Abstract
Pyrazoles, thiazoles and fused thiazoles have been reported to possess many biological activities. 3-Methyl-5-oxo-4-(2-arylhydrazono)-4,5-dihydro-1
H
-pyrazole-1-carbothioamides
3a
,
b
(obtained from the reaction of ethyl 3-oxo-2-(2-arylhydrazono)butanoates
1a
,
b
with thiosemicarbazide) could be transformed into a variety of thiazolyl-pyrazole derivatives
6a
–
h
,
10a
–
c
,
15a
–
c
,
17
,
19
and
21
via their reaction with a diversity hydrazonoyl chlorides as well as bromoacetyl derivatives. Moreover, the computational studies were carried out for all new compounds. The results indicated that five compounds showed promising binding affinities
(10a
: − 3.4 kcal/mol,
6d
: − 3.0 kcal/mol,
15a
: − 2.2 kcal/mol,
3a
: − 1.6 kcal/mol, and
21
: − 1.3 kcal/mol) against the active site of the epidermal growth factor receptor kinase (EGFR). The cytotoxicity of the potent products
3a
,
6d
,
10a
,
15a
, and
21
was examined against human liver carcinoma cell line (HepG-2) and revealed activities close to Doxorubicin standard drug. There was an understanding between the benefits of restricting affinities and the data obtained from the practical anticancer screening of the tested compounds.