Novel High Energy Intermediate Analogues with Triazasterol-related Structures as Inhibitors of the Ergosterol Biosynthesis V [1]. Synthesis of Hexahydro-5H-imidazo[1?, 2?: 1,2]pyrimido-[4,3-a]isoquinolines and 1-Alkyl Analogues Representing New 8,13,15-Triazasteroids

Autor: Asbjörn Punkenhofer, Edith Gößnitzer
Rok vydání: 2003
Předmět:
Zdroj: Monatshefte f�r Chemie / Chemical Monthly. 134:1271-1282
ISSN: 1434-4475
0026-9247
DOI: 10.1007/s00706-003-0038-9
Popis: The synthesis of 1,2,6,10b,11,12-hexahydro-5H-imidazo[1′,2′:1,2]pyrimido[4,3-a]isoquinolines representing new types of 8,13,15-triazasteroids is described. The tetracyclic title compounds were prepared from 4-(2-hydroxyalkylamino)tetrahydro-2H-pyrimidoisoquinolines, which furnish after conversion to the corresponding bromoalkylamino compounds and base-catalyzed intramolecular nucleophilic displacement cyclization of the latter the desired 1-substituted 8,13,15-triazasteroids with aromatic ring A. The structures of the compounds were proved and assigned on the basis of homo- and heteronuclear correlated 1D and 2D NMR experiments. The title compounds represent triaza-analogues of selected high energy intermediates (HEI) of steroidal substrates formed during the enzymatic transformation of squalene into ergosterol and are designed to act as inhibitory mimicries of HEIs and potential antimycotics.
Databáze: OpenAIRE
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