Stereochemistry of the methyl-idene-bridged quinazoline-iso-quinoline alkaloid 3-{[6,7-dimeth-oxy-1-(4-nitro-phen-yl)-1,2,3,4-tetra-hydro-isoquinolin-2-yl]methyl-idene}-1,2,3,9-tetra-hydro-pyrrolo-[2,1-b]quinazolin-9-one methanol monosolvate.

ABSTRACT: Two potentially bioactive fragments, namely a tricyclic quinazoline derivative with an exocyclic alkene moiety and a substituted iso-quinoline, are coupled to give 3-{[6,7-dimeth-oxy-1-(4-nitro-phen-yl)-1,2,3,4-tetra-hydro-isoquinolin-2-yl]methyl-idene}-1,2,3,9-tetra-hydro-pyrrolo-[2,1-b]quinazolin-9-one. The target product crystallizes as a methanol solvate, C₂₉H₂₆N₄O₅·CH₄O, and is E configured. The alternative Z isomer would necessarily imply either considerable twist about the central double bond or very unfavourable intra-molecular contacts between sterically more demanding substituents. The main residue and the co-crystallized solvent mol-ecule 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.

SUBMITTER: Tojiboev A 

PROVIDER: S-EPMC7273985 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature