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Syntheses of Selected Quaternary Phenacylbromopyridinium Compounds and their Biological Evaluation

  • Khalid M. Khan EMAIL logo , Zafar S. Saifyb , Zeeshan , Abdullah Khan , Mansoor Ahmed , Muhammed Saeed , Raid J. Abdel-Jalil , Gerald Griibler and Wolfgang Voelter
Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 54 Issue 9

The studies, presented here, deal with the synthetic modification of 5-bromonicotinic acid on its nitrogen nucleus. The synthetic transformations were carried out by reacting equimolar amounts of 5-bromonicotinic acid and phenacyl halides in acetone. A range of phenacyl halides were used with the objective of getting a variety of quaternary ammonium salts of 5- bromonicotinic acid derivatives as multipurpose biologically active compounds. Twelve quaternary ammonium salts of 5-bromonicotinic acid have been synthesized and tested for cytotoxicity, antibacterial and antifungal activities. These compounds showed promising cytotoxicity against Artemia salina. Two compounds, 3-carboxy-1-(4′-methylphenacyl)-5-bromopyridinium bromide (2) and 3-carboxy-1-(4′-nitrophenacyl)-5-bromopyridinium bromide (12), were highly active against Gram-positive and Gram-negative bacteria among all the tested compounds. All the compounds were examined for antifungal activity against fifteen fungal cultures, but none of these compounds proved to be effective against these fungi. The parent compounds and its derivatives were also examined for their effect on mean arterial blood pressure in anaesthetized rats. Compounds 7 and 8 were found to be twofold more active than the parent compound. The rest of the products showed blood pressure lowering effects comparable to the parent compound. All compounds were characterised via elemental analysis UV, IR , mass and 1H NMR spectroscopy.

Keywords: 5-Bromonicotinic Acid. Cytotoxicity. Antimicrobial Activity; Blood Pressure Activity
Received: 1999-6-8
Published Online: 2014-6-2
Published in Print: 1999-9-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Die Kristallstruktur von [PhMe3 N]4 [Pb3Br10] / Crystal Structure of [PhMe3N]4[Pb3B r10]
  2. Hexaborate Cluster Radical Anions [B6Haln Hal'6-n].- and [B6Hal5R].-(Hai, Hal' = CI, Br, I; R = H, alkyl). Chemical or Electrochemical Generation, Vibrational, UV-Vis and EPR Spectroscopy
  3. Schwingungsspektren und Normalkoordinatenanalysen der Dioxoosmate( VI) trans-[OsO2(CN)4]2-, trans-[OsO2(CN)2(0H )]22- und trans-[OsO2(CN)2(OCH3)]22 sowie Kristallstruktur von trans-(Ph3PNPPh3)2[OsO2(CN)2(OCH3)]2 / Vibrational Spectra and Normal Coordinate Analysis of the Dioxoosmates(VI) trans-[OsO2(CN)4]2-, trans-[OsO2 (CN)2(OH)]22- and trans-[OsO2(CN)2(OCH3]22- , and Crystal Structure of trans-(Ph3PNPPh3)2[OsO2(CN)2(OCH3)]2
  4. Darstellung, Schwingungsspektren und Normalkoordinatenanalysen der Dioxoosmate(VI) trans-[OsO2(CN)2(ox)]2-, transs-[OsO2(CN)2(mal)]2- und trans-[OsO2(CN)2(N2H2C2O2)]2- / Synthesis, Vibrational Spectra and Normal Coordinate Analysis of the Dioxoosmates(VI) frans-[OsO2(CN)2(ox)]2- , trans-[OsO2 (CN)2(mal)]2- and trans-[OsO2 (CN)2(N2H2C2O2)]2-
  5. Structure of [μ-S2{Ru(PCy3)('S4')}2] · 2.5 THF ·0.5 Et2O Containing Homochiral Metal Complex Fragments ['S4'2- = 1,2-Bis(mercaptophenylthio)-ethane (2-)]
  6. The Crystal Structure of WC Type ZrTe. Advantages in Chemical Bonding as Contrasted to NiAs Type ZrTe
  7. Wrap-around Encapsulated Cs(dibenzo-24-crown-8)+ Cations form Linear Coordination Polymers with Dicyanoargentate Anions Ag(CN)2-
  8. Reaktionsverhalten von β-Oxo-carbonsäurederivaten der Anthracenreihe bei der Synthese von Pyrazolen / On the Reaction Behavior of ß-Oxo Carbonic Acid Derivatives of the Anthracene Series in Pyrazole Synthesis
  9. Electrochemical Electron Transfer Reactions of M(ttcn)23+/2+ (M = Co, Pd, Pt, Au; ttcn = 1,4,7-trithiacyclononane): the Relation of Reaction Volumes and Electron Transfer Rate Constants
  10. Tuning the Energy of the NIR Absorption of Dinuclear Triphos-Cobalt-Complexes
  11. Structure and Properties of the Stannide Eu2Au2Sn5, and its Relationship with the Family of BaAl4-Related Structures
  12. 2-[N,N-Bis(trimethylstannyl)amino]pyridine and Bis[N-(N-trimethyIsiIyI- 2-aminopyridyI)]dimethyltin - Intramolecular N-Sn Co-ordination
  13. Preparation and X-Ray Structure of 4-N,N′-Bis(trimethylsilyl)- amino-3,5-diisopropylphenylselenium Trichloride
  14. One- and Two- Dimensional Copper(I) Halide Based Coordination Polymers with Bridging Pyridazine or Pyrimidine Ligands
  15. Methoxyalky 1-funktionalisierte 2,3-Dihy droimidazol-2-ylidene [1] / Methoxyalkyl Functionalized 2,3-Dihydroimidazol-2-ylidenes [1]
  16. Synthesis and Reactivity of Novel Bis(stannyl)silanes
  17. Cinnamoylacetonitrile in Heterocyclic Synthesis, Part 7 [1]. Simple Synthesis of Benzothiazepines, Pyrones and Oxazolopyridine
  18. Synthesis of 3-Phenylisoxazolo[3,4-a]carbazoles
  19. New Simple and One-Pot Synthetic Routes to Polyfunctionally Substituted Pyridines; 1,4-Dihydropyridazines and 4H-1,2-Oxazine
  20. Syntheses of Selected Quaternary Phenacylbromopyridinium Compounds and their Biological Evaluation
https://doi.org/10.1515/znb-1999-0920
Keywords for this article
5-Bromonicotinic Acid. Cytotoxicity. Antimicrobial Activity; Blood Pressure Activity

Articles in the same Issue

  1. Die Kristallstruktur von [PhMe3 N]4 [Pb3Br10] / Crystal Structure of [PhMe3N]4[Pb3B r10]
  2. Hexaborate Cluster Radical Anions [B6Haln Hal'6-n].- and [B6Hal5R].-(Hai, Hal' = CI, Br, I; R = H, alkyl). Chemical or Electrochemical Generation, Vibrational, UV-Vis and EPR Spectroscopy
  3. Schwingungsspektren und Normalkoordinatenanalysen der Dioxoosmate( VI) trans-[OsO2(CN)4]2-, trans-[OsO2(CN)2(0H )]22- und trans-[OsO2(CN)2(OCH3)]22 sowie Kristallstruktur von trans-(Ph3PNPPh3)2[OsO2(CN)2(OCH3)]2 / Vibrational Spectra and Normal Coordinate Analysis of the Dioxoosmates(VI) trans-[OsO2(CN)4]2-, trans-[OsO2 (CN)2(OH)]22- and trans-[OsO2(CN)2(OCH3]22- , and Crystal Structure of trans-(Ph3PNPPh3)2[OsO2(CN)2(OCH3)]2
  4. Darstellung, Schwingungsspektren und Normalkoordinatenanalysen der Dioxoosmate(VI) trans-[OsO2(CN)2(ox)]2-, transs-[OsO2(CN)2(mal)]2- und trans-[OsO2(CN)2(N2H2C2O2)]2- / Synthesis, Vibrational Spectra and Normal Coordinate Analysis of the Dioxoosmates(VI) frans-[OsO2(CN)2(ox)]2- , trans-[OsO2 (CN)2(mal)]2- and trans-[OsO2 (CN)2(N2H2C2O2)]2-
  5. Structure of [μ-S2{Ru(PCy3)('S4')}2] · 2.5 THF ·0.5 Et2O Containing Homochiral Metal Complex Fragments ['S4'2- = 1,2-Bis(mercaptophenylthio)-ethane (2-)]
  6. The Crystal Structure of WC Type ZrTe. Advantages in Chemical Bonding as Contrasted to NiAs Type ZrTe
  7. Wrap-around Encapsulated Cs(dibenzo-24-crown-8)+ Cations form Linear Coordination Polymers with Dicyanoargentate Anions Ag(CN)2-
  8. Reaktionsverhalten von β-Oxo-carbonsäurederivaten der Anthracenreihe bei der Synthese von Pyrazolen / On the Reaction Behavior of ß-Oxo Carbonic Acid Derivatives of the Anthracene Series in Pyrazole Synthesis
  9. Electrochemical Electron Transfer Reactions of M(ttcn)23+/2+ (M = Co, Pd, Pt, Au; ttcn = 1,4,7-trithiacyclononane): the Relation of Reaction Volumes and Electron Transfer Rate Constants
  10. Tuning the Energy of the NIR Absorption of Dinuclear Triphos-Cobalt-Complexes
  11. Structure and Properties of the Stannide Eu2Au2Sn5, and its Relationship with the Family of BaAl4-Related Structures
  12. 2-[N,N-Bis(trimethylstannyl)amino]pyridine and Bis[N-(N-trimethyIsiIyI- 2-aminopyridyI)]dimethyltin - Intramolecular N-Sn Co-ordination
  13. Preparation and X-Ray Structure of 4-N,N′-Bis(trimethylsilyl)- amino-3,5-diisopropylphenylselenium Trichloride
  14. One- and Two- Dimensional Copper(I) Halide Based Coordination Polymers with Bridging Pyridazine or Pyrimidine Ligands
  15. Methoxyalky 1-funktionalisierte 2,3-Dihy droimidazol-2-ylidene [1] / Methoxyalkyl Functionalized 2,3-Dihydroimidazol-2-ylidenes [1]
  16. Synthesis and Reactivity of Novel Bis(stannyl)silanes
  17. Cinnamoylacetonitrile in Heterocyclic Synthesis, Part 7 [1]. Simple Synthesis of Benzothiazepines, Pyrones and Oxazolopyridine
  18. Synthesis of 3-Phenylisoxazolo[3,4-a]carbazoles
  19. New Simple and One-Pot Synthetic Routes to Polyfunctionally Substituted Pyridines; 1,4-Dihydropyridazines and 4H-1,2-Oxazine
  20. Syntheses of Selected Quaternary Phenacylbromopyridinium Compounds and their Biological Evaluation
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