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Synthesis of ABC Analogues of the Antitumour Antibiotic Streptonigrin

✍ Scribed by Marc Kimber; Pia I. Anderberg; Margaret M. Harding

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
122 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

AbstractÐABC 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-6methoxy-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.

πŸ“œ SIMILAR VOLUMES

Assignment of the 13C and 15N NMR spectr
Assignment of the 13C and 15N NMR spectra of the antitumour antibiotic streptonigrin
✍ Pia I. Anderberg; Ian J. Luck; Margaret M. Harding πŸ“‚ Article πŸ“… 2002 πŸ› John Wiley and Sons 🌐 English βš– 92 KB

## Abstract The assignments of the two pyridyl nitrogens and two amino nitrogens in the antitumour antibiotic streptonigrin, and all carbon resonances, were determined by ^15^N (HSQC, HMBC) and ^13^C (HSQC, HMBC) NMR techniques. These data provide useful probes for determination of the site(s) of m