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. Author manuscript; available in PMC: 2011 Nov 11.
Published in final edited form as: J Med Chem. 2010 Nov 11;53(21):7699–7708. doi: 10.1021/jm1008743

Table 1.

Inhibitory Activity of Compounds against Wild-Type HIV-1 Protease and an MDR Varianta

graphic file with name nihms247035u1.jpg
Compd. R1 R2 Ki (nM)
Wt MDR
15c H 3,4-OCH2O- 0.206 5.50
15d H 3,4-S-C=N- 0.033 1.21
15e H 4-CH2OH 0.252 NT
17a 2-OH 4-NH2 7.36 40.46
17b 2-OH 4-OCH3 5.65 67.34
17c 2-OH 3,4-OCH2O- 1.47 NT
18a 2-CF3 4-NH2 0.136 5.71
18b 2-CF3 4-OCH3 0.086 2.45
18c 2-CF3 3,4-OCH2O- 0.142 4.36
18d 2-CF3 3,4-S-C=N- 0.097 1.86
18e 2-CF3 4-CH2OH 0.235 4.57
19a 2,4-di-F 4-NH2 0.385 NT
19b 2,4-di-F 4-OCH3 0.063 10.54
19c 2,4-di-F 3,4-OCH2O- 0.347 NT
19d 2,4-di-F 3,4-S-C=N- 0.150 3.50
19e 2,4-di-F 4-CH2OH 0.212 NT
20a 4-F 4-NH2 0.448 NT
20b 4-F 4-OCH3 0.128 9.57
20c 4-F 3,4-OCH2O- 0.167 10.78
20d 4-F 3,4-S-C=N- 0.133 3.0
20e 4-F 4-CH2OH 0.207 9.56
21d 4-Ac 3,4-S-C=N- 0.073 2.04
21e 4-Ac 4-CH2OH 0.317 NT
22d 3-F 3,4-S-C=N- 0.080 2.12
22e 3-F 4-CH2OH 0.319 NT
23d 3,4-di-F 3,4-S-C=N- 0.232 5.18
23e 3,4-di-F 4-CH2OH 0.330 NT
24d 3-CF3 3,4-S-C=N- 0.016 2.96
24e 3-CF3 4-CH2OH 0.196 10.15
25a 3-OCF3 4-NH2 0.225 9.95
25b 3-OCF3 4-OCH3 0.130 16.3
25c 3-OCF3 3,4-OCH2O- 0.239 10.6
25d 3-OCF3 3,4-S-C=N- 0.026 3.38
25e 3-OCF3 4-CH2OH 0.286 7.49
26d 3-Ac 3,4-S-C=N- 0.015 1.69
26e 3-Ac 4-CH2OH 0.236 NT
27b 3-SO2CH3 4-OCH3 0.049 1.74
27c 3-SO2CH3 3,4-OCH2O- 0.025 4.16
27d 3-SO2CH3 3,4-S-C=N- 0.003 2.45
28b 3-NO2 4-OCH3 0.136 5.40
28c 3-NO2 3,4-OCH2O- 0.117 6.48
28d 3-NO2 3,4-S-C=N- 0.015 0.93
29b 3-NH2 4-OCH3 0.020 2.68
29c 3-NH2 3,4-OCH2O- 0.113 6.55
29d 3-NH2 3,4-S-C=N- 0.008 1.84
30b 3-NHAc 4-OCH3 0.122 3.89
30c 3-NHAc 3,4-OCH2O- 0.051 4.76
30d 3-NHAc 3,4-S-C=N- 0.006 2.83
31b 3-NHCO2CH3 4-OCH3 0.163 4.44
31c 3-NHCO2CH3 3,4-OCH2O- 0.289 3.68
31d 3-NHCO2CH3 3,4-S-C=N- 0.026 1.87
LPV 0.005 0.90
DRV 0.008 0.025

Wt: Q7K; MDR: L10I, L63P, A71V, G73S, I84V, L90M. NT = not tested