Synthesis and copper-dependent antimycoplasmal activity of 1-amino-3-(2-pyridyl)isoquinoline derivatives. 1. Amides.
In order to investigate the antimycoplasmal activity of compounds structurally related to 2,2'-bipyridyl, a series of both aliphatic and aromatic amides derived from 1-amino-3-(2-pyridyl)isoquinoline were synthesized. The most active compounds appeared to be as active as Tylosin, an antimycoplasmal therapeutic that is used in veterinary practice, in the presence of a small nontoxic amount of copper. Furthermore, it was found that antimycoplasmal activity depends on the hydrophobic fragmental value of amide residue. A quantitative structure-activity relationship established the optimal hydrophobic fragmental value of the amide residue to be 0.30.
de Zwart
M A
MA
Department of Pharmacochemistry, Vrije Universiteit, Amsterdam, The Netherlands.
van der Goot
H
H
Timmerman
H
H
D015082:2,2'-Dipyridyl; D000577:Amides / Q000138:chemical synthesis / Q000494:pharmacology; D000578:Amidines / Q000138:chemical synthesis / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003300:Copper / Q000378:metabolism*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000494:pharmacology; D007933:Leucomycins / Q000627:therapeutic use; D008826:Microbial Sensitivity Tests; D009174:Mycoplasma / Q000187:drug effects*; D011725:Pyridines / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D015645:Tylosin
D000577:Amides; D000578:Amidines; D000900:Anti-Bacterial Agents; D007546:Isoquinolines; D007933:Leucomycins; D011725:Pyridines; D015082:2,2'-Dipyridyl; D003300:Copper; D015645:Tylosin