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Methyl 1-(7-acetamido-5,8-dimeth-oxy-quinolin-2-yl)-4-methyl-?-carboline-3-carboxyl-ate.

ABSTRACT: The title compound, C(27)H(24)N(4)O(5), is an inter-mediate in the synthesis of lavendamycin via a ruthenium-catalysed [2 + 2 + 2] cyclo-addition. An intra-molecular hydrogen-bond bridge from the carboline to the quinoline stabilizes a highly planar geometry [maximum deviation = 0.065?(6)?Å] for the two rigid units. This hydrogen-bond-stabilized coplanarity has a very close analogy in the structure of the anti-tumor anti-biotic streptonigrin in the solid state and in solution. Inter-molecular hydrogen-bond bridges of amides groups along the a axis and ?-? stacking inter-actions [centroid-centroid distance = 3.665?(9)?Å] connect mol-ecules arranged in a parallel manner.

SUBMITTER: Nissen F 

PROVIDER: S-EPMC3120419 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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Methyl 1-(7-acetamido-5,8-dimeth-oxy-quinolin-2-yl)-4-methyl-β-carboline-3-carboxyl-ate.

Nissen Felix F   Schollmeyer Dieter D   Detert Heiner H  

Acta crystallographica. Section E, Structure reports online 20110525 Pt 6

The title compound, C(27)H(24)N(4)O(5), is an inter-mediate in the synthesis of lavendamycin via a ruthenium-catalysed [2 + 2 + 2] cyclo-addition. An intra-molecular hydrogen-bond bridge from the carboline to the quinoline stabilizes a highly planar geometry [maximum deviation = 0.065 (6) Å] for the two rigid units. This hydrogen-bond-stabilized coplanarity has a very close analogy in the structure of the anti-tumor anti-biotic streptonigrin in the solid state and in solution. Inter-molecular hy  ...[more]

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