Cholyl 1,3,4-oxadiazole hybrid compounds: design, synthesis and antimicrobial assessment

Rasras, Anas J.; El‐Naggar, Mohamed; Safwat, Nesreen A.; Al‐Qawasmeh, Raed A.

doi:10.3762/bjoc.18.63

Cited by 9 publications

(9 citation statements)

References 33 publications

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“…Our synthetic strategy commenced from the commercially available adamantane carboxylic acid (1), as in scheme 1, then synthesis of adamantanyl hydrazide (3) as previously reported [26,27]. Subsequently, re uxing adamantanyl hydrazide (3) with carbon disul de and trimethylamine in ethanol yielded 1,3,4oxadiazole-2-thiol (4) with good yield (85%) [39,40]. The thiol of 4 was then reacted with propargyl bromide (3-Bromoprop-1-yne) and sodium carbonate (Na 2 CO 3 ) in acetonitrile to afford the thiopropargylated derivative (5) in 75% yield after 12 h [39].…”

Section: Chemistrymentioning

confidence: 99%

“…Subsequently, re uxing adamantanyl hydrazide (3) with carbon disul de and trimethylamine in ethanol yielded 1,3,4oxadiazole-2-thiol (4) with good yield (85%) [39,40]. The thiol of 4 was then reacted with propargyl bromide (3-Bromoprop-1-yne) and sodium carbonate (Na 2 CO 3 ) in acetonitrile to afford the thiopropargylated derivative (5) in 75% yield after 12 h [39]. Compound (5) was used as starting point for Mannich reaction to generate a library of 16 diverse compounds (6a-p) shown in Table 1.…”

Section: Chemistrymentioning

confidence: 99%

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Synthesis, anticancer evaluation and docking studies of novel adamantanyl-1,3,4-oxadiazol hybrid compounds as Aurora-A kinase inhibitors

Jaber

Al-Mahadeen

Al‐Qawasmeh

et al. 2023

Preprint

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Cancer is a devastating disease, but advancements in cancer treatment offer hope for the future. Aurora Kinases are a family of serine/threonine kinases that play critical roles in cell cycle control and mitosis. There are three members of the Aurora kinase family in humans: Aurora-A kinase, Aurora-B kinase, and Aurora-C kinase. This study focuses on the synthesis of hybrid compounds combining adamantane and 1,3,4-oxadiazole as potential inhibitors of Aurora-A kinase. A series of novel 4-((5-((3r,5r,7r)-adamantan-1-yl)-1,3,4-oxadiazol-2-yl)thio)-N,N-2-yn-1-amine were synthesized and evaluated against Aurora-A kinase. The most potent derivatives were 6a and 6k with IC50 values 36.6 and 38.8 μM, respectively. Docking studies probed the binding interactions of these compounds within the active site of the kinase. The findings contribute to the development of novel cancer therapeutics and offer promise for more effective and targeted treatments in the future.

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Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Synthesis, anticancer evaluation and docking studies of novel adamantanyl-1,3,4-oxadiazol hybrid compounds as Aurora-A kinase inhibitors

Jaber

Al-Mahadeen

Al‐Qawasmeh

et al. 2023

Preprint

Self Cite

View full text Add to dashboard Cite

show abstract

Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Synthesis, anticancer evaluation and docking studies of novel adamantanyl-1,3,4-oxadiazol hybrid compounds as Aurora-A kinase inhibitors

Jaber,

Al-Mahadeen,

Al-Qawasmeh

et al. 2023

Med Chem Res

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Cancer is a devastating disease, but advancements in cancer treatment offer hope for the future. Aurora Kinases are a family of serine/threonine kinases that play critical roles in cell cycle control and mitosis. There are three members of the Aurora kinase family in humans: Aurora-A kinase, Aurora-B kinase, and Aurora-C kinase. This study focuses on the synthesis of hybrid compounds combining adamantane and 1,3,4-oxadiazole as potential inhibitors of Aurora-A kinase. A series of novel 4- ((5-((3r,5r,7r)-adamantan-1yl)-1,3,4-oxadiazol-2-yl)thio)-N,N-2-yn-1-amine were synthesized and evaluated against Aurora-A kinase.The most potent derivatives were 6a and 6k with IC 50 values 36.6 and 38.8 μM, respectively. Docking studies probed the binding interactions of these compounds within the active site of the kinase. The ndings contribute to the development of novel cancer therapeutics and offer promise for more effective and targeted treatments in the future.

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“…The molecular structure of a compound profoundly influences its biological activity, and herein lies the allure of heterocyclic compounds, many of which feature the inclusion of sulfur [6][7] and nitrogen [8][9][10] atoms. Such compounds bear the potential to wield substantial pharmaceutical activity and manifest in diverse medical applications, thus underscoring their significance and multifaceted nature [11]. Extensive studies have elucidated the therapeutic effects of compounds harboring the 1,3,4-thiadiazole ring [12][13], shedding light on their prowess in combating a myriad of pathological states encompassing antibacterial, antimycotic, antitubercular, anti-Parkinson, cancer-fighting, anti-inflammatory, and anticonvulsant activities.…”

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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Cholyl 1,3,4-oxadiazole hybrid compounds: design, synthesis and antimicrobial assessment

Cited by 9 publications

References 33 publications

Synthesis, anticancer evaluation and docking studies of novel adamantanyl-1,3,4-oxadiazol hybrid compounds as Aurora-A kinase inhibitors

Synthesis, anticancer evaluation and docking studies of novel adamantanyl-1,3,4-oxadiazol hybrid compounds as Aurora-A kinase inhibitors

Synthesis, anticancer evaluation and docking studies of novel adamantanyl-1,3,4-oxadiazol hybrid compounds as Aurora-A kinase inhibitors

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

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