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Synthesis of ABC Analogues of the Antitumour Antibiotic Streptonigrin

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Date

2000

Authors

Kimber, Marc C
Anderberg, Pia I
Harding, Margaret

Journal Title

Journal ISSN

Volume Title

Publisher

Elsevier

Abstract

ABC analogues of the antitumour antibiotic streptonigrin, that contain the key metal chelation site and redox-active quinone unit that are essential for biological activity, were prepared via palladium catalysed cross-coupling of 2-iodo-8-nitroquinoline or 2-iodo-6-methoxy-5-nitroquinoline with 2- trimethylstannio-6-methylpyridine. Mild oxidation of the pyridyl methyl group introduced the acid functional group on ring C and Fremy's salt oxidation afforded the quinone unit which was elaborated to give the 5-amino-6-methoxy substitution pattern present in streptonigrin. 2000 Elsevier Science Ltd.

Description

Keywords

Keywords: antineoplastic antibiotic; palladium complex; rufocromomycin; rufocromomycin derivative; unclassified drug; article; catalyst; drug structure; drug synthesis; oxidation; priority journal; structure activity relation; structure analysis Antitumour compounds; Bicyclic heterocyclic compounds; Coupling reactions; Quinolinones

Citation

URI

http://hdl.handle.net/1885/73506

Collections

ANU Research Publications

Source

Tetrahedron

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

Restricted until

2037-12-31

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