title: Regiospecific Photocyclization of Mono- and Bis-Styryl-Substituted N-Heterocycles: A Synthesis of DNA-Binding Benzo[c]quinolizinium Derivatives.
abstract: Regiospecific C-N photocyclization of mono- and bis-styryl-substituted N-heterocycles was investigated. We demonstrated that the C-N regiospecificity of the photoinduced electrocyclization is a general feature of ortho-styryl-substituted N-heterocycles comprising one and two nitrogen atoms. This phototransformation provides a straightforward synthesis of the pharmaceutically important benzo[c]quinolizinium cation and its aza-analogues. Noticeably, bis-styryl derivatives undergo only one-fold cyclization with the second styryl fragment remaining uninvolved in the cyclization process. Photocyclization products of monostyryl derivativatives intercalate into calf thymus DNA (ct DNA), whereas photocyclization products of bis-styryl derivativatives possess a mixed binding mechanism with ct DNA. The results can be used for development of novel DNA-targeting chemotherapeutics based on benzo[c]quinolizinium derivatives.
authors: A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences , 28 Vavilova str., 119991 Moscow, Russia.|Department Chemie-Biologie, Organische Chemie II, Universität Siegen , Adolf-Reichwein-Str. 2, 57068 Siegen, Germany.
authors: Tseimur M
authors: TM
authors: Aliyeu
authors: A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences , 28 Vavilova str., 119991 Moscow, Russia.|Department Chemie-Biologie, Organische Chemie II, Universität Siegen , Adolf-Reichwein-Str. 2, 57068 Siegen, Germany.
authors: Daria V
authors: DV
authors: Berdnikova
authors: A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences , 28 Vavilova str., 119991 Moscow, Russia.
authors: Olga A
authors: OA
authors: Fedorova
authors: A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences , 28 Vavilova str., 119991 Moscow, Russia.
authors: Elena N
authors: EN
authors: Gulakova
authors: Department Chemie-Biologie, Organische Chemie II, Universität Siegen , Adolf-Reichwein-Str. 2, 57068 Siegen, Germany.
authors: Christopher
authors: C
authors: Stremmel
authors: Department Chemie-Biologie, Organische Chemie II, Universität Siegen , Adolf-Reichwein-Str. 2, 57068 Siegen, Germany.
authors: Heiko
authors: H
authors: Ihmels
mesh_terms: D016227:Benzoquinones / Q000737:chemistry*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D003500:Cyclization; D004247:DNA / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D010777:Photochemistry; D066244:Proton Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D020058:Styrene / Q000737:chemistry*
chemical_list: D016227:Benzoquinones; D006571:Heterocyclic Compounds; C004532:quinone; D020058:Styrene; D004247:DNA