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. Author manuscript; available in PMC: 2013 Jun 14.
Published in final edited form as: J Med Chem. 2012 May 23;55(11):5554–5565. doi: 10.1021/jm300508n

Table 1.

In vitro biological and physical properties of 3-nitrotriazole-based amides/sulfonamides.

Comp. T.b.rhod.a SI T. cruzib SI L.don. ax.c SId L6e IC50 Bnz/IC50 Comp logP PSA Chemical Structure
IC50 (μM) IC50 (μM) IC50(μM) IC50 (μM) (Å2)
Melars. 0.012 Reference
Bnz 1.562 Reference
Miltef. 0.382 Reference
Podoph. 0.022 Reference
1 21.374 6.053 29 13.77 176.6 0.3 2.52 92.74 graphic file with name nihms376965t1.jpg
2 46.648 3.715 74 36.03 274 0.4 3.07 102 graphic file with name nihms376965t2.jpg
3 3.161 0.438 >625 33.44 >273.6 3.6 2.09 105.6 graphic file with name nihms376965t3.jpg
4 0.501 208 0.176 591 7.93 104.3 8.9 2.66 105.6 graphic file with name nihms376965t4.jpg
5 1.986 >131 0.73 >357 29.25 >260.9 2.1 2.64 114.9 graphic file with name nihms376965t5.jpg
6 1.391 >193 0.113 >2381 12.98 >268 13.8 3.22 114.9 graphic file with name nihms376965t6.jpg
7 3.761 0.353 >826 37.32 >292 4.4 2.15 105.6 graphic file with name nihms376965t7.jpg
8 16.4 11.4 0.642 290.7 12.34 186.6 2.4 3.03 105.6 graphic file with name nihms376965t8.jpg
9 3.546 3.459 >84 96.51 >291 0.5 1.32 118.5 graphic file with name nihms376965t9.jpg
10 3.22 0.138 1579 19.94 217.98 11.3 1.81 118.5 graphic file with name nihms376965t10.jpg
11 4 0.132 691 13.41 91.5 11.8 2.33 118.5 graphic file with name nihms376965t11.jpg
12 34.862 0.807 >379 62.69 >306 1.9 0.98 131.4 graphic file with name nihms376965t12.jpg
13 0.587 199 0.043 2782 8.37 117 36.3 2.92 105.6 graphic file with name nihms376965t13.jpg
14 9.96 3.383 102 28.12 344.83 0.5 0.95 105.6 graphic file with name nihms376965t14.jpg
15 6.474 0.970 133 10.39 128.88 1.6 1.83 105.6 graphic file with name nihms376965t15.jpg
16 3.404 0.307 468 51.37 143.77 5.1 2.17 96.84 graphic file with name nihms376965t16.jpg
17 11.51 14.8 1.799 94.4 5.91 28.7 169.8 0.9 2.58 118.5 graphic file with name nihms376965t17.jpg
18 48.45 3.4 6.588 24.8 5.82 28 163.1 0.2 2.67 118.5 graphic file with name nihms376965t18.jpg
19 34.42 <1 7.876 3.3 4.68 5.6 26.3 0.2 1.88 131.66 graphic file with name nihms376965t19.jpg
20 6.03 4 0.734 33 11.43 24.18 2.1 3.08 117.66 graphic file with name nihms376965t20.jpg
21 27.51 1.659 106 15.55 175.99 0.9 2.27 109.81 graphic file with name nihms376965t21.jpg
22 2.79 0.803 248.5 32.38 199.5 1.9 1.84 122.70 graphic file with name nihms376965t22.jpg
23 0.504 467 0.359 656 13.09 235.33 4.4 1.9 122.70 graphic file with name nihms376965t23.jpg
24 0.354 240 0.71 120 7.79 84.91 2.2 2.42 122.70 graphic file with name nihms376965t24.jpg
25 10.313 0.644 178 46.09 114.77 2.4 2.78 122.70 graphic file with name nihms376965t25.jpg
26 36.7 3 1.677 66.2 33.26 111.1 0.9 2.72 122.70 graphic file with name nihms376965t26.jpg
27 11.3 9.6 0.322 337.6 20.74 108.7 4.9 2.78 122.70 graphic file with name nihms376965t27.jpg
28 2.54 121 0.412 >746.8 38.15 >8.1 >307.7 3.8 1.54 122.70 graphic file with name nihms376965t28.jpg
29 0.477 234.9 0.203 551.7 7.8 14.4 112 7.7 2.97 131.93 graphic file with name nihms376965t29.jpg
30 8.39 >38.3 6.463 >48 112.86 >321.5 0.2 0.73 122.70 graphic file with name nihms376965t30.jpg
31 6.49 >47.4 2.237 >137.6 79.38 >307.7 0.7 0.79 122.70 graphic file with name nihms376965t31.jpg
32 35.88 >9.3 83.39 4 >332.2 >332.2 0.0 −0.25 140.52 graphic file with name nihms376965t32.jpg
33 21.9 >14.5 20.57 >15 223.17 >317.5 0.1 −0.19 140.52 graphic file with name nihms376965t33.jpg
34 1.99 122 0.438 556 33 7.4 243.5 3.6 1.74 122.70 graphic file with name nihms376965t34.jpg
35 1.049 0.028 1764 7.54 50 55.8 2.67 122.70 graphic file with name nihms376965t35.jpg
36 6.519 0.4 519 32.87 208 3.9 1.18 135.59 graphic file with name nihms376965t36.jpg
active moderately active active but cytotoxic, low specificity
a

T.b. rhodesiense, strain STIB 900 trypomastigotes;

b

T. cruzi, strain Tulahuen C4 amastigotes;

c

L. donovani axenic, strain MHOM-ET-67/L82 amastigotes;

d

SI is the ratio: IC50 in L6 cells/IC50 in each parasite.

e

Cytotoxicity in L6 cells. Reference drugs: Melarsoprol (Melars), Benznidazole (Bnz), Miltefosine (Miltef), Podophylotoxin (Podoph). The IC50 value of each reference is the mean from 36 measurements in parallel with each compound (SD was 0.001, 0.011 and 0.005 for Melars, Bnz and Miltef, respectively). PSA: polar surface area; All physical properties were predicted by using the Marvin Calculator (www.chemaxon.com).