title: Synthesis, and structure-activity relationship for C(4) and/or C(5) thienyl substituted pyrimidines, as a new family of antimycobacterial compounds.
abstract: Combination of the Suzuki cross-coupling and nucleophilic aromatic substitution of hydrogen (SN(H)) reactions proved to be a convenient method for the synthesis of C(4) and/or C(5) mono(thienyl) and di(thienyl) substituted pyrimidines from commercially available 5-bromopyrimidine. All new pyrimidines were found to be active in micromolar concentrations in vitro against H37Rv, avium, terrae, rifampicin and isoniazid-resistance strains of Mycobacterium tuberculosis. The data for acute in vivo toxicity in mice have been obtained for these compounds which appear to be promising antitubercular agents.
authors.affiliation: I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Str., 22, Ekaterinburg, 620137, Russia; Ural Federal University, Mira St. 19, Ekaterinburg, 620002, Russia. Electronic address: Verbitsky@ios.uran.ru.
authors.forename: Egor V
authors.initials: EV
authors.lastname: Verbitskiy
authors.affiliation: I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Str., 22, Ekaterinburg, 620137, Russia; Ural Federal University, Mira St. 19, Ekaterinburg, 620002, Russia.
authors.forename: Ekaterina M
authors.initials: EM
authors.lastname: Cheprakova
authors.affiliation: I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Str., 22, Ekaterinburg, 620137, Russia; Ural Federal University, Mira St. 19, Ekaterinburg, 620002, Russia.
authors.forename: Pavel A
authors.initials: PA
authors.lastname: Slepukhin
authors.affiliation: Ural Research Institute for Phthisiopulmonology, 22 Parts'ezda St., 50, Ekaterinburg, 620039, Russia.
authors.forename: Marionella A
authors.initials: MA
authors.lastname: Kravchenko
authors.affiliation: Ural Research Institute for Phthisiopulmonology, 22 Parts'ezda St., 50, Ekaterinburg, 620039, Russia.
authors.forename: Sergey N
authors.initials: SN
authors.lastname: Skornyakov
authors.affiliation: I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Str., 22, Ekaterinburg, 620137, Russia; Ural Federal University, Mira St. 19, Ekaterinburg, 620002, Russia.
authors.forename: Gennady L
authors.initials: GL
authors.lastname: Rusinov
authors.affiliation: I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Str., 22, Ekaterinburg, 620137, Russia; Ural Federal University, Mira St. 19, Ekaterinburg, 620002, Russia.
authors.forename: Oleg N
authors.initials: ON
authors.lastname: Chupakhin
authors.affiliation: I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Str., 22, Ekaterinburg, 620137, Russia; Ural Federal University, Mira St. 19, Ekaterinburg, 620002, Russia.
authors.forename: Valery N
authors.initials: VN
authors.lastname: Charushin
mesh_terms: D000818:Animals; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004351:Drug Resistance / Q000187:drug effects; D020128:Inhibitory Concentration 50; D051379:Mice; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013989:Ticrynafen / Q000737:chemistry*
chemical_list: D000995:Antitubercular Agents; D011743:Pyrimidines; D013989:Ticrynafen
keywords: Antimicobacterial; Cross-coupling; Nucleophilic aromatic substitution of hydrogen; Pyrimidine; Tuberculosis