Kinazolino-karbolinvázas alkaloidok 7-aza-analóg származékai. Szintézis, szerkezet, jellemzés

Translated title of the contribution: 7-Aza-analogs of quinazolino-carboline alkaloids. Synthesis, structure, characterisation

J. Kökösi, Á Kiss, R. Rotter, I. Hermecz, B. Noszál

Research output: Contribution to journalArticle

Abstract

The synthesis, structure and characterization of 8-substituted-7-azarutaecarpines (2) is described. These compounds were prepared by Fischer indolization of 3-amino-2-(1-phenylhydrazonoethyl)-4(3H)-quinazolin-one (5), followed by cyclocondensation with a series of aliphatic or aromatic aldehydes and formic acid or a Vilsmeyer-Haack reagent. The stereochemistry of compounds (2) was investigated by 1H nmr spectroscopy. It was found that the 8-substituents assume a quasi-axial position on the flattened boat conformation of ring C of (2), with the exception of ortho substituted phenyl groups, which occupy quasiequatorial position. Semiempirical MO calculations support these conformational preferences.

Original languageHungarian
Pages (from-to)187-195
Number of pages9
JournalActa pharmaceutica Hungarica
Volume70
Issue number3-6
Publication statusPublished - Dec 1 2000

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ASJC Scopus subject areas

  • Pharmaceutical Science

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