title: Detour of prenostodione synthesis towards pyrazolones for antibacterial activity.
abstract: Our attempts to prepare indolyl acid (3), enroute to prenostodione (2), from phenyl-hydrazine following a reported procedure of Fischer-Indole synthesis rather lead to ethyl 2-(5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-3-yl)acetate as a major product, which underwent facile condensation with aldehydes to provide the pyrazolones. Intrigued by the opportunity for the diversity oriented synthesis of substituted pyrazolones, we have developed a facile one pot approach for pyrazolones and screened for antibacterial activity and, herein, results are reported.
authors.affiliation: Department of Chemistry and Biochemistry, University of Massachusetts Dartmouth, North Dartmouth, MA 02747, USA. srasapalli@umassd.edu
authors.forename: Sivappa
authors.initials: S
authors.lastname: Rasapalli
authors.forename: Yingjun
authors.initials: Y
authors.lastname: Fan
authors.forename: Menglong
authors.initials: M
authors.lastname: Yu
authors.forename: Christiaan
authors.initials: C
authors.lastname: Rees
authors.forename: John T
authors.initials: JT
authors.lastname: Harris
authors.forename: James A
authors.initials: JA
authors.lastname: Golen
authors.forename: Jerry P
authors.initials: JP
authors.lastname: Jasinski
authors.forename: Arnold L
authors.initials: AL
authors.lastname: Rheingold
authors.forename: Steven M
authors.initials: SM
authors.lastname: Kwasny
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Opperman
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D008968:Molecular Conformation; D010636:Phenols / Q000737:chemistry; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D047069:Pyrazolones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects; D013212:Staphylococcus epidermidis / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D007211:Indoles; D010636:Phenols; D047069:Pyrazolones; C430189:prenostodione; C083368:scytonemin