Synthesis and antitumor activity evaluation of some N-heterocycles derived from pyrazolyl-substituted 2(3H)-furanone

ABSTRACT

Pyrazolyl-substituted 2(3H)-furanone was allowed to react with different nitrogen nucleophiles such as hydrazine hydrate, ethylenediamine, ethanolamine, and anthranilic acid to give pyrrolone and benzoxazinone derivatives. The acid hydrazide 3 was reacted with some carbonyl compounds such as 4-chlorobenzaldehyde, chloroacetyl chloride, and acetic anhydride to give thiazolidinone, oxadiazole, and pyridazinone derivatives. Selected examples of the synthesized compounds were evaluated as anticancer agents against three types of carcinoma cell lines (HePG 2, HCT116, and PC3), using Doxorubicin as a reference drug. The result revealed that some of the new compounds showed high activities. Compound 6a was more potent than the standard drug. A docking study using MOE 2008.10 program was performed.

GRAPHICAL ABSTRACT

KEYWORDS:

• Antitumor activities
• 2(3H)-furanone
• pyrazole
• pyrrolones
• thiazolidinones