Table 1

Physicochemical parameters of Cinchona alkaloids. cpd. = compound, VAR = calculated vacuolar accumulation ratio. S = chloroquine-sensitive, R = chloroquine-resistant. S/R = ratio of IC50 values. BHIA = % inhibition in β-haematin inhibition test
Cpd.
 pKa1
 pKa2
 Log P
 Log D (pH7.4)
 Log D (pH5.2)
 VAR
 IC50 nM S
 IC50 nM R
 RATIO S/R
 BHIA % inhib.
Q
 8.58a
 4.12b
 3.17c
 1.97e
 0.30
 161.0
 29.315
 103.215
 0.28
 84 ± 1



2.79d
 1.96f
 -0.25f




QD
 8.58g
 4.42h
 2.84i
 1.66j
 0.40k
 173.2
 13.415
 43.715
 0.31
 85 ± 9



2.79d
 1.63f
 -0.61f




HQ
 9.01 l
 4.29
 3.07
 1.50
 0.53
 173.6
 21.315
 151.715
 0.14
 93 ± 0.6



3.27d
 1.45f
 -0.79f




HQD
 9.16
 4.34
 3.43
 1.72
 0.75
 177.5
 10.415
 74.115
 0.14
 95 ± 0.4



3.27d
 1.66f
 -0.59f




C
 8.35m
 4.28n
 2.82o
 1.85p
 -0.38f
 159.6
 18.346
 70.846
 0.26
 94 ± 0.5



2.49d
 1.82f





CD
 8.40q
 4.17r
 2.68s
 1.73t
 -0.56f
 157.5
 69.546
 206.846
 0.34
 94 ± 0.4



2.49d
 1.64f





EQ
 9.54u
 4.08
 2.90
 0.76
 -1.44
 169.2
 347115
 117915
 2.94
 2 ± 13



2.79d
 0.76f
 -1.47f




EQD
 9.39v
 4.15
 2.53
 0.55
 -1.2
 170.8
 270015
 102415
 2.64
 12 ± 12



2.79d
 0.54f
 -1.70f




CQ
 10.18
 8.38
 4.72
 0.96
 -3.44
 22750
 18.5
 264
 0.07
 81 ± 15




0.92f
 -3.44f




VE
 8.462
 <0
 3.7962
 2.75f
 0.59f
 144.2
 720053
 250053
 2.88
 0 ± 21
PMZ
 9.1142
 <0
 4.7542
 3.03f
 0.84f
 155.5
 143652
 83552
 1.70
 15 ± 22.5

a: Lit 8.43[64], 8.4[39], 8.05[65], 8.59[66]. In 80% methylcellosolve/20% water 7.73[41], 7.25[67] ; b: Lit. 4.34[64],4.32 [39], 4.33 [66]. In 80% methylcellosolve 2.81[67], 2.38[68] ; c: Lit. 3.44[22], 2.64[65] ; d: Calc. from CLogP ; e: Lit. 1.90[65], 2.14[22], 2.54[69], 1.73(pH7.0)[70] ; f: Calc from eqn. (1). ; g: Lit. 8.79[64], 7.95[41], 8.78[42]. In 80% methylcellosolve 7.95[41]7.36[67] ; h: Lit. 4.34[64], in 80% methylcellosolve 2.66[67], 2.40[68] ; i: Lit: 2.88[65], 3.71[42] ; j: Lit. 2.03[72], 2.07[74],2.11[31], 2.22[65]; k: Lit: -0.07[42] ; l: Lit. 8.87[40] ; m: Lit. 8.35[40], 8.32[65]. In 80% methylcellosolve 7.36[68] ; n: Lit. 4.28[67], In 80% methylcellosolve 2.80[67], 2.15[68] ; o: Lit 2.82[65]; p: Lit 1.85[65] ; q: Lit. 8.40[40], 8.30[65]; r: Lit. 4.17[40]. In 80% methylcellosolve 2.66[67], 2.12[68] ; s: Lit. 2.68[65] ; t: Lit. 1.73[65] ; u: Lit. In 80% methylcellosolve 8.44[41] ; v: Lit. in 80% methylcellosolve 8.32[41].

Warhurst et al. Malaria Journal 2003 2:26   doi:10.1186/1475-2875-2-26