Arch. Pharm. Chem. Life Sci. 2007, 340, 315–319
Table 1. Spectral data of compounds 4–9.
3-Arylazo-5-phenyl-2(3H)-furanones
317
No.
IR (mmax) KBr(cm– 1
)
1H–NMR (DMSO–d6)
mNH
mC=O
mC=S
4a
4b
3353–3280
1685
1648
2.8–3.2 (s, 2H, –CH2), 3.9 (s, 2H, NH2 exchangeable), 6.7–7.4 (m, 11H, 2
Ar-H + NHCO– exchangeable), 9.6 (s, 1H, NH-Ar exchangeable)
3340–3275
3255–3280
1689
1655
2.75–3.2 (s, 2H, –CH2), 3.85(s, 2H, NH2 exchangeable), 6.75 (s, 1H,
NHCO– exchangeable), 7.1–7.45 (m, 9H, Ar-H), 9.75 (s, 1H, NH-Ar ex-
changeable)
4c
1676
1651
2.9–3.2 (s, 2H, –CH2), 3.8 (s, 3H, –OCH3), 4.4 (br, 2H, NH2 exchangeable),
6.85 (d, 2H, Ar-H), 7.11 (d, 2H, Ar-H), 7.23 (s, 1H, NHCO– exchangeable),
7.31–7.41(m, 5H, Ar-H), 9.43 (s, 1H, NH-Ar exchangeable)
5a
5b
5c
3209–3213
3206–3220
3338–3340
1685
1676
1693
7.15 (s,1H, Pyrazole H),7.2–7.6 (m, 13H, 3 Ar–H), 7.9 (m, 2H, Ar-H), 10.3
(s,1H, NH exchangeable), 10.45 (s, 1H, NH exchangeable)
7.15 (s, 1H, Pyrazole H), 7.25–7.6 (m, 12H, Ar-H), 7.9 (m, 2H, Ar-H), 10.4
(s, 1H, NH exchangeable), 10.6 (s, 1H, NH exchangeable)
3.75 (s,3H, –OCH3), 6.9 (d, 2H, Ar-H) 7.05 (s, 1H, pyrazole H), 7.25 (m, 7H,
Ar-H), 7.5 (m, 3H, Ar-H), 7.7 (m, 2H, Ar-H), 10.2 (s, 1H, NH exchangeable),
10.45 (s, 1H, NH exchangeable)
6a
6b
7.3–7.5 (m, 8H, pyrazole H + 7Ar-H), 7.6 (m, 3H, Ar-H), 8.2 (m, 2H, Ar-H).
7.1 (d, 2H, Ar-H), 7.3–7.5 (m, 8H, pyrazole H + Ar-H), 7.7 (m, 3H, Ar-H), 8.2
(m, 2H, Ar-H)
6c
7a
7b
7c
8a
8b
8c
9a
9b
9c
3.75 (s, 3H, –OCH3), 7.0 (d, 2H, Ar-H) 7.2–7.4 (m, 8H, pyrazole H + Ar-H),
7.6 (m, 3H, Ar-H), 8.1 (m, 2H, Ar-H)
3292–3199
3292–3199
3322–3223
3076–3100
3084–3105
3085–3104
3077–3110
3095–3115
3076–3114
1655
1649
1648
1250
1255
1252
1250
1250
1254
1250
1251
1250
7.11 (s, 1H, Pyrazole H), 7.2–7.5(m, 15H, Ar-H), 9.75 (br, 2H, NH ex-
changeable), 10.37 (s, 1H, NH exchangeable)
7.2 (s, 1H, Pyrazole H), 7.3–7.9 (m, 14H, Ar-H), 9.8 (br, 2H, NH exchange-
able), 10.4 (s ,1H, NH exchangeable)
3.77 (s, 3H, –OCH3), 7.1 (s, 1H, Pyrazole H),7.35–7.8 (m, 14H, Ar-H), 9.9
(br, 2H, NH exchangeable), 10.4 (s, 1H, NH exchangeable)
6.60 (s, 1H, Pyrazole H) ,6.9–7.56 (m, 15H, Ar-H), 14.16 (br, 1H, NH ex-
changeable)
6.75 (s, H, Pyrazole H), 7.0–7.7 (m, 14H, Ar-H), 13.75 (br, 1H, NH ex-
changeable)
3.8 (s, 3H, –OCH3), 6.8 (s, 1H, Pyrazole H) ,7.15–7.75 (m, 15H, Ar-H),
14.16 (br, 1H, NH exchangeable)
7.19 (s, 1H, Pyrazole H), 7.2–7.4 (m, 10H, Ar-H), 14.7 (br, 1H, NH ex-
changeable)
7.15 (s, 1H, Pyrazole H), 7.15–7.50 (m, 9H, Ar-H), 14.4 (br, 1H, NH ex-
changeable)
3.8 (s, 3H, –OCH3), 7.13 (s, 1H, Pyrazole H), 7.2–7.6 (m, 9H, Ar-H), 14.5
(br, 1H, NH exchangeable)
evaluation of the tested compounds are listed in (Table 2) Their activities are comparable to that of amantadine,
and are illustrated by (Figs. 1 and 2). The physical data of especially at a concentration of 20 lg/mL, while oxadia-
compounds 3–14 are listed in Table 3.
zolethione 9b showed the highest activity towards HSV-1
The results presented in Table 2 and Figs. 1 and 2 compared to that of the other compounds tested, which
reveal that oxadiazole 6b, thiosemicarbazide 7b, and oxa- show moderate activities especially at the aforemen-
diazolethione 9a show the highest activities towards the tioned concentration.
HAV virus compared with the other tested compounds.
i 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim