title: An efficient approach to the synthesis of highly congested 9,10-dihydrophenanthrene-2,4-dicarbonitriles and their biological evaluation as antimicrobial agents.
abstract: An efficient and novel method for the synthesis in moderate to good yield (72%-84%) of a series of 3-amino-1-substituted-9,10-dihydrophenanthrene-2,4-dicarbonitriles 1-5 via one-pot multi-component reactions of aldehydes, malononitrile, 1-tetralone and ammonium acetate has been delineated. Cyclocondensation attempts of aminocyanophenanthrene derivatives 1, 2, 4 and 5 with acetic anhydride in the presence of conc. H2SO4 failed and instead the diacetylamino derivatives 10-13 were obtained. All prepared compounds were structurally elucidated by various spectroscopic methods and X-ray crystallography. N,N-diacetylamino-derivatives of phenanthrene have shown good antimicrobial activity.
authors.affiliation: Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia. hfaidallahm@hotmail.com.
authors.forename: Hassan M
authors.initials: HM
authors.lastname: Faidallah
authors.forename: Khalid M A
authors.initials: KM
authors.lastname: Al-Shaikh
authors.forename: Tariq R
authors.initials: TR
authors.lastname: Sobahi
authors.forename: Khalid A
authors.initials: KA
authors.lastname: Khan
authors.forename: Abdullah M
authors.initials: AM
authors.lastname: Asiri
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D018360:Crystallography, X-Ray; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry*; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D000890:Anti-Infective Agents; D009570:Nitriles; D010616:Phenanthrenes; C031181:phenanthrene