Sythesis of Some New Quinazolin-4-one Derivatives

doi:10.21608/ejchem.2011.1402

Cited by 3 publications

(1 citation statement)

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“…Moreover, ve membered nitrogen heterocycles are vital targets that exploited in the design of antibacterial drug candidates. [12][13][14][15][16] According to the recent studies, quinazolin-2,4-dione fragment attached to acylthiourea core and/or ve membered nitrogen heterocycles possess biological activity, 17 including anticancer, 18 anti-malarial, 19 antibacterial, 20 antiviral, 21 antifungal 22 and anti-inammatory. 23 Our targeted molecules structure design has created from marketed available drugs.…”

Section: Introductionmentioning

confidence: 99%

New quinazolin-2,4-dione derivatives incorporating acylthiourea, pyrazole and/or oxazole moieties as antibacterial agents via DNA gyrase inhibition

Ibrahim,

Hassan,

Mosallam

et al. 2024

RSC Adv.

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Section: Introductionmentioning

confidence: 99%

New quinazolin-2,4-dione derivatives incorporating acylthiourea, pyrazole and/or oxazole moieties as antibacterial agents via DNA gyrase inhibition

Ibrahim,

Hassan,

Mosallam

et al. 2024

RSC Adv.

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Ultrasonic Aptitude of Regioselective Reaction of 6‐bromo‐spiro‐3,1‐benzoxazinone2,1′‐isobenzofuran‐3′,4‐dione Towards Some Electrophilic and Nucleophilic Reagents

El‐Hashash

Rizk

El‐Badawy

2018

Journal of Heterocyclic Chem

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In the present work, the 2‐benzoxazinonyl benzoic acid (BBA) could be isomerized to the stereogenic spiro products (SBI) via ultrasonic and basic reaction conditions. The spiro compounds (SBI) have both electrophilic and nucleophilic centers. A series of nitrogen nucleophiles such as hydrazine hydrate, glycine, 2‐aminopyridine, 2‐picolinylamine, 4‐anisidine, 4‐aminoacetophenone and carbon electrophiles such as oxiranylmethylchloride, ethylchloroacetate, chloroacetylchloride, Mannich reagents, for example, formaldehyde with piperidine or morpholine can be treated with 2‐benzoxazine‐2‐yl benzoic acid (BBA) via multicomponent reaction. The basicity of previous nucleophiles can be controlled on the course of reaction of 2‐benzoxazinonyl benzoic acid. The chemical structure of the synthesized compounds can be confirmed by microanalytical, spectral data and optimized by quantum chemical parameters.

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Facile Synthesis, Characterization, and Antimicrobial Evaluation of Novel Heterocycles, Schiff Bases, and <i>N</i>-Nucleosides Bearing Phthalazine Moiety

2016

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The present work describes convenient synthesis of the novel Schiff bases 5a and b by reacting phthalazinones 4a and b with 4-methoxybenzaldehyde Reaction of the Schiff bases with phenylisothiocyanate afforded diazetidine derivatives 7a and b. Also, compounds 4a and b reacted with 2-bromoglucoside tetraacetate giving peracetylated N-glycosides 6a and b, which were deacetylated to afford N-glycosylated phthalazinones 8a and b. On the other hand, when compound 3 was treated with POCl 3 /PCl 5 and/or ethyl chloroacetate, chlorophthalazine and ethyl acetate derivatives 9 and 10 were obtained, respectively. Hydrazinolysis of compounds 9 and 10 produced the hydrazino and hydrazide derivatives 11 and 12, respectively. When compound 11 reacted with 2-furanaldehyde, acetic anhydride, and/or carbon disulphide, it gave compounds 13-15, respectively. Treatment of the hydrazide 12 with aromatic aldehydes, acetic anhydride, ethyl acetoacetate, acetyl acetone, ammonium thiocyanate, and/or phthalic anhydride furnished compounds 17-21. Meanwhile, reacting Schiff base 22 with the chlorophthalazine derivative 9 produced compound 23, which on treatment with furoyl chloride produced compound 24. The structures of the novel compounds were confirmed by IR, 1 H-NMR, 13 C-NMR, MS, and elemental analysis. The newly synthesized compounds were tested against Bacillus subtilis and Staphylococcus aureus as Gram-positive bacteria, Escherichia coli and Pseudomonas aurignosa as Gram-negative bacteria, and Candida albicans and Aspergillus niger as fungi strains. Compounds 5a and b, 23, and 24 showed greater antimicrobial activity than the stranded compounds, suggesting that they could be considered as promising antimicrobial agents.Key words phthalazin-1-one; N-glycosylated phthalazinone; Schiff base; diazetedine; antimicrobial activity Phthalazines as N-heterocycles have received considerable attention in the literature as a consequence of their role as pharmacophore.1,2) Recently, they are derived from a wide range of biologically active natural products, troponoid family.3) A novel series of N-substituted-4-phenyl/benzylphthalazin-1-ones, phthalzine-1,4-dione showed antitumor activity. were prepared from the corresponding phthalazinones. Moreover, many substituted and fused phthalazine and phthalzinone derivatives exhibited antimicrobial activity. 23-26)On the basis of the above findings and in continuation of our research interest in the synthesis of novel biologically active heterocycles, [27][28][29][30][31] and with the aim of preparing new derivatives of phthalazine with potential pharmacological activity, we report here the synthesis of novel Schiff bases containing phthalazine moiety, phthalazinone and fused phthalazine derivatives, followed by evaluation of their antimicrobial activity against different strains of bacteria and fungi, where most of synthesized compounds exhibited a moderate to a strong antimicrobial activities. Some of the tested compounds showed antimicrobial activity higher than the reference compounds. Results and D...

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Sythesis of Some New Quinazolin-4-one Derivatives

Cited by 3 publications

References 7 publications

New quinazolin-2,4-dione derivatives incorporating acylthiourea, pyrazole and/or oxazole moieties as antibacterial agents via DNA gyrase inhibition

New quinazolin-2,4-dione derivatives incorporating acylthiourea, pyrazole and/or oxazole moieties as antibacterial agents via DNA gyrase inhibition

Ultrasonic Aptitude of Regioselective Reaction of 6‐bromo‐spiro‐3,1‐benzoxazinone2,1′‐isobenzofuran‐3′,4‐dione Towards Some Electrophilic and Nucleophilic Reagents

Facile Synthesis, Characterization, and Antimicrobial Evaluation of Novel Heterocycles, Schiff Bases, and <i>N</i>-Nucleosides Bearing Phthalazine Moiety

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