Synthesis and antimicrobial activity of 4-hydroxy-4-(pyridyl)alk-3-en-2-ones

Riahi, Abdolmajid; Wurster, Martina; Lalk, Michael; Lindequist, Ulrike; Langer, Peter

doi:10.1016/j.bmc.2009.05.023

Cited by 11 publications

(10 citation statements)

References 11 publications

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“…However, two products (similar to 5 and 6) were obtained in previous work by others, in the "4-hydroxy-alk-3-en-2-one" tautomeric form under different conditions (NaH, Et2O, reflux) [18].…”

Section: Introductionmentioning

confidence: 61%

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Synthesis of Novel β-Keto-Enol Derivatives Tethered Pyrazole, Pyridine and Furan as New Potential Antifungal and Anti-Breast Cancer Agents

et al. 2015

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Abstract:Recently, a new generation of highly promising inhibitors bearing β-keto-enol functionality has emerged. Reported herein is the first synthesis and use of novel designed drugs based on the β-keto-enol group embedded with heterocyclic moieties such as pyrazole, pyridine, and furan, prepared in a one-step procedure by mixed Claisen condensation. All the newly synthesized compounds were characterized by FT-IR, 1 H-NMR, 13 C-NMR, ESI/LC-MS, elemental analysis, and evaluated for their in vitro antiproliferative activity against breast cancer (MDA-MB241) human cell lines and fungal strains (Fusarium oxysporum f.sp albedinis FAO). Three of the synthesized compounds showed potent activity against fungal strains with IC 50 values in the range of 0.055-0.092 µM. The results revealed that these compounds showed better IC 50 values while compared with positive controls.

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“…However, two products (similar to 5 and 6) were obtained in previous work by others, in the "4-hydroxy-alk-3-en-2-one" tautomeric form under different conditions (NaH, Et2O, reflux) [18].…”

Section: Introductionmentioning

confidence: 61%

“…The activity followed the structure activity relationships (SARs) and showed an interesting dependence on the substitution pattern. Considering the influence of substituent R, it was found that the phenyl residue leads to a stronger growth inhibition [18]. This was especially evident for products 6 and 10.…”

Section: Biological Activitiesmentioning

confidence: 92%

Synthesis of Novel β-Keto-Enol Derivatives Tethered Pyrazole, Pyridine and Furan as New Potential Antifungal and Anti-Breast Cancer Agents

et al. 2015

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“…7b was a yellow oil, and the spectroscopic data are consistent with data previously reported. 18 1 H NMR (400 MHz, CDCl 3 ) δ 15.96 (s, 1H), 9.08 (d, J = 1.6 Hz, 1H), 8.73 (dd, J = 1.6, 4.8 Hz, 1H), 8.16 (t, J = 2.0 Hz, 1H), 7.42−7.39 (m, 1H), 6.19 (s, 1H), 2.51 (q, J = 7.6 Hz, 2H), 1.23 (t, J = 7.6 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 198.8, 180.6, 152.6, 148.3, 134.4, 130.7, 123.5, 96.0, 32.5, 9.6.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Access to 8-Azachromones via Activation of C–H in N-Oxides

Wang

Feng

et al. 2017

J. Org. Chem.

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A concise and practical synthetic method has been developed for 8-azachromones, including 8-azaflavones, which have emerged as a promising class of compounds. Using commercially available nicotinates as the starting material, 8-azachromones were obtained in only three steps. The key intramolecular O-arylation reaction was achieved by nucleophilic attack of enolates to C2 of N-oxides under PyBrop or AcO activation conditions. These studies provide the basis for the access to 8-azachromones, enabling future work including the discovery and development of novel chromonoid drugs or other functional materials.

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“…In the last few years we and others reported a variety of synthesis of heteroaromatics that have been developed utilizing β-oxoanilides as readily obtainable compounds [7][8][9]. Due to the recent reported biological activities of the heterocyclic moieties mentioned here such as pyridine derivatives which posses antimicrobial [10], and fungicidal [11] activities. As well as, pyrimidine derivatives were reported to be showed antimicrobial [12], activity.…”

Section: Introductionmentioning

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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Synthesis and antimicrobial activity of 4-hydroxy-4-(pyridyl)alk-3-en-2-ones

Cited by 11 publications

References 11 publications

Synthesis of Novel β-Keto-Enol Derivatives Tethered Pyrazole, Pyridine and Furan as New Potential Antifungal and Anti-Breast Cancer Agents

Synthesis of Novel β-Keto-Enol Derivatives Tethered Pyrazole, Pyridine and Furan as New Potential Antifungal and Anti-Breast Cancer Agents

Access to 8-Azachromones via Activation of C–H in N-Oxides

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

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Synthesis and antimicrobial activity of 4-hydroxy-4-(pyridyl)alk-3-en-2-ones

Cited by 11 publications

References 11 publications

Synthesis of Novel β-Keto-Enol Derivatives Tethered Pyrazole, Pyridine and Furan as New Potential Antifungal and Anti-Breast Cancer Agents

Synthesis of Novel β-Keto-Enol Derivatives Tethered Pyrazole, Pyridine and Furan as New Potential Antifungal and Anti-Breast Cancer Agents

Access to 8-Azachromones via Activation of C–H in N-Oxides

&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

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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