Antitumour polycyclic acridines. Part 3.1 A two-step conversion of 9-azidoacridine to 7H-pyrido[4,3,2-kl ]acridines by Graebe–Ullmann thermolysis of substituted 9-(1,2,3-triazol-1-yl)acridines

Hagan, Damien J.; Chan, David C.; Schwalbe, Carl H.; Stevens, Malcolm F. G.

doi:10.1039/a707343g

Cited by 29 publications

(54 citation statements)

References 5 publications

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“…12 mp > 300°C dec). The product was identical (UV, IR, 1 H and 13 C NMR) to an authentic sample. 12 (ii) 9-(3-Aminoanilino)acridine (18c) 34 was converted to 9-(3-azidoanilino)acridine (18d) by sequential diazotization/azidation.…”

Section: Methodsmentioning

confidence: 99%

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Antitumor Polycyclic Acridines. 7. Synthesis and Biological Properties of DNA Affinic Tetra- and Pentacyclic Acridines

et al. 2000

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New synthetic routes to a series of tetra- and pentacyclic acridines related in structure to marine natural products are reported. The novel water-soluble agent dihydroindolizino[7,6,5-kl]acridinium chloride 14 has inhibitory activity in a panel of non-small-cell lung and breast tumor cell lines exceeding that of m-AMSA. The salt inhibited the release of minicircle products of kDNA confirming that disorganization of topoisomerase II partly underlies the activity of the compound. COMPARE analysis of the NCI mean graph profile of compound 14 at the GI(50) level corroborates this conclusion with Pearson correlation coefficients (>0.6) to clinical agents of the topoisomerase II class: however, this correlation was not seen at the LC(50) level. The inhibitory action of 14 on Saccharomyces cerevisiae transfected with human topoisomerase II isoforms showed a 3-fold selectivity against the IIalpha isoform over the IIbeta isoform. Unlike m-AMSA, 14 is not susceptible to P-glycoprotein-mediated drug efflux and retains activity in lung cells with derived resistance to the topoisomerase II inhibitor etoposide.

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Section: Methodsmentioning

confidence: 99%

“…The product was identical (UV, IR, 1 H and 13 C NMR) with an authentic sample. 13 8H-Quino[4,3,2-kl]acridine, 17a. A suspension of 9-(1,2,3-benzotriazol-1-yl)acridine (16a) (1.0 g) in triglyme (5 mL) was boiled (4 h) and the cooled solution was diluted with excess water.…”

Section: Methodsmentioning

confidence: 99%

Antitumor Polycyclic Acridines. 7. Synthesis and Biological Properties of DNA Affinic Tetra- and Pentacyclic Acridines

et al. 2000

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“…4‐Phenyl isomer 26 : yellow‐brown crystals, mp 248–250 °C (lit 23. 249–250 °C, but assigned to the 1,5‐isomer; lit 24.…”

Section: Methodsmentioning

confidence: 99%

“…The two triazoles are converted to the corresponding pyridoacridines on further heating 23. This reaction, too, is conveniently carried out by microwave irradiation (100 °C, 60 W, 60–90 min) in toluene solution.…”

Section: Methodsmentioning

confidence: 99%

9‐Azidoacridine and 9‐acridinylnitrene

Kvaskoff

Bernhardt

Wentrup

2010

J of Physical Organic Chem

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Matrix photolysis as well as flash vacuum thermolysis (FVT) of 9‐azidoacridine affords 9‐acridinylnitrene, which is characterized by its IR and ESR spectra and is photochemically inert. FVT above 600 °C yields a mixture of the five isomeric cyanocarbazoles. Microwave‐assisted reaction with diethyl‐ and dipropylamines in solution affords acridinylformamidine and acridinylpropionamidine, respectively. Microwave‐assisted reaction with dimethylamine causes nucleophilic displacement of the azido group. Microwave‐assisted 1,3‐dipolar cycloaddition with phenylacetylene yields the two regioisomeric 9‐(4‐ and 5‐phenyl‐1,2,3‐triazol‐1‐yl)acridines, whose structures were established by X‐ray crystallography. Copyright © 2010 John Wiley & Sons, Ltd.

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“…Stevens, University of Nottingham, according to methods described earlier. [8,9] The dry-state compound was stored in the dark at 4 8C. A stock solution of DH208 was prepared by dissolving the dry compound directly in water.…”

Section: Methodsmentioning

confidence: 99%

A Novel Methodological Approach for the Analysis of Host–Ligand Interactions

Strat¹,

Missailidis

Drake

2007

ChemPhysChem

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Traditional analysis of drug-binding data relies upon the Scatchard formalism. These methods rely upon the fitting of a linear equation providing intercept and gradient data that relate to physical properties, such as the binding constant, cooperativity coefficients and number of binding sites. However, the existence of different binding modes with different binding constants makes the implementation of these models difficult. This article describes a novel approach to the binding model of host-ligand interactions by using a derived analytical function describing the observed signal. The benefit of this method is that physically significant parameters, that is, binding constants and number of binding sites, are automatically derived by the use of a minimisation routine. This methodology was utilised to analyse the interactions between a novel antitumour agent and DNA. An optical spectroscopy study confirms that the pentacyclic acridine derivative (DH208) binds to nucleic acids. Two binding modes can be identified: a stronger one that involves intercalation and a weaker one that involves oriented outer-sphere binding. In both cases the plane of the bound acridine ring is parallel to the nucleic acid bases, orthogonal to the phosphate backbone. Ultraviolet (UV) and circular dichroism (CD) data were fitted using the proposed model. The binding constants and the number of binding sites derived from the model remained consistent across the different techniques used. The different wavelengths at which the measurements were made maintained the coherence of the results.

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Antitumour polycyclic acridines. Part 3.1 A two-step conversion of 9-azidoacridine to 7H-pyrido[4,3,2-kl ]acridines by Graebe–Ullmann thermolysis of substituted 9-(1,2,3-triazol-1-yl)acridines

Cited by 29 publications

References 5 publications

Antitumor Polycyclic Acridines. 7. Synthesis and Biological Properties of DNA Affinic Tetra- and Pentacyclic Acridines

Antitumor Polycyclic Acridines. 7. Synthesis and Biological Properties of DNA Affinic Tetra- and Pentacyclic Acridines

9‐Azidoacridine and 9‐acridinylnitrene

A Novel Methodological Approach for the Analysis of Host–Ligand Interactions

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