title: A Novel Methodology for Synthesis of 1,5,6-Trisubstituted 2(1H)-Pyrazinones of Biological Interest.
abstract: In this report, we describe a new method for the synthesis of densely functionalized 2(1H)-pyrazinones. Treatment of mesoionic 1,3-oxazolium-5-olates with carbanions derived from activated methylene isocyanides (p-toluenesulfonylmethyl isocyanide (TosMIC) and ethyl isocyanoacetate) causes a novel ring transformation affording 2(1H)-pyrazinones in moderate to high yields. The cytotoxicity and antibacterial activity of some of the obtained products were studied and some of the products exhibited tumor-specific cytotoxicity.
authors.affiliation: Faculty of Pharmaceutical Sciences, Matsuyama University.
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Saijo
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Sekiya
authors.forename: Eiji
authors.initials: E
authors.lastname: Tamai
authors.forename: Ken-Ichi
authors.initials: KI
authors.lastname: Kurihara
authors.forename: Jun
authors.initials: J
authors.lastname: Maki
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Sakagami
authors.forename: Masami
authors.initials: M
authors.lastname: Kawase
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011719:Pyrazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D011719:Pyrazines