TY - JOUR
T1 - Syntheses of selected quaternary phenacylbromopyridinium compounds and their biological evaluation
AU - Khan, Khalid M.
AU - Saify, Zafar S.
AU - Zeeshan, null
AU - Khan, Abdullah
AU - Ahmed, Mansoor
AU - Saeed, Muhammed
AU - Abdel-Jalil, Raid J.
AU - Grübler, Gerald
AU - Voelter, Wolfgang
N1 - Funding Information:
We express our gratitude to the Deutscher Akademischer Austauschdienst (DAAD, Bonn, Germany) for a short-term fellowship (41-HP-cr-gb) granted to Prof. Khalid M. Khan and to Fonds der Chemischen Industrie for financial support.
PY - 1999/9
Y1 - 1999/9
N2 - 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.
AB - 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.
KW - 5-Bromonicotinic Acid
KW - Antimicrobial Activity
KW - Blood Pressure Activity
KW - Cytotoxicity
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U2 - 10.1515/znb-1999-0920
DO - 10.1515/znb-1999-0920
M3 - Review article
AN - SCOPUS:0012243288
SN - 0932-0776
VL - 54
SP - 1210
EP - 1218
JO - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
JF - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
IS - 9
ER -