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. 2019 Oct 22;11:70–79. doi: 10.1016/j.ijpddr.2019.10.004

Table 1.

Structures and bioactivity data for terpenyl-quinone/hydroquinone derivatives obtained from myrcene.

Comp. Type R R1 R2 EC50 (μM)
 CC50 (μM)
 SIp SIa IC50 (μM)
L. infantum promastigotes L. infantum amastigotes Human HepG2 Leishmanial
TopIB
1 NQ I Cl Image 3 22.8 ± 0.6 >100 50.1 ± 2.4 2.2 <0.50 23.5 ± 1.3
2 NQ I Br Br 11.7 ± 0.1 90.0 ± 4.3 14.7 ± 0.8 1.3 0.16 13.5 ± 0.6
3 NQ I Br Image 4 >100 12.8 ± 1.5 160 ± 12 <1.6 12 >100
4 NQ I Image 5 H 0.57 ± 0.04 7.74 ± 0.07 10.8 ± 0.8 18.9 1.4 50.1 ± 5.0
5 NQ II Cl H 18.8 ± 0.6 >100 104 ± 8 5.5 <1.0 >100
6
 NQ
 II
 Cl
 Image 6
 11.4 ± 0.5
 28.8 ± 1.4
 131 ± 6
 11.5
 4.5
 73.5 ± 3.4
7 NHQ II H H 7.19 ± 0.17 7.18 ± 0.28 4.33 ± 0.28 0.6 0.60 >100
8 NHQ II CH3 H 12.7 ± 0.3 5.71 ± 0.59 28.0 ± 1.2 2.2 4.9 >100
9 NHQ II OCH3 H 15.3 ± 0.3 50.3 ± 0.3 28.6 ± 1.3 1.9 0.57 >100
10 NHQ (5,8-dihydro) II CH3 H 10.9 ± 0.5 3.61 ± 0.69 > 200 >18.3 > 55 >100
11
 NHQ
 Image 7
 H
 H
 6.19 ± 0.03
 17.8 ± 1.2
 7.66 ± 0.26
 1.2
 0.43
 >100
12 1,4-AQ – H H 1.20 ± 0.08 23.0 ± 2.1 13.4 ± 1.3 11.2 0.58 10.7 ± 2.2
13 1,4-AQ – OCH3 H 7.56 ± 0.14 14.2 ± 2.5 29.7 ± 1.3 3.9 2.1 91.8 ± 8.2
14 1,4-AQ – OEt H 16.1 ± 0.8 14.8 ± 1.9 199 ± 14 12.4 13 >100
15 1,4-AQ – NHEt H 19.9 ± 1.7 33.8 ± 5.2 149 ± 9 7.5 4.4 >100
16 1,4-AQ – NHEt Cl 12.5 ± 0.0 66.6 ± 3.3 > 200 16.0 >3.0 >100
17
 1,4-AQ
 –
 Image 8
 H
 13.5 ± 0.4
 16.3 ± 2.1
 > 200
 14.8
 > 12
 >100
18 1,4-AHQ (9,10-dihydro) – H H 15.9 ± 1.1 1.22 ± 0.01 37.0 ± 2.1 2.3 30 >100
19 1,4-AHQ – H H 3.3 ± 0.1 2.64 ± 0.01 5.94 ± 0.31 1.8 2.3 >100
20
 1,4-AHQ
 –
 OCH3
 H
 16.6 ± 0.4
 19.3 ± 1.6
 54.6 ± 5.3
 3.3
 2.8
 >100
21 9,10-AQ II H H 18.2 ± 1.1 21.5 ± 1.1 57.8 ± 1.7 3.2 2.7 57.9 ± 4.1
22 9,10-AQ Image 9 H H 57.5 ± 0.2 44.8 ± 1.6 147 ± 11 2.5 3.3 >100
23 9,10-AQ (4a,9a-dihydro) II H H 69.6 ± 8.4 >100 82.9 ± 5.3 1.2 >0.83 >100
24 9,10-AQ (4a,9a-dihydro) Image 10 H H 85.4 ± 2.5 21.6 ± 2.4 >200 2.3 >9.3 >100
25
 BAcQ
 Image 11
 39.0 ± 4.3
 24.9 ± 0.30
 124 ± 8
 3.2
 5.0
 41.4 ± 7.4
MTF 5.9 ± 1.4 2.40 ± 0.21 50.4 ± 4.3 8.5 21 nt
AMB 0.77 ± 0.15 0.32 ± 0.05 nt un un nt

2.1.

SIp: Selectivity Index for promastigotes (CC50 HepG2/EC50 promastigotes); SIa: Selectivity Index for amastigotes (CC50 HepG2/EC50 amastigotes); MTF: Miltefosine; AMB: Amphotericin B deoxycholate; nt: not tested; un: undefined. Significant values (EC50: ≤10 μM, SI: ≥ 10, and CC50 ≥ 100 μM) are bolded for comparison purposes.