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. 2012 Feb 15;20(4):1607–1615. doi: 10.1016/j.bmc.2011.12.018

Table 1.

Quinol analogues and their inhibitory activities against T. brucei and MRC5 cells

graphic file with name fx2.jpg

Core Compd Structure
 EC50T. brucei (μM)a (SD, n) EC50 MRC5 (μM)a (SD, n) Spec. selectb log Pc
R1 R2 R3 X Y
A 1 Ethynyl H H n/a n/a 2.0 (0.80, 4) 2.1 (0.15, 4) 1 0.76
A 2 Phenyl H H n/a n/a 0.75d 1.7d 2 1.3
n/a 3 n/a n/a n/a n/a n/a 2.2 (0.0017, 2) 0.67 (0.088, 2) 0.3 3.3



Benzothiazoles
A 4e 2-Benzo[d]thiazole H H n/a n/a 0.077d 0.18d 2 1.8
A 5 2-Benzo[d]thiazole CH3 H n/a n/a 0.33d 1.1d 3 2.7
A 6 2-Benzo[d]thiazole H Cl n/a n/a 0.046 (0.0067, 2) 0.055 (0.037, 4) 1 1.9
n/a 7 n/a n/a n/a n/a n/a >50d >50d n/a 3.5



Triazoles
B 8 4-Methoxyphenyl n/a n/a n/a n/a 0.13d 0.31d 2 0.75
B 9 4-Methoxybenzyl n/a n/a n/a n/a 0.16 (0.054, 4) 0.45 (0.12, 4) 3 1.1
B 10 6-Benzo[d]thiazole n/a n/a n/a n/a 0.027 (0.0018, 2) 0.069 (0.017, 4) 3 1.5
B 11 1-(β-d-Galactopyranosyl, 2,3,4,6-tetraacetate) n/a n/a n/a n/a 10 (6.2, 4) >50 (n/a, 3) >5 −0.30
B 12 CH2CH2CONHPh n/a n/a n/a n/a 2.7 (0.084, 2) 18 (2.0, 2) 7 0.77



Indolyls
C 13 H n/a n/a CH CF 0.10d 0.17d 2 2.3
C 14 H n/a n/a CH CH 0.053d 0.11d 2 2.3
C 15 H n/a n/a N CH 0.022 (0.0026, 4) 0.041 (0.021, 4) 2 1.4
C 16 CH3 n/a n/a CH N 0.026 (0.0065, 4) 0.044 (0.028, 4) 2 1.8
C 17 NHCO2Et n/a n/a CH CH 0.050 (0.016, 4) 0.086 (0.029, 4) 2 2.3
C 18 CH2CH2NHAc n/a n/a CH CH 0.012 (0.0019, 2) 0.036 (0.0064, 4) 3 1.9
C 19 CH2CH2CO2CH3 n/a n/a CH CH 0.16 (0.066, 14) 0.28 (0.14, 13) 2 2.4
C 20 CH2CH2CH2OH n/a n/a CH CH 0.024 (0.0017, 2) 0.051 (0.015, 4) 2 2.1
C 21 CH2CH2CO-N-morpholine n/a n/a CH CH 0.036 (0.0097, 4) 0.067 (0.014, 4) 2 1.5
C 22 CH2CH2CO-4-(1-methylpiperazine) n/a n/a CH CH 0.018 (0.0032, 6) 0.052 (0.022) 3 1.6
C 23 CH2CH2CH2-N-morpholine n/a n/a CH CH 0.026 (0.00042, 2) 0.079 (0.043, 4) 3 2.5
C 24 CH2CH2CH2-4-(1-methylpiperazine) n/a n/a CH CH 0.016 (0.0063, 4) 0.050 (0.023, 4) 3 2.6
C 25 SO2CH3 n/a n/a CH CH 0.024 (0.0017, 4) 0.039 (0.0072, 4) 2 1.5

n/a is not applicable.

a

The EC50 values are the arithmetic mean of independent determinations with the standard deviations (SD) followed by the number of repeats (n) given in parentheses.

b

Species selectivity (Spec. select.) is defined as EC50 (MRC5)/EC50 (T. brucei).

c

Calculated log P values generated using the software package StarDrop by Optibrium.24

d

Data taken from Konig et al.21

e

Previously published as PMX 464.