Abstract
A novel series of 1,2,3-triazole containing sulfonamide moiety was synthesized. Treatment of 4-acetyl 1,2,3-triazole
3
with different aldehydes gave
α
,
β
-unsaturated ketones
4a
–
c
. Condensation of
3
with dimethylformamide dimethylacetal (DMF-DMA) gave formimidamide
5
. Chalcone
7
was achieved via two ways from the reaction of
5
with benzaldehyde or from treatment of
4a
with DMF-DMA. Reaction of
7
with hydrazine hydrate afforded pyrazoline
8
. 5-Methyl pyrazole
12
was synthesized from Claisen condensation reaction of
3
or
5
with ethyl acetate to give 1,3-diketone adduct
9
or
10
, respectively, followed by treatment with hydrazine hydrate. 5-Aminopyrazole
17
was synthesized from the reaction of ester
13
or formimidamide ester
13a
with acetonitrile to afford cyanoacetyl derivatives
14
or
15
, respectively, followed by treatment with hydrazine hydrate. The new compounds were screened for their in vitro antitumor activity. The results of this investigation revealed that compounds
12
,
7
, and
17
had a significant anticancer activity against MCF-7 cancer cell line with IC
50
values 12.4, 19.8, and 23.4 µM, respectively, in relation to the standard drug, doxorubicin.