Table 4.
Cytotoxicity against MT-4, MDBK, BHK and Vero-76 cell lines and BVDV, YFV, Reo-1, CVB-2, RSV, HSV-1 and Sb-1 inhibitory activity of 1,3-diaryltriazenes of structure D and E
| Compda | X | R | R′ | MT-4 CC50b | MDBK CC50c | BVDV EC50d | BHK-21 CC50e | YFV EC50f | Reo-1 EC50g | VERO-76 CC50h | CVB-2 EC50i | RSV EC50j | HSV-1 EC50k | Sb-1 EC50l |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 13 | H | H | H | 47 | >100 | >100 | >100 | >100 | >100 | 90 | >90 | ⩾90 | >90 | >90 |
| 14 | H | H | 3-CF3 | >100 | >100 | >100 | >100 | ⩾100 | >100 | 15 | 8 | 3 | >15 | >15 |
| 15 | H | H | CH2-Phm | 42 | >100 | >100 | >100 | >100 | >100 | 100 | >100 | >100 | >100 | >100 |
| 16 | H | 3-NO2 | H | 40 | 94 | 19 | 38 | >38 | >38 | 33 | >33 | >33 | >33 | >33 |
| 17 | H | 3-NO2 | 3-NO2 | >100 | >100 | >100 | >100 | >100 | >100 | >100 | >100 | >100 | >100 | >100 |
| 18 | H | 2,5-diF | H | 100 | >100 | >100 | >100 | >100 | >100 | 80 | 12 | 10 | 55 | >80 |
| 19 | H | 2,5-diF | 3-CF3 | >100 | >100 | >100 | >100 | 80 | >100 | 80 | >80 | 10 | >80 | >80 |
| 20 | H | 2,5-diF | 2,5-diF | ⩾100 | >100 | >100 | >100 | >100 | >100 | ⩾100 | 50 | 8 | >100 | >100 |
| 21 | CH3 | H | H | 55 | >100 | >100 | >100 | >100 | >100 | 50 | >50 | 20 | >50 | >50 |
| 22 | CH3 | H | CH2-Phm | ⩾100 | >100 | >100 | >100 | >100 | >100 | ⩾100 | >100 | >100 | >100 | >100 |
| 23 | CH3 | 3-NO2 | H | >100 | 82 | >82 | >100 | >100 | 33 | >100 | >100 | 15 | >100 | 29 |
| 24 | CH3 | 4-CH3 | H | 45 | >100 | >100 | >100 | >100 | >100 | 58 | >58 | >58 | >58 | >58 |
| 25 | (CH2)3-NMe2 | H | H | 33 | 95 | ⩾95 | 50 | >50 | >50 | 35 | 6 | >35 | 12 | >35 |
| 26 | (CH2)3-NMe2 | H | 3-CF3 | 14 | 38 | >38 | 49 | ⩾49 | >49 | 20 | ⩾20 | >20 | 14 | >20 |
| 27 | (CH2)3-NMe2 | 3-NO2 | H | 14 | 37 | >37 | 54 | 24 | >54 | 40 | >40 | >40 | 30 | >40 |
| 28 | (CH2)3-NMe2 | 4-NO2 | H | 20 | 39 | ⩾39 | 36 | ⩾36 | >36 | 40 | >40 | >40 | >40 | >40 |
| 29 | (CH2)3-NMe2 | 2,5-diF | H | 13 | 25 | >25 | 25 | >25 | >25 | 7 | >7 | >7 | >7 | >7 |
| 30 | (CH2)3-NMe2 | 2,5-diF | 3-CF3 | 16 | >100 | 90 | 54 | >54 | >54 | 30 | >30 | >30 | >30 | >30 |
| 31 | (CH2)3-NMe2 | 2,6-diF | H | 23 | 45 | >45 | 52 | 20 | >52 | 25 | 9 | ⩾25 | 12 | >25 |
| 32 | (CH2)3-NMe2 | 4-CH3 | H | 18 | >100 | >100 | >100 | >100 | >100 | 100 | >100 | >100 | >100 | >100 |
| 33 | Lupinyln | H | 3-CF3 | 17 | 22 | >22 | 40 | 23 | >40 | 75 | >75 | >75 | >75 | >75 |
| NM 108 | >100 | >100 | 1.7 | 90 | 1.8 | 2.4 | >100 | 20 | >100 | >100 | >100 | |||
| NM 299 | 2 | >100 | >100 | >100 | 26 | >100 | 20 | >20 | 1.2 | >20 | >20 | |||
| ACG | >100 | >100 | >100 | >100 | >100 | >100 | >100 | >100 | >100 | 3 | >100 | |||
| Ribavirin | 31 | >100 | 7 | >100 | >100 | >100 | >100 | >100 | 7 | >100 | >100 | |||
| NM 176 | ⩾100 | >100 | 38 | >100 | >100 | >100 | >100 | 24 | >100 | >100 | 20 | |||
| M 5255 | 0.2 | 42 | >42 | >100 | >100 | >100 | ⩾13 | >13 | 0.6 | >13 | >13 |
a
None of compounds 13–33 inhibited the multiplication of HIV-1, VSV and VV viruses.
b-k
For the meaning see Table 3.
l
Compound concentration (μM) required to reduce the plaque number of Sb-1 (Poliovirus Type-1, Sabin strain) by 50% in Vero-76 monolayers.
m
In compounds 15 and 22 the R′-substituted phenyl ring is replaced by a benzyl residue.
n
(1S,9aR-Octahydro-2H-quinolizin-1-yl)methyl.