Research on potentially bioactive aza and thiaza polycyclic compounds containing a bridgehead nitrogen atom. Synthesis and antimicrobial activity of some pyrrolo[1,2,3-de]-1,4-benzothiazines, Part 2.
Acid catalyzed cyclization reactions of both 3-alkyl- and 3-aryl-substituted N-(2,2-dialkoxyethyl)-3,4-dihydro-2H-1,4-benzothiazines (2) lead to 2,3-dihydro-pyrrolo[1,2,3-de]-1,4-benzothiazines (3). The pyrrolobenzothiazine structure was deduced on the basis of 2D 1H NMR-NOESY experiments and fully determined by X-ray data. Compounds 3a-c showed poor antibacterial activity. However, the 3-phenyl-N-(2,2-dimethoxyethyl)-3,4-dihydro-2H-1,4-benzothiazine (2b') showed antifungal activity against Aspergillus niger 16-fold greater than miconazole.
Armenise
D
D
Dipartimento Farmaco-chimico, Facoltà di Farmacia, Università degli Studi di Bari, Italy.
Trapani
G
G
Stasi
F
F
Morlacchi
F
F
D000818:Animals; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D013329:Structure-Activity Relationship; D013843:Thiazines / Q000138:chemical synthesis / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D013843:Thiazines