Synthesis and Biological Activity of Esters in the trans-1,2-Dihydroxy-1,2-dihydroacronycine Series

Permanganate oxidation of acronycine (1) led to keto alcohol 4 which could be reduced to trans-1,2-dihydroxy-1,2-dihydroacronycine (3) using NaBH4. Acylation of 3 afforded 12, 13, and 14. These esters (12, 13, and 14) were more potent than 1 when tested against L-1210 cells in vitro. Diacetate 12 wa...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1998-02, Vol.61 (2), p.198-201
Main Authors: Magiatis, Prokopios, Mitaku, Sofia, Skaltsounis, Alexios-Leandros, Tillequin, François, Koch, Michel, Pierré, Alain, Atassi, Ghanem
Format: Article
Language:English
Subjects:
Acronine - analogs & derivatives
Acronine - isolation & purification
Acronine - pharmacology
ACRONYCHIA BAUERI
AGENTES ANTINEOPLASTICOS
ALCALOIDE
ALCALOIDES
ALKALOIDS
Animals
ANTINEOPLASTIC AGENTS
Antineoplastic Agents, Phytogenic - isolation & purification
Antineoplastic Agents, Phytogenic - pharmacology
BIOCHEMICAL PATHWAYS
Biological and medical sciences
BIOSINTESIS
BIOSYNTHESE
BIOSYNTHESIS
Cell Cycle - drug effects
Cell Survival - drug effects
CHEMICAL COMPOSITION
CHEMICAL STRUCTURE
Chemotherapy
COMPOSICION QUIMICA
COMPOSITION CHIMIQUE
DRUG PLANTS
Drug Screening Assays, Antitumor
ESPECTROMETRIA
ESTER
ESTERES
ESTERS
ESTRUCTURA QUIMICA
Leukemia L1210 - drug therapy
Leukemia P388 - drug therapy
Medical sciences
MEDICAMENT CYTOSTATIQUE
Mice
OXIDACION
OXIDATION
OXYDATION
Pharmacology. Drug treatments
PLANTAS MEDICINALES
PLANTE MEDICINALE
Plants, Medicinal - chemistry
RUTACEAE
SPECTRAL ANALYSIS
SPECTROMETRIE
SPECTROMETRY
STRUCTURE CHIMIQUE
Tumor Cells, Cultured
VIA BIOQUIMICA DEL METABOLISMO
VOIE BIOCHIMIQUE DU METABOLISME
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Summary:Permanganate oxidation of acronycine (1) led to keto alcohol 4 which could be reduced to trans-1,2-dihydroxy-1,2-dihydroacronycine (3) using NaBH4. Acylation of 3 afforded 12, 13, and 14. These esters (12, 13, and 14) were more potent than 1 when tested against L-1210 cells in vitro. Diacetate 12 was evaluated in vivo against murine P-388 leukemia and was markedly active at a dose 16-fold lower than acronycine itself. Comparison of these results with those recently obtained in the cis-1,2-dihydroxy-1,2-dihydroacronycine series is discussed.
ISSN:0163-3864
1520-6025
DOI:10.1021/np970427s