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Stereochemistry of the methyl­idene-bridged quinazoline-iso­quinoline alkaloid 3-{[6,7-dimeth­oxy-1-(4-nitro­phen­yl)-1,2,3,4-tetra­hydro­isoquinolin-2-yl]methyl­idene}-1,2,3,9-tetra­hydro­pyrrolo­[2,1-b]quinazolin-9-one methanol monosolvate

Two potentially bioactive fragments, namely a tricyclic quinazoline derivative with an exocyclic alkene moiety and a substituted iso­quinoline, are coupled to give 3-{[6,7-dimeth­oxy-1-(4-nitro­phen­yl)-1,2,3,4-tetra­hydro­isoquinolin-2-yl]methyl­idene}-1,2,3,9-tetra­hydro­pyrrolo­[2,1-b]quinazolin-...

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Detalles Bibliográficos
Autores principales: Tojiboev, Akmal, Zhurakulov, Sherzod, Vinogradova, Valentina, Englert, Ulli, Wang, Ruimin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7273985/
https://www.ncbi.nlm.nih.gov/pubmed/32523763
http://dx.doi.org/10.1107/S2056989020006696
Descripción
Sumario:Two potentially bioactive fragments, namely a tricyclic quinazoline derivative with an exocyclic alkene moiety and a substituted iso­quinoline, are coupled to give 3-{[6,7-dimeth­oxy-1-(4-nitro­phen­yl)-1,2,3,4-tetra­hydro­isoquinolin-2-yl]methyl­idene}-1,2,3,9-tetra­hydro­pyrrolo­[2,1-b]quinazolin-9-one. The target product crystallizes as a methanol solvate, C(29)H(26)N(4)O(5)·CH(4)O, and is E configured. The alternative Z isomer would necessarily imply either considerable twist about the central double bond or very unfavourable intra­molecular contacts between sterically more demanding substituents. The main residue and the co-crystallized solvent mol­ecule aggregate to discrete pairs via a classical O—H⋯O hydrogen bond with a distance of 2.8581 (7) Å between the methanol OH donor and the quinazolinone O=C acceptor.