Naturstoffchemie 110. Mitt.: Synthese des 1‐Hydroxy‐7‐methoxyacridons aus <i>Boenninghausenia albiflora REICHB</i>. (Rutaceae); Darstellung einiger einfacher Hydroxy‐, Methoxy‐ und Nitroacridone

Reisch, J.; Probst, Wiltrud

doi:10.1002/ardp.198700010

Cited by 7 publications

(3 citation statements)

References 7 publications

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“…The title compound was obtained from 6oo by method G, but the mixture was stirred for 1.5 h. The crude product was refluxed in toluene (DeaneStark). Then it was filtered by suction, washed with petroleum ether (3 Â 100 mL), and purified by column chromatography (SiO 2 ; CH 2 Cl 2 /MeOH, 95/5) to provide light-yellow crystals; 64% yield; mp 298 C; 1 H NMR (DMSO-d 6 , hydroxylimine tautomer) Analogously, methoxy-substituted acridones 5e [29], 5f [53], 5g [29], 5h [29], 5j [20], 5m [54], 5p [55] and 5r [47] and 5ss [30] were prepared by method G.…”

Section: 8-dimethoxy-10h-acridin-9-one (5)mentioning

confidence: 99%

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Structure–activity relationship studies of acridones as potential antipsoriatic agents. 1. Synthesis and antiproliferative activity of simple N-unsubstituted 10H-acridin-9-ones against human keratinocyte growth

Putic

Stecher

Prinz

et al. 2010

European Journal of Medicinal Chemistry

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A series of N-unsubstituted hydroxy-10H-acridin-9-ones were synthesized and evaluated for inhibitory action against HaCaT keratinocyte growth, in order to explore their potential as antipsoriatic agents. For structure-activity relationship studies, the number and position of the hydroxyl groups were modified, the oxygen functions substituted or replaced, or additional functional groups were introduced into the acridone scaffold. 1,8-Dihydroxy-10H-acridin-9-one (4), which is an aza-analogue of the antipsoriatic anthralin, was only marginally active. However, 1,3-dihydroxy-substituted 5ee was the most potent acridone within this series and inhibited keratinocyte growth with an IC(50) value comparable to that of anthralin. In contrast to anthralin, nearly all members of the acridone series were devoid of radical generating properties, which were determined by their capability to interact with the free radical 2,2-diphenyl-1-picrylhydrazyl. Structures with a phenolic hydroxyl or an aromatic amine arranged ortho or para to the acridone NH group were exceptions. Also in contrast to anthralin, membrane-damaging effects as documented by the release of lactate dehydrogenase into the culture medium were not observed for acridones.

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Section: 8-dimethoxy-10h-acridin-9-one (5)mentioning

confidence: 99%

“…Substitution pattern AA a IC 50 (mM) Acridones 5b [20], 5c [44], 5d [45], 5l [46], 5q [47], 5s [48], and 5v [49] were prepared from the corresponding methyl ethers (5f, 5g, 5h, 5m, 5r, 5t, and 5w, respectively) by method A. 1,8-dihydroxy-4-methoxy-10H-acridin-9-one (5y).…”

Section: Compoundsmentioning

confidence: 99%

Structure–activity relationship studies of acridones as potential antipsoriatic agents. 1. Synthesis and antiproliferative activity of simple N-unsubstituted 10H-acridin-9-ones against human keratinocyte growth

Putic

Stecher

Prinz

et al. 2010

European Journal of Medicinal Chemistry

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“…(4). The route a corresponds to Ullmann-Jourdan reaction [18,[28][29][30][31][32], which utilizes copper catalysts at high temperature, e.g. reflux in amyl alcohol [33].…”

Section: Syntheses Of 9-aminoacridines and Their Conjugatesmentioning

confidence: 99%

A Role of the 9-Aminoacridines and their Conjugates in a Life Science

Šebestı́k¹,

Hlaváček²,

Stibor

2007

CPPS

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The 9-aminoacridines play an important role in medicine. They were applied first in a treatment of protozoal infections in the beginning of the last century. Recently, it has been shown that the 9-aminoacridines are successful candidates for treatment of cancer, viral and prion diseases. Their conjugation with biomolecules such as peptides and proteins may modulate their activity, bioavailability and applicability. This review deals with the synthesis of 9-aminoacridine, its conjugation with variety of molecules and utilization of such conjugates in several fields of science.

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Synthese und cytostatische Wirkung des 9‐Nitronoracronycins

Reisch

Probst

1989

Archiv der Pharmazie

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Naturstoffchemie 110. Mitt.: Synthese des 1‐Hydroxy‐7‐methoxyacridons aus Boenninghausenia albiflora REICHB. (Rutaceae); Darstellung einiger einfacher Hydroxy‐, Methoxy‐ und Nitroacridone

Abstract: Über eine modifizierte Ullmann‐Synthese wurden die Acridone 5 dargestellt. Die 1‐Hydroxy‐7‐methoxyacridon‐Struktur für ein Alkaloid aus Boenninghausenia albiflora REICHB. konnte durch Synthese bestätigt werden.

Cited by 7 publications

References 7 publications

Structure–activity relationship studies of acridones as potential antipsoriatic agents. 1. Synthesis and antiproliferative activity of simple N-unsubstituted 10H-acridin-9-ones against human keratinocyte growth

Structure–activity relationship studies of acridones as potential antipsoriatic agents. 1. Synthesis and antiproliferative activity of simple N-unsubstituted 10H-acridin-9-ones against human keratinocyte growth

A Role of the 9-Aminoacridines and their Conjugates in a Life Science

Synthese und cytostatische Wirkung des 9‐Nitronoracronycins

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