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223811

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

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Last updated: 05 Jan 2025

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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).

DOI

10.21608/bjas.2022.223811

Keywords

Coumarin-3-carbohydrazide, Scaffolds, Oxadiazole, pyrazolone, phthalazine, pyridazine, antimicrobial activity

Authors

First Name

A.A.

Last Name

Aly

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Affiliation

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

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Orcid

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First Name

M.A.

Last Name

Abo-Riya

MiddleName

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Affiliation

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

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Orcid

-

First Name

A.A.

Last Name

El-Shiekh

MiddleName

-

Affiliation

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

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City

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Orcid

-

First Name

Aya.

Last Name

I.Elkala

MiddleName

-

Affiliation

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

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Volume

7

Article Issue

2

Related Issue

31999

Issue Date

2022-02-01

Receive Date

2022-02-09

Publish Date

2022-02-01

Page Start

21

Page End

29

Print ISSN

2356-9751

Online ISSN

2356-976X

Link

https://bjas.journals.ekb.eg/article_223811.html

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https://bjas.journals.ekb.eg/service?article_code=223811

Order

3

Type

Original Research Papers

Type Code

1,647

Publication Type

Journal

Publication Title

Benha Journal of Applied Sciences

Publication Link

https://bjas.journals.ekb.eg/

MainTitle

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

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Article

Created At

23 Jan 2023