A novel synthesis of dibenzo[c,f]chromenes, dibenzo[c,h]chromenes and benzo[7,8]chromeno[3,4-f]isoindoles as antimicrobial agents.
Naphtho[2,1-b]pyranone (3) was allowed to react with arylmethylenemalononitriles to yield 4-amino-5-oxo-2-aryl-5H-dibenzo[c,f]chromene-3-carbonitriles (4a,b); with ethyl 3,4-dichlorobenzylidene cyanoacetate to furnish dibenzo[c,f]chromene (5) and with elemental sulfur in dioxane containing piperidine to give thieno[3,4-d]naphtho[2,1-b]pyranone (6). Similarly, naphtho[1,2-b]pyranone (7) was reacted with arylmethylenemalononitriles and elemental sulfur to furnish dibenzo[c,h]chromenes (8) and thieno[3,4-d]naphtho[1,2-b]pyranone (10), respectively. Compound 10 underwent cycloaddition with N-arylmaleimides to yield benzo[7,8]chromeno[3,4-f]isoindoles (11a-c). Some of these compounds were screened in vitro for their antimicrobial activities.
el-Gaby
M S
MS
Chemistry Department, Faculty of Science, Al-Azhar University at Assiut, Egypt. m_elgaby@hotmail.com
Zahran
M A
MA
Ismail
M M
MM
Ammar
Y A
YA
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D013055:Spectrophotometry, Infrared; D013211:Staphylococcus aureus / Q000187:drug effects
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D001578:Benzopyrans; D007211:Indoles