PHOTOSWITCHABLE NINE-MEMBERED CYCLIC ENEDIYNES AND ENYNE-ALLENES

PHOTOSWITCHABLE NINE-MEMBERED CYCLIC ENEDIYNES AND ENYNE-ALLENES

CYCLOPROPENONE-CONTAINING CYCLIC ENEDIYNE AND ENYNE-ALLENE PRECURSORS AS PROTOTYPE PHOTOSWITCHABLE ANTITUMOR AGENTS

LAP Lambert Academic Publishing ( 29.03.2011 )

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The extreme cytotoxicity of natural enediyne antibiotics is attributed to the ability of the (Z)-3-ene-1,5-diyne fragment incorporated into a 10- or 9-membered ring cyclic system to undergo Bergman cyclization and producing dDNA-damaging p-benzyne diradical. The rate of this reaction strongly depends on the ring size. Thus 11-membered ring enediynes are stable, 10-membered ring analogs undergo slow cycloaromatization under ambient conditions or mild heating. Very little is known about reactivity of 9-membered ring enediynes due to their instability. We have developed thermally stable photo-precursors of 9-membered enediynes, in which one of the triple bonds is replaced by the cyclopropenone group. UV irradiation of the photo-precursor results in the efficient decarbonylation and the formation of reactive enediyne. The latter undergoes clean cycloaromatization spontaneously with absence of any chemical additives. Synthetic strategies of a series of cyclopropenone containing nine-membered enediyne precursors and DNA-cleavaging activity of the photo-generated enediynes have been also discussed.

Детали книги:

ISBN-13:

978-3-8443-2287-3

ISBN-10:

3844322876

EAN:

9783844322873

Язык книги:

English

By (author) :

Dr. Dinesh Pandithavidana

Количество страниц:

148

Опубликовано:

29.03.2011

Категория:

Органическая химия