 62 41 ± 3 9 ± 0 1 ± 0 2 ± 1 2 ± 0 1 ± 0
6 CONH2 3 I 2 76 1 ± 1 0 0 0 1 ± 0 2 ± 0
7 CONH2 4 I 2 84 44 ± 2 6 ± 1 0 0 1 ± 0 1 ± 0
8 COOH 2 I 24 61 45 ± 3 36 ± 3 34 ± 2 15 ± 1 15 ± 2 5 ± 1
9 COOH 3 I 2 71 1 ± 0 0 0 0 1 ± 0 1 ± 0
10 COOH 4 I 2 78 4 ± 0 0 0 0 1 ± 0 2 ± 0
11 CH2OH 2 Br 24 58 50 ± 4 37 ± 3 13 ± 1 2 ± 2 5 ± 0 2 ± 0
12 CH2OH 3 Br 2 60 8 ± 1 0 0 ± 0 0 1 ± 0 1 ± 0
13 CH2OH 4 Br 2 68 70 ± 2 2 ± 2 3 ± 1 6 ± 1 3 ± 0 2 ± 0
14 CH2COOH 2 Br 24 48 10 ±1 0 0 0 1 ± 0 1 ± 0
15 CH2COOH 3 Br 2 56 5 ± 0 0 0 0 1 ± 0 1 ± 0
16 CH2COOH 4 Br 2 68 15 ±1 0 0 0 2 ± 0 1 ± 0
17 4-methoxybenzen-1-yl 2 Cl 12 70 8 ± 1 19 ± 2 18 ± 2 0 7 ± 1 3 ± 0
18 4-methoxybenzen-1-yl 3 Cl 1 84 1 ± 1 0 0 0 3 ± 0 2 ± 0
19 4-methoxybenzen-1-yl 4 Cl 1 92 19 ± 1 11 ± 1 3 ± 1 0 3 ± 1 2 ± 0
20 thiophen-2-yl 2 Cl 24 58 1 ± 0 24 ± 2 34 ± 2 0 9 ± 2 9 ± 1
21 thiophen-2-yl 3 Cl 2 65 0 3 ± 1 1 ± 0 0 4 ± 0 5 ± 0
22 thiophen-2-yl 4 Cl 2 78 3 ± 0 12 ± 2 12 ± 0 0 4 ± 1 5 ± 0
23 5-bromothiophen-2-yl 2 Cl 12 74 0 29 ± 2 37 ± 2 0 7 ± 0 8 ± 1
24 5-bromothiophen-2-yl 3 Cl 1 84 4 ± 1 7 ± 0 8 ± 1 0 5 ± 1 6 ± 0
25 5-bromothiophen-2-yl 4 Cl 1 90 3 ± 1 14 ± 1 10 ± 1 0 5 ± 1 4 ± 0
26 benzthiophen-3-yl 2 Cl 24 67 0 28 ± 2 24 ± 3 0 7 ± 1 8 ± 1
27 benzthiophen-3-yl 3 Cl 2 79 0 5 ± 1 8 ± 1 0 2 ± 0 5 ± 1
28 benzthiophen-3-yl 4 Cl 2 85 0 0 1 ± 1 0 2 ± 0 2 ± 0
29 thiophen-3-yl 2 Cl 24 79 0 8 ± 1 28 ± 2 0 2 ± 0 5 ± 1
30 furan-2-yl 3 Cl 1 62 0 0 0 0 2 ± 0 2 ± 0
31 furan-2-yl 4 Cl 1 60 8 ± 1 14 ± 2 1 ± 1 0 3 ± 0 2 ± 0
32 furan-3-yl 3 Cl 1 46 0 0 0 0 3 ± 0 2 ± 0
33 3-methyl-isoxazol-5-yl 2 Br 24 40 7 ± 1 25 ± 3 8 ± 1 0 7 ± 1 3 ± 0
34 3-methyl-isoxazol-5-yl 3 Br 2 64 0 0 0 0 3 ± 1 2 ± 0
35 3-methyl-isoxazol-5-yl 4 Br 2 67 20 ± 2 24 ± 2 6 ± 0 0 2 ± 1 2 ± 0
*

compounds 5–16 acetone, 60–70 °C, 2–24 h; 17–35 MeCN, 70–80 °C, 2–24 h;

a

reactivator concentration