Table 3.
Apparent bimolecular rate constants ki for inactivation of AgAChE and hAChE by 3-substituted aryl methylcarbamates
| Cpd | R3 | AgAChEa ki (mM−1 min−1) | hAChEb ki (mM−1 min−1) | Ag/h selectivityc |
|---|---|---|---|---|
| 20h | -CH3 | 17.2 ± 0.3 | 0.52 ± 0.08 | 33 ± 5 |
| 20i | -Pr | 881 ± 17 | 63.7 ± 1.9 | 14.0 ± 0.5 |
| 20j | -Bu | 741 ± 5 | 32.1 ± 0.6 | 23.0 ± 0.5 |
| 20k | -i-Pr | 3,270 ± 70 | 383 ± 19 | 8.5 ± 0.5 |
| 20l | -s-Bu (±) | 10,000 ± 100 | 1,910 ± 110 | 5.3 ± 0.4 |
| 20m | -t-Bu | 1,510 ± 110 | 126 ± 3 | 12 ± 1 |
| 20n | -CMe2CF3 | 1,580 ± 40 | 139 ± 6 | 11 ± 0.6 |
| 20o | -CMe2Et | 7,600 ± 300 | 784 ± 28 | 9.7 ± 0.5 |
| 20p | -CMe(CF3)Et (±) | 3,270 ± 70 | 375 ± 6 | 8.7 ± 0.2 |
| 20q | -CMe2Pr | 6,690 ± 240 | 1,360 ± 40 | 4.9 ± 0.2 |
| 20r | -CMeEt2 | 5,280 ± 170 | 553 ± 13 | 9.5 ± 0.4 |
| 20s | -SiMe3 | 648 ± 29 | 67.8 ± 2.6 | 9.6 ± 0.6 |
| 20t | -SiMe2Et | 1,510 ± 70 | 110 ± 6 | 14 ± 1 |
| 20u | -CH2CHMe2 | 155 ± 6 | 5.5 ± 0.30 | 28 ± 2 |
| 20v | -OCH2CHEt2 | 28.8 ± 0.4 | 5.0 ± 0.6 | 5.8 ± 0.7 |
| 20w | -(CH2)2CHMe2 | 272 ± 10 | 5.2 ± 2 | 53 ± 3 |
a
Recombinant AgAChE purified to 2,500 ± 100 U/mg (Supporting Information).
b
Commercial recombinant hAChE (Sigma C1682).
c
Defined as ki(Ag)/ki (h); error in ratio calculated by standard propagation of error.