Synthesis of ABC analogues of the antitumour antibiotic streptonigrin

Marc Kimber; Pia I. Anderberg; Margaret M. Harding

doi:10.1016/S0040-4020(00)00267-2

Synthesis of ABC analogues of the antitumour antibiotic streptonigrin

Marc Kimber
, Pia I. Anderberg
, Margaret M. Harding

Research output: Contribution to journal › Article › peer-review

28 Citations (Scopus)

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.

Original language	English
Pages (from-to)	3575-3581
Number of pages	7
Journal	Tetrahedron
Volume	56
Issue number	22
DOIs	https://doi.org/10.1016/S0040-4020(00)00267-2
Publication status	Published - 26 May 2000
Externally published	Yes

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10.1016/S0040-4020(00)00267-2

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title = "Synthesis of ABC analogues of the antitumour antibiotic streptonigrin",

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.",

keywords = "Antitumour compounds, Bicyclic heterocyclic compounds, Coupling reactions, Quinolinones",

author = "Marc Kimber and Anderberg, \{Pia I.\} and Harding, \{Margaret M.\}",

year = "2000",

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doi = "10.1016/S0040-4020(00)00267-2",

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T1 - Synthesis of ABC analogues of the antitumour antibiotic streptonigrin

AU - Kimber, Marc

AU - Anderberg, Pia I.

AU - Harding, Margaret M.

PY - 2000/5/26

Y1 - 2000/5/26

N2 - 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.

AB - 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.

KW - Antitumour compounds

KW - Bicyclic heterocyclic compounds

KW - Coupling reactions

KW - Quinolinones

UR - https://www.scopus.com/pages/publications/0034717128

U2 - 10.1016/S0040-4020(00)00267-2

DO - 10.1016/S0040-4020(00)00267-2

M3 - Article

SN - 0040-4020

VL - 56

SP - 3575

EP - 3581

JO - Tetrahedron

JF - Tetrahedron

IS - 22

ER -

Synthesis of ABC analogues of the antitumour antibiotic streptonigrin

Abstract

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