Med Chem Res (2012) 21:3390–3395
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Table 2 4,5-diaryl-2-[4-(t-amino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-ones (10–25)
( C H 2 )
N
N
N
A r 1
O
N
A r 2
Compound
number
%
Melting
Elemental analyses
Yield point °C
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
20.8 116–118
4,5-Di-phenyl-2-[4-(2,6-dimethylpiperidine)-2-butnyl]-2,4-dihydro-3H-1,2,4-triazol-3-one, Anal. Calcd.
for C25H28N4O; C 74.96, H 7.04, N 13.93, Found C 74.92, H 7.06, N 13.94.
43.12 68–70
4,5-Di-phenyl-2-[4-(perhydroazepino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one, Anal. Calcd. for
C
24H26N4O; C 74.58, H 6.78, N 14.49, Found C 74.54, H 6.74, N 14.47.
4,5-Di-pheny1-2-[4-(perhydroazocino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one, Anal. Calcd. for
25H28N4O; C 74.96, H 7.04, N 13.98, Found C 74.94, H 7.02, N 13.99.
4,5-Di-phenyl-2-[4-(2-methylpiperidino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one, Anal. calcd. for
24H26N4O; C 74.58, H 6.78, N 14.49, Found C 74.59, H 6.76, N 14.47
4,5-Di-phenyl-2-[4-(3-methylpiperidino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one, Anal. Calcd. for
24H26N4O; C 74.58, H 6.78, N 14.49, Found C 74.56, H 6.74, N 14.46.
4,5-Di-phenyl-2-[4-(pyrrolidino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one, Anal. Calcd. for
22H22N4O; C 73.71, H 6.18, N 15.63, Found C 73.68, H 6.19, N 15.60.
4,5-Di-phenyl-2-[4-(pyrrolidino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one, Anal. Calcd. for
23H24N4O; C 74.16, H 6.49, N 15.04, Found C 74.15, H 6.45, N 15.05.
50.55 84–85
C
80.812 90–92
C
51.74 100–102
41.85 98–100
56.53 117–119
61.036 110–112
93.58 100–101
26.73 132–134
24.96 99–100
33.216 118–120
49.91 138–140
27.86 107–109
19.19 137–139
20.53 138–140
C
C
C
4-(1-Naphthyl)-5-phenyl-2-[4-(2,6-dimethylpiperidino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one,
Anal. Calcd. for C29H30N4O; C 77.30, H 6.71, N 12.43, Found C 77.32, H 6.70, N 12.42.
4-(1-Naphthyl)-5-phenyl-2-[4-(piperidino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one, Anal. Calcd.
for C27H26N4O.0.5H2O; C 75.14, H 6.30, N 12.98,Found C 75.18, H 6.32, N 13.00.
4-(1-Naphthyl)-5-phenyl-2-[4-(2-methylpiperidino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one, Anal.
Calcd. for C28H28N4O. 0.5H2O; C 75.47, H 6.56, N 12.57, Found C 75.50, H 6.54, N 12.59.
4-(1-Naphthyl)-5-phenyl-2-[4-(3-methylpiperidino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one,
Anal.Calcd. for C28H28N4O. 0.5H2O; C 75.47, H 6.56, N 12.57, Found C 75.50, H 6.53, N 12.60.
4-(1-Naphthyl)-5-phenyl-2-[4-(perhydroazepino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-
one,Anal.Calcd. for C28H28N4O; C 77.03, H 6.46, N 12.83, Found C 77.00, H 6.49, N 12.81.
4-(1-Naphthyl)-5-phenyl-2-[4-(perhydroazecino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one,
Anal.Calcd. for C29H30N4O; C 77.30, H 6.71, N 12.43, Found C 77.26, H 6.72, N 12.41.
4-Phenyl-5-(p-chlorophenyl)-2,[4-(2,6-dimethylpiperidino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-
one, Anal. Calcd. for C25H27CLN4O. H2O; C 66.28, H 6.45, N 12.36, Found C 66.24, H 6.42, N 12.38.
4-Phenyl-5-(p-chlorophenyl)-2,[4-(2-methylpiperidino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one,
Anal. Calcd. for C24H25CLN4O. H2O; C 65.67, H 6.20, N 12.76, Found C 65.63, H 6.19, N 12.78.
4-Phenyl-5-(p-chlorophenyl)-2,[4-(piperidino)-2-butynyl]-2,4-dihydro-3H-1,2,4-triazol-3-one, Anal.
Calcd. for C23H23CLN4O. H2O; C 65.16, H 5.94, N 13.21, Found C 65.18, H 5.92, N 13.24.
concentration that yield turbidity less than or equal to that
for 80% inhibition compared with the growth in the growth
control well.
Cyclization of 1-aroyl-4-aryl-semicarbazides (1–3) in
aqueous potassium hydroxide generated the 4,5-diaryl-2,4-
dihydro-3H-1,2,4-triazol-3-ones (4–6). Treatment of the
ethanolic solution of (4–6) with propargyl bromide at 60°C
afforded the 4,5-diaryl-2-(2-propynyl)-2,4-dihydro-3H-
1,2,4-triazol-3-ones (7–9). The Mannich reaction of (7–9)
with paraformaldehyde and the appropriate cyclic amines in
the presence of catalytic amount of cuprous chloride, yiel-
ded the 4,5-diaryl-2-(4-tert-amino)-2-butynyl)-2,4-dihydro-
3H-1,2,4-triazol-3-ones (10–25). The new compounds were
tested for antibacterial and antifungal activity according to
MIC breakpoints for defining susceptibility were in
accordance with the description by National Committee for
Clinical laboratory Standards (NCCLS 1998).
Results and discussion
The designed compounds were prepared according to
Scheme 1.
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