Skip to main content

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

From: The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids

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
  1. 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].