Azulene analogs of pharmacologic agents I: Amides

✍ Scribed by Peter H. Doukas; Tully J. Speaker

• Book ID: 102913621
• Publisher: John Wiley and Sons
• Year: 1971
• Tongue: English
• Weight: 707 KB
• Volume: 60
• Category: Article
• ISSN: 0022-3549
• DOI: 10.1002/jps.2600600204

✦ Synopsis

The paper describes the synthesis of 15 azulene analogs of the benzenoid pharmacologic agent procainamide as part of a study of the pharmacodynamic effects of nonbenzenoid aromatic compounds. Three distinct series of compounds were prepared: azulene-L-carboxamides, l-(3-nitroazulene)-carboxamides, and 1-(3-acetamidoazulene)-carboxamides. The preparation of 3-nitro-photometry-structure azuloic acid, a new azulene intermediate, is also described. Keyphrases 0 Procainamide azulene analogs-synthesis 0 Azulene analogs, procainamide-synthesis 0 Column chromatographyseparation a IR spectrophotometry-structure I J UV spectro-

It is recognized that the presence of aromatic moieties in pharmacodynamic entities of varying specific activity may be prerequisite for optimal activity. These aromatic functions are, for the most part, benzenoid in nature. Several cyclic systems exist which show aromaticity but which are not benzenoid in character (1). Among these, azulene (isomeric to naphthalene), by virtue of its totally hydrocarbon nature, closely resembles benzene and its derivatives but differs in that it has a dipole moment, is a nonalternant hydrocarbon, has a resonance energy ' CHi--CH, 235