Synthesis, Characterization of some New 1, 3, 4-Oxadiazole derivatives based on 4- amino benzoic acid

Al-Zobaydi, Shatha F.; Karim, Bushra; Al-Sahib, Sanaa A.; Ismael, Ban Dha.

doi:10.21123/bsj.2016.13.2.2ncc.0289

Cited by 2 publications

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“…Tetrazole synthesis requires the cyclization of thiosemicarbazide under strong initial conditions. Furthermore, oxadiazole and β-lactam can be synthesized via different literature methods [26][27][28][29][30][31].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of some new heterocyclic derivatives from aromatic carbonyl ‎compounds and carboxylic acids with Evaluation some of them for biological activity

Al-Khazraji,

Ahamed,

Ali

2024

Iraqi Journal of Science

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In this research investigation, a total of eighteen diverse tetra- and penta-lateral cyclic compounds were synthesized. These included 1,3,4-thiadiazole, thiazolidin-4-one (via an alternative method), 1,2,4-triazole, carbothioamide, thiazole-4-one, azetidin-2-one, and oxazole. The synthesis procedure entailed a sequence of reactions. The thiazolidine-4-one 1 was obtained by reaction p-aminobenzoic acid with thiosemicarbazide, followed by treatment with p-tolualdehyde to produce Schiff base 2. Reaction Schiff base 2 with mercaptoacetic acid in dry benzene was carried out to produce thiazolidine-4-one 3. In another synthesis pathway, the esterification of p-nitro benzoic acid with ethanol in the presence of sulfuric acid was obtained to formation of compound 4. Compound 4 was subsequently reacted with thiosemicarbazide, yielding compound 5. Cyclization of compound 5 was then achieved using 4% sodium hydroxide solution. This formed the 1,2,4-triazole heterocycle, designated compound 6. Thiosemicarbazone 7-9 were prepared by reaction of thiosemicarbazide with different aldehydes. Additionally, 2-substituted-1,3-thiazolidine-4-one derivatives 10-12 were synthesized through the reaction of thiosemicarbazone with chloroacetic acid in the presence of anhydrous sodium acetate. The Oxazole derivative 15 was obtained through a series of reactions starting with the reaction of p-amino benzoic acid with ethyl chloroacetate, resulting in compound 13. Compound 13 was then treated with urea to obtain compound 14, followed by a reaction with 4-phenyl phenacyl bromide to yield the final product, the Oxazole derivative 15. The 2-aminooxadiazole derivative 16 was synthesized by reaction urea with 4-bromoacetophenone which was reacted with 4-bromobenzaldehyde to produce Schiff base derivative 17. Finally, β-lactam 18 is obtained through reaction Schiff base with chloroacetyl chloride in the presence of triethyl amine. FT-IR, 1H-NMR, and 13C-NMR spectroscopy were used to confirm their proposed structures. Moreover, the antibacterial and antifungal activities of certain synthesized compounds, specifically 2,3,6,11,13,15,17, and 18, were assessed against Staphylococcus aureus, Escherichia coli, and Candida albicans, demonstrating encouraging outcomes.Keywords: Antibacterial, antifungal activity, oxadaizole, heterocyclic derivatives, Oxazole.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of some new heterocyclic derivatives from aromatic carbonyl ‎compounds and carboxylic acids with Evaluation some of them for biological activity

Al-Khazraji,

Ahamed,

Ali

2024

Iraqi Journal of Science

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“…It is also an important pharmacophore of top selling harmaceutical drugs such as, Azelastine, Ameziniummetalilsulfate, Emorfazone, Cadralazine, Hydralazine, Minaprine and Sulfamethoxypyridazine. Pyridazine molecule and its derivatives are also known to possess a wide range of biological activities, such as anticancer, antiviral, antituberculosis, antidepressant, analgesic, antimicrobial and in platelet aggregation (21)(22)(23)(24)(25). The aim of the reasearch is the synthesis and characterization of organic compounds and study the effect of compounds on cancer cell line (Hep-2).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization of Poly Heterocyclic Compounds, and Effect on Cancer Cell (Hep-2) In vitro.

Journal¹

2018

Baghdad Sci.J

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A synthesis series of new heterocyclic derivatives (A2-A7) (pyrrole, pyridazine, oxazine and imidazol) derived from 4-acetyl-2,5-dichloro-1-(3,5-dinitrophenyl)-1H-pyrrole-3-carboxylate(A1) have been synthesised. Synthesis of compound (A2) by the reaction of starting material (A1) with hydroxyl amine hydrochloride in the presence of pyridine. Compound (A2) was reacted with hydrazine hydrate in dry benzene to give (A3) derivative. The compound )A3( deals with sodium nitrite to give diazonium salt, and the reaction diazonium salt with ethyl acetoacetate to produce compound (A4). To a mixture of compound (A4) and hydroxyl amine with sttired to yield (A5).Compound (A6) was prepared by reaction compound (A4) with thiosemicarbazide in presence of drops of acetic acid. Synthesis of 1compound (A7) by reaction compound (A6) with ethyl chloro acetate. The reactions have been monitored by TLC and the synthesized compounds were characterized using spectrophotometric methods FT-IR, 1H NMR.The biological effects of the prepared compounds on the cancer cells were studied in vitro. The results indicated that these Synthesized compounds (A1–A7) inhibited1 the cancer1 cells1 efficiently, the compound (A6) was activity inhibited on the cancer cells.

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Synthesis, Characterization of some New 1, 3, 4-Oxadiazole derivatives based on 4- amino benzoic acid

Cited by 2 publications

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Synthesis and Characterization of some new heterocyclic derivatives from aromatic carbonyl ‎compounds and carboxylic acids with Evaluation some of them for biological activity

Synthesis and Characterization of some new heterocyclic derivatives from aromatic carbonyl ‎compounds and carboxylic acids with Evaluation some of them for biological activity

Synthesis, Characterization of Poly Heterocyclic Compounds, and Effect on Cancer Cell (Hep-2) In vitro.

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