Anne-Marie Galy

Some new 1-nitro acridine derivatives as antimicrobial agents

Abstract Some new 1-nitro acridine derivatives were prepared and characterized. These compounds were screened for evaluating their antimicrobial properties against Gram+ bacteria, Gram − bacteria, and mycobacteria as well as fungi. With reference to the results obtained, 1-nitro-4-aminoethylamine-9-alkylthioacridines must be considered as promising lead molecules.

Antimicrobial activity of 9-oxo and 9-thio acridines: Correlation with intercalation into DNA and effects on macromolecular biosynthesis

The antimicrobial activity of several new 9-acridinones and 9-thioalkylacridines towards Escherichia coli, Staphylococcus aureus, Mycobacterium smegmatis and Candida albicans was investigated. Minimal inhibitory, bactericidal and fungicidal concentrations were determined using a microplate assay which enabled inhibitory, bactericidal and fungicidal indices to be calculated. These indices facilitated structure/activity relationship studies. DNA-intercalating capability and DNA supercoiling inhibitory effects as well as inhibitory effects on macromolecular synthesis were determined. Results showed that intercalation into DNA, which is the mechanism of action usually postulated for acridines, cannot be correlated with the properties examined. However, inhibition of RNA synthesis may be involved in the antimicrobial activity of the drugs.

13C-NMR Study of Some Substituted 9-Acridanone Derivatives

Abstract 13C-NMR spectra of several 9-acridanones with different substituents both on the ring (R1 = CH3, OCH3, NH2, N(CH3)2, NO2) and at the nitrogen atom (R2 = H, CH3 C2H5, CH2-C6H5, C[tbnd]C-CH3, (CH2)2N(C2H2)2, CH=C=CH2) have been recorded. The C-NMR chemical shifts are discussed as a function of the nature of the substituent, the importance of peri steric interactions and the electronic structure of the acridanone ring. There is a good linear relationship between the total electronic density and the chemical shifts.

New antiparasitic agents. III. Comparison between trypanocidal activities of some acridine derivatives against Trypanosoma cruzi in vitro.

Some acridine compounds referred to as 9-imino, 9-oxo and 9-thio derivatives were screened for activity against Trypanosoma cruzi in vitro. The results are discussed here with reference to the structure of the compounds tested. Attempts to elucidate the mode of action of active acridines are also included. The most active compounds that were tested were 9-thioacridanones and 9-thio-1,2,3,4-tetrahydroacridanones Added to this, the dialkylaminoalkylthio group seems to be the most convenient molecular moiety for trypanocidal activity in the 9-substituted acridine series.

A Carbon-13 NMR Study of the Structure of 9-Acridanone and 9-Thioacridanone in Neutral and Acidic Media

Abstract The antimicrobial and antiparasitic properties of acridine derivatives are known for a long time1; more recently their anticancer activity has been reported2. Amongst the acridines, the derivatives of 9-acridanone and of 9-thioacridanone have interesting properties3. Since these compounds show a problem of tautomerism4, it would be important to study their behaviour in order to understand the activity of acridanones and thioacridanones in media of different acidity. The present publication deals with the study, by means of 13C NMR, of the structure of compounds and (Figure 1) in DMSO-d 6 and in trifluoroacetic acid. Five other derivatives, to (Figure l), used as model compounds, were also studied in these conditions.

New Antiamebic Acridines

A series of novel 9-acridanones and 9-iminoacridines has been prepared and investigated by a number of spectroscopic techniques in order to determine the nature and extent of the binding of these compounds to DNA. Results are discussed with reference to antiamebic activity in vitro.

Antiamebic Activity of New Acridinic Derivatives against Naegleria and Acanthamoeba Species in vitro

In vitro antiamebic activity of selected acridine derivatives has been investigated against Naegleria and Acanthamoeba species. The most active compounds belong to the 9-thioacridanone and the 1,2,3,4-tetrahydro-9-thioacridanone series. In addition, some structure-activity relationships are proposed.

New α,ω-diamido and α,ω-diamino mono-and bi-bridged acridine dimers

A novel set of dimers derived from 9-amino acridine was prepared and characterized by1H and13CNMR. These derivatives are bridged at several different positions of the heterocyclic moieties, by the way of α,ω-diamido or α,ω-diamino side-chains. Additionally the preparation of some bi-bridged compounds was achieved.ZusammenfassungEs wurde eine neue Reihe von Dimeren des 9-Aminoacridins hergestellt und mittels1H und13C-NMR charakterisiert. Diese Derivate sind an verschiedenen Positionen des Heterocyclus mit α,ω-Diamido- oder α,ω-Diamino-Seitenketten überbrückt. Zusätzlich wurden auch einige zweifachüberbrückte Verbindungen hergestellt.

Reaction of 4-Hydroxyacridin-9(10H)-one and 4-Hydroxyacridine-9(10H)-thione with α,ω-Alkyl Dibromides

Summary. Starting from 4-hydroxyacridin-9(10H)-one (1) and 4-hydroxyacridine-9(10H)-thione (2), a series of bis-derivatives was prepared, among them the bridged bis-acridin-(10H)-ones 9–14 and the bis-mercapto-(9H)-acridines 15–18. The reactivity of the 2- and 4-hydroxy series was compared; it was found that it is harder to demethylate 4-methoxy derivatives than their 2-methoxy analogues.Zusammenfassung. Ausgehend von 4-Hydroxyacridin-9(10H)-on (1) und 4-Hydroxyacridin-9(10H)-thion (2) wurde eine Serie von bis-Derivaten, unter ihnen die verbrückten bis-Acridin-9(10H)-one 9–14 und die bis-Mercapto-(9H)-acridine 15–18, hergestellt. Die Reaktivität der 2- und 4-Hydroxyderivate wurde verglichen; es wurde festgestellt, daß die 4-Methoxyderivate schwerer zu demethylieren sind als die 2-Methoxyderivate.