Synthesis and biological evaluation of new series of phthalazinone, pyridazinone, oxadiazole, pyrazolone scaffolds based on coumarin-3-carbohydrazide

Document Type : Original Research Papers

Authors

Chemistry Dept., Faculty of Science, Benha University, Benha, Egypt

Abstract

A new series of  phthalazinone, pyridazinone, oxadiazole, pyrazolone scaffolds based on coumarin-3-carbohydrazide was efficiently synthesized. Reaction of hydrazine hydrate with 2-oxo-2H-chromene carboxylate (1) produced the key compound coumarin-3-carbohydrazide (2), which used for synthesizingSchiff’s base derivatives (3a-d). 
The hydrazide (2) was used for efficient synthesis of different scaffolds such as dihydrophthalazine-1,4-Dione (4a, 4b), pyridazinone derivatives (5) and (6) via treatment with phthalic anhydride and/or tetrabromo phthalic anhydride, maleic anhydride and succinic anhydride, respectively. Moreover,Reaction of benzoic acid and/or acetic acid with coumarin-3-carbohydrazide (2) in phosphorous oxychloride produced the oxadiazole derivatives (8a, b). 
Pyrazolone and pyrazolidinone scaffolds (9-12) wereobtained in good yields upon reaction of the hydrazide derivative (2) with numerous active methylene compounds such as acetylacetone, ethyl cyanoacetate, ethyl acetoacetate, and diethyl malonate.
Evaluation of antimicrobial activity of some of the synthesized compounds towards the selected bacteria and fungi strains in comparison with Gentamicin and ketoconazole as reference drugs revealed that compounds 3d, 6, 8a, 8b, 11, 12 and 14 exhibited promising activity in comparison to the tested standard.
The products structures were assigned and confirmed via their elemental analyses as well as spectral data (IR, MS and 1H NMR).

Keywords

Benha Journal of Applied Sciences
Volume 7, Issue 2
February 2022
Pages 21-29

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