Cpds R MW OBAV, % cLogPb
2.8 H 354.7 1 -0.73
4.1 -(CH2)2COPh 683.2 0 8.06
4.2 -CH2Ph-(3-Cl-4-OAc) 663.9 0 7.89
4.3 -CH2Ph-(3,4-di-OAc) 767.1 1 3.61
4.4 -CH2Ph-(3-Me-4-OAc) 679.1 1 6.56
4.5 -CH2Ph-(3-OMe-4-OAc) 711.1 1 5.29
4.6 -CH2Ph-(3-Br-4-OMe) 752.8 1 7.94
4.7 -CH2OCOOPh-(2-Me) 683.0 1 7.17
4.8 -CH2OCOBu-t 583.0 0 6.07
4.9 -CH2OCOPr-i 555.0 1 5.37
4.10 -CH2OCOPh 623.0 1 7.65
4.11 -CH2SCOPh 655.1 1 7.73
4.12 -CH2OCOPh-(4-F) 659.0 0 7.82
4.13 -CH2OCO(3-furyl) 602.9 1 5.81
4.14 -CH2OCO(2-furyl) 602.9 1 5.24
4.15 -CH2OCO(2-thienyl) 635.0 1 6.86
4.16 -CH2OCO[3-pyridyl-(6-Cl)] 693.9 1 6.31
4.17 -CH2OCO[3-pyridyl-(6-Br)] 782.8 0 6.59
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 4: OBAV SAR of Phosphonate 2.8 Diester Prodrugsa.