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Titolo:
Rates of reductive elimination of substituted nitrophenols from the (indol-3-yl)methyl position of indolequinones
Autore:
Swann, E; Moody, CJ; Stratford, MRL; Patel, KB; Naylor, MA; Vojnovic, B; Wardman, P; Everett, SA;
Indirizzi:
Mt Vernon Hosp, Gray Canc Inst, Northwood HA6 2JR, Middx, England Mt Vernon Hosp Northwood Middx England HA6 2JR od HA6 2JR, Middx, England Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England Univ Exeter Exeter Devon England EX4 4QD , Exeter EX4 4QD, Devon, England
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
fascicolo: 8, , anno: 2001,
pagine: 1340 - 1345
SICI:
1472-779X(2001):8<1340:ROREOS>2.0.ZU;2-G
Fonte:
ISI
Lingua:
ENG
Soggetto:
STRUCTURE-REACTIVITY CORRELATIONS; BIOREDUCTIVE ANTICANCER AGENTS; ANTITUMOR AGENTS; IN-VITRO; PULSE-RADIOLYSIS; ANION-RADICALS; HYPOXIA; ACTIVATION; ANALOGS; ELECTROCHEMISTRY;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
29
Recensione:
Indirizzi per estratti:
Indirizzo: Everett, SA Mt Vernon Hosp, Gray Canc Inst, POB 100, Northwood HA6 2JR, Middx, England Mt Vernon Hosp POB 100 Northwood Middx England HA6 2JR England
Citazione:
E. Swann et al., "Rates of reductive elimination of substituted nitrophenols from the (indol-3-yl)methyl position of indolequinones", J CHEM S P2, (8), 2001, pp. 1340-1345

Abstract

A series of indolequinones bearing substituted nitrophenols on the (indol-3-yl)methyl position was synthesised. The nitrophenol leaving groups were appropriately substituted to give a wide range (4 units) in phenolic pK(a) value. The rate of reductive elimination of phenoxide anions from the (indol-3-yl)methyl position of semiquinone radicals was dependent upon this pK(a), with a decrease in 3.8 pK units shortening the half-life from 28 to 1.5 ms. Only 2,4-dinitrophenol (pK(a)=3.9) was eliminated from an unsubstituted (indol-3-yl)methyl position at a rate that would compete with reoxidation of the radical by oxygen. A nitrothiophenol leaving group was eliminated comparatively slowly and only from the hydroquinone. These studies demonstratethe dependence upon leaving group pK(a) of the rate of reductive elimination from the (indol-3-yl)methyl position of indolequinones.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 09/04/20 alle ore 06:23:32