Synthesis and antibacterial activity of N,N′-diaryl-2-aryl-6-hydroxy-6-methyl-4-oxocyclohexane-1,3-dicarboxamides

Гейн, В. Л.; Levandovskaya, E. V.; Nosova, N. V.; Antonova, N. V.; Воронина, Э. В.; Вахрин, М. И.; Кривенько, А. П.

doi:10.1007/s11094-008-0043-8

Cited by 17 publications

(7 citation statements)

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“…The reaction of β-oxoanilide 1 with the chalcone derivative 19 in ethanolic piperidine solution under reflux afforded a reaction product that could be formulated as the cyclized benzene derivative 21 as literature [17] or the pyridine derivative 22. The structure 21 was ruled out according to the un-identical spectroscopic data for the structure.…”

Section: Resultsmentioning

confidence: 99%

<i>β</i>-Oxoanilides in Heterocyclic Synthesis: Synthesis and Antimicrobial Activity of Pyridines, Pyrans, Pyrimidines and Azolo, Azinopyrimidines Incorporating Antipyrine Moiety

Hussein¹,

Gad‐Elkareem²,

El-Adasy³

et al. 2012

IJOC

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Condensation of β-Oxoanilide 1 with active methylene derivatives 2a,b afforded the pyridine derivative 5, and with crotononitrile afforded the pyridine 8. Compounds 9 and 11a-c were obtained by reaction of 1 with malononitrile dimer and arylidinemalononitrile 10a-10c. In contrast, when compound 1 reacted with ethoxymethylen malononitrile afforded the pyridine derivative 13. On the other hand, treatment of 1 with anthranilic acid gave the quinoline derivative 14. Also, reactions of 1 with isothiocyanate derivatives afforded compounds 16-18. The reaction of 1 with chalcone derivative afforded the pyridine derivative 22. Treatment of compound 1 with thiourea produced pyrimidine derivative 23. Furthermore, compound 1 converted into pyrimidinethione 24a and pyrimidinone 24b on treatment with a mixture of aromatic aldehydes and thiourea or urea respectively. Reaction of 24a with hydrazonyl halide, thiosemicarbazide and arylidinecyanothioacetamide afforded compounds 26, 28 and 29. Compound 29 was treated with chloroacetonitrile to afford compound 30. Six compounds from the newly synthesized were screened for antibacterial and antifungal activity against bacteria Staphylococcus aureus, Bacillus cereus and Klebsiella pneumonia and fungi Aspergillus flavus and Aspergillus ochraceous, respectively. Some of the tested compounds showed significant antimicrobial activity. IR, 1 H NMR, mass spectral data, and elemental analysis elucidated the structures of all the newly synthesized compounds.

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Section: Resultsmentioning

confidence: 99%

<i>β</i>-Oxoanilides in Heterocyclic Synthesis: Synthesis and Antimicrobial Activity of Pyridines, Pyrans, Pyrimidines and Azolo, Azinopyrimidines Incorporating Antipyrine Moiety

Hussein¹,

Gad‐Elkareem²,

El-Adasy³

et al. 2012

IJOC

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“…Functionalized cyclohexanones are embedded in the antidepressant and dissociative anesthetic drugs Ketanest ® S [11] and Vasoxyl ® methoxamine (for the treatment of hypotension) [12]. These molecules possess antibacterial [13], anticonvulsant [14], antifungal and anticancer [15] properties. In general, cyclohexanone is a common scaffold in various bioactive heterocycles of medicinal interests, particularly those used for the treatment of asthma and central nervous system (CNS)- and chronic obstructive pulmonary diseases (COPD)-related diseases, due to its inhibitory activity against phosphodiesterase 4 (PDE4) [16,17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Pyridine-Dicarboxamide-Cyclohexanone Derivatives: Anticancer and α-Glucosidase Inhibitory Activities and In Silico Study

et al. 2019

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An efficient and practical method for the synthesis of 2,6-diaryl-4-oxo-N,N′-di(pyridin-2-yl)cyclohexane-1,1-dicarboxamide is described in this present study, which occurs through a double Michael addition reaction between diamide and various dibenzalacetones. The reaction was carried out in dichloromethane (DCM) in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The anticancer activities of the synthesized compounds were evaluated in several cancer cell lines, including MCF-7, MDA-MB-231, SAS, PC-3, HCT-116, HuH-7 and HepG2 cells. From these experiments, we determined that MDA-MB-231 was the most sensitive cancer cell line to the compounds 3c, 3e, 3d, 3j and 3l, which exhibited variable anticancer activities (3l [IC50 = 5 ± 0.25 µM] > 3e [IC50 = 5 ± 0.5 µM] > 3c [IC50 = 7 ± 1.12 µM] > 3d [IC50 = 18 ± 0.87 µM] > 3j [IC50 = 45 ± 3 µM]). Of these, 3l (substituted p-trifluoromethylphenyl and chloropyridine) showed good potency (IC50 = 6 ± 0.78 µM) against HCT-116 colorectal cancer cells and exhibited high toxicity against HuH-7 liver cancer cells (IC50 = 4.5 ± 0.3 µM). These values were three times higher than the values reported for cisplatin (IC50 of 8 ± 0.76 and 14.7 ± 0.5 µM against HCT-116 and HuH-7 cells, respectively). The highest α-glucosidase inhibitory activity was detected for the 3d, 3i and 3j compounds. The details of the binding mode of the active compounds were clarified by molecular docking studies.

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“…Previously, we have obtained new oxocyclohexane-1,3-dicarboxamide derivatives by the condensation of acetoacetic acid amides with aromatic aldehydes in the presence of a basic piperidine catalyst in ethanol at room temperature [28][29][30][31]. The reactions of the obtained compounds with N-nucleophiles [29] and Baeyer-Villiger oxidation [33] have been studied.…”

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confidence: 99%

“…In continuation of studying the reactivity of cyclohexanone derivatives [28][29][30][31][32][33][34] and in order to obtain new compounds with potential biological activity, herein we reported the reactions of N 1 ,N 3 ,2-triaryl-6-hydroxy-6-methyl-4-oxocyclohexane-1,3-dicarboxamides with acid hydrazides and thiosemicarbazide. New derivatives SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF NOVEL HYDRAZONE of hydrazones and 1,2,4-triazole-3-thione were obtained, respectively.…”

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confidence: 99%

Synthesis and Antimicrobial Activity of Novel Hydrazone and 1,2,4-Triazole-3-thione Derivatives

et al. 2022

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Synthesis and antibacterial activity of N,N′-diaryl-2-aryl-6-hydroxy-6-methyl-4-oxocyclohexane-1,3-dicarboxamides

Cited by 17 publications

References 2 publications

<i>β</i>-Oxoanilides in Heterocyclic Synthesis: Synthesis and Antimicrobial Activity of Pyridines, Pyrans, Pyrimidines and Azolo, Azinopyrimidines Incorporating Antipyrine Moiety

<i>β</i>-Oxoanilides in Heterocyclic Synthesis: Synthesis and Antimicrobial Activity of Pyridines, Pyrans, Pyrimidines and Azolo, Azinopyrimidines Incorporating Antipyrine Moiety

Synthesis of Pyridine-Dicarboxamide-Cyclohexanone Derivatives: Anticancer and α-Glucosidase Inhibitory Activities and In Silico Study

Synthesis and Antimicrobial Activity of Novel Hydrazone and 1,2,4-Triazole-3-thione Derivatives

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Synthesis and antibacterial activity of N,N′-diaryl-2-aryl-6-hydroxy-6-methyl-4-oxocyclohexane-1,3-dicarboxamides

Cited by 17 publications

References 2 publications

&lt;i&gt;β&lt;/i&gt;-Oxoanilides in Heterocyclic Synthesis: Synthesis and Antimicrobial Activity of Pyridines, Pyrans, Pyrimidines and Azolo, Azinopyrimidines Incorporating Antipyrine Moiety

&lt;i&gt;β&lt;/i&gt;-Oxoanilides in Heterocyclic Synthesis: Synthesis and Antimicrobial Activity of Pyridines, Pyrans, Pyrimidines and Azolo, Azinopyrimidines Incorporating Antipyrine Moiety

Synthesis of Pyridine-Dicarboxamide-Cyclohexanone Derivatives: Anticancer and α-Glucosidase Inhibitory Activities and In Silico Study

Synthesis and Antimicrobial Activity of Novel Hydrazone and 1,2,4-Triazole-3-thione Derivatives

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<i>β</i>-Oxoanilides in Heterocyclic Synthesis: Synthesis and Antimicrobial Activity of Pyridines, Pyrans, Pyrimidines and Azolo, Azinopyrimidines Incorporating Antipyrine Moiety

<i>β</i>-Oxoanilides in Heterocyclic Synthesis: Synthesis and Antimicrobial Activity of Pyridines, Pyrans, Pyrimidines and Azolo, Azinopyrimidines Incorporating Antipyrine Moiety