title: Synthesis, antimycobacterial and antifungal evaluation of some new 1-ethyl-5-(hetero)aryl-6-styryl-1,6-dihydropyrazine-2,3-dicarbonitriles.
abstract: The Petasis reaction of 6-hydroxy adducts of 1-alkyl-2,3-dicyano-5-arylpyrazinium salts with trans-styrylboronic acids proved to proceed smoothly at room temperature to give the corresponding 5-(hetero)aryl-6-styryl substituted 1,6-dihydropyrazine derivatives. Also it has been found that C(6) unsubstituted 1,6-dihydro- or 1,4,5,6-tetrahydropyrazine derivatives can be easy prepared in high yields from the corresponding pyrazinium salts by reduction with triethylsilane. All synthesized compounds were screened in vitro for their antifungal activities against seven pathogenic fungal strains and antimycobacterial activities against Mycobacterium tuberculosis H37Rv, avium, terrae and multi-drug-resistant strains isolated from tuberculosis patients in the Ural region (Russia).
authors.affiliation: I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Str., 22, Ekaterinburg 620041, Russia; Ural Federal University, Mira St. 19, Ekaterinburg 620002, Russia.
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 620041, 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: Ural Research Institute for Dermatology, Venereology and Immunopathology, Scherbakova St., 8, Ekaterinburg 620076, Russia.
authors.forename: Natal'ya P
authors.initials: NP
authors.lastname: Evstigneeva
authors.affiliation: Ural Research Institute for Dermatology, Venereology and Immunopathology, Scherbakova St., 8, Ekaterinburg 620076, Russia.
authors.forename: Nikolay V
authors.initials: NV
authors.lastname: Kungurov
authors.affiliation: Ural Research Institute for Dermatology, Venereology and Immunopathology, Scherbakova St., 8, Ekaterinburg 620076, Russia.
authors.forename: Natal'ya V
authors.initials: NV
authors.lastname: Zil'berberg
authors.affiliation: I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Str., 22, Ekaterinburg 620041, 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 620041, 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 620041, Russia; Ural Federal University, Mira St. 19, Ekaterinburg 620002, Russia.
authors.forename: Valery N
authors.initials: VN
authors.lastname: Charushin
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D024881:Drug Resistance, Bacterial / Q000187:drug effects; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D009169:Mycobacterium tuberculosis / Q000187:drug effects / Q000302:isolation & purification; D009570:Nitriles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D010084:Oxidation-Reduction; D011718:Pyrazinamide / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011719:Pyrazines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: C523085:1,6-dihydropyrazine-2,3-dicarbonitrile; D000935:Antifungal Agents; D000995:Antitubercular Agents; D009570:Nitriles; D011719:Pyrazines; D012821:Silanes; C512918:triethylsilane; D011718:Pyrazinamide
keywords: Antifungal activity; Antituberculosis activity; Petasis reaction; Pyrazine; Tuberculosis