Abstract
On the basis of our consideration to design and to develop antitumor activities of heterocyclic compound derivatives, especially in fused ring system, we refer to the possibility of the heterocyclic extension of one of the most important steroid compounds used as a medicinal drug. The reaction of dydrogesterone with each of the malononitrile or ethylcyanoacetate containing elemental sulfur afforded thiophene derivatives
. Also, dydrogesterone was reacted with a mixture of ethylcyanoacetate–hydrazine, ethylcyanoacetae–urea, or ethylcyanoacetate–thiourea to produce pyrazole derivative
and pyrimidine derivatives
. Thienopyrimidine derivatives
were introduced from the reaction of thiophene derivatives
with either phenylisothiocyanate or benzoylisothioyanate. Furthermore, compounds
were directed toward the reaction with ethylcyanoacetate to produce compounds
, and the last compounds
were directed toward cyclization to obtain thienopyridine derivatives
. In addition, compounds
were subjected to react with different carbonyl compounds, such as salicylaldehyde, cyclopentanone-elemental sulfur, malonaldehyde, and acetylacetone to produce coumarin derivatives
, fused thiophene derivatives
, and pyridine derivatives
. Isooxazole derivatives
were afforded through the reaction of compounds
with hydroxylamine hydrochloride. Finally, 2-pyridone derivatives
were obtained through the reaction of compounds
with benzoylacetonitrile. Conformation structure of the synthesized compounds was established by applying IR,
H NMR,
C NMR, and mass spectrometry, and their antitumor activity was examined. Some compounds showed promising growth inhibitory effects on the three different cell lines.