Cpds X Y MW OBAV, % cLogPb
2.8 NA NA 354.7 1 -0.73
5.1 Ph H 470.9 0 5.25
5.2 4-F-Ph H 488.9 2 5.30
5.3 3-Br-4-MeO-Ph H 579.8 0 5.74
5.4 3-furyl H 460.8 0 4.41
5.5 4-pyridyl H 471.9 12 3.76
5.6 2-pyridyl H 471.9 6 3.76
5.7 H CH2OH 424.8 11 2.67
5.8 H CH2OAc 466.9 10 3.57
5.9 H CH2OCO2Me 482.9 14 3.54
5.10 H CH2N3 449.8 13 3.58
5.11 H CH2NH2 423.8 4 2.72
aOBAV determined by measuring urinary excretion of 2.8 following oral administration of the prodrug vs i.v. administration of 2.8; bADME Boxes version 3.5 (Pharma Algorithm, Toronto, Canada) was used
Table 5: OBAV SAR of Phosphonate 2.8 Cyclic Ester Prodrugsa.