Synthesis of chiral macrocyclic or linear pyridine carboxamides from pyridine-2,6-dicarbonyl dichloride as antimicrobial agents.
A series of chiral linear and macrocyclic bridged pyridines has been prepared starting from pyridine-2,6-dicarbonyl dichloride (2). The coupling of 1 with D-alanyl methyl ester gave 2,6-bis-D-alanyl pyridine methyl ester (3). Hydrazinolysis of 3 with hydrazine hydrate afforded bis-hydrazide 4. The latter was reacted with thiophene-2-carbaldehyde, phthalic anhydride or cyclohexanone to afford bis-carboxamide pyridine derivatives 5-7, respectively. Compound 4 was coupled with p-methoxy- or p-nitroaceto-phenone to yield compounds 8 and 9. In addition, 4 was reacted with 1,2,4,5-benzenetetra-carboxylic acid dianhydride or 1,4,5,8-naphthalenetetracarboxylic acid dianhydride to afford the macrocyclic octacarboxaamide pyridines 10 and 11. The detailed synthesis, spectroscopic data and antimicrobial screening for the synthesized compounds are reported.
Al-Salahi
Rashad A
RA
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia.
Al-Omar
Mohamed A
MA
Amr
Abd El-Galil E
Ael-G
D000577:Amides / Q000138:chemical synthesis*; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000577:Amides; D000890:Anti-Infective Agents; D011725:Pyridines