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. Author manuscript; available in PMC: 2015 Jul 7.
Published in final edited form as: J Med Chem. 2011 Jul 8;54(15):5296–5306. doi: 10.1021/jm200543y

Table 2.

In vitro antimalarial activity of prodiginines containing alkyl substituents at the 3 and 5 positions of the terminal pyrrole ring

graphic file with name nihms-310248-t0017.jpg
Compd R1 R2 IC50 (nM)
 Cytotoxicity
(nM)
D6 Dd2
CQ - - 11 135 16057
26 n-C3H7 H 2300 N.D. N.D.
27 n-C4H9 H 1780 1590 < 125
28 n-C6H13 H 375 450 < 125
29 n-C8H17 H 80 130 < 125
30 n-C16H33 H 300 400 < 125
31 n-C11H22NH2 H 1700 N.D. N.D.
32 H (CH2)3COOCH3 4500 N.D N.D.
33 H CH2CH(CH3)2 460 230 < 125
34 H n-C4H9 80 18 < 125
35 H n-C6H13 28 7 < 125
36 H n-C8H17 4.6 1.8 < 125
37 H n-C10H21 8.0 10 < 125
38 H n-C16H33 > 25000 > 25000 3628
46 CH3 CH3 8900 8130 < 125
47 n-C6H13 n-C3H7 4.5 4.0 < 125
48 n-C8H17 n-C3H7 2.9 2.7 < 125
49 n-C3H7 graphic file with name nihms-310248-t0018.jpg 1.7 1.3 < 125
50 n-C6H13 n-C6H13 1.7 1.1 < 125
51 n-C7H15 n-C6H13 2.1 1.2 < 125
52 n-C6H13 n-C8H17 4.9 2.0 < 125
53 n-C7H15 n-C8H17 6.2 2.9 3906
54 n-C8H17 n-C8H17 92 129 31250
55 graphic file with name nihms-310248-t0019.jpg graphic file with name nihms-310248-t0020.jpg 5.3 3.5 < 125

N.D.: not determined