Frameshift Mutagenicity and DNA Intercalation of 9-Amino-2-hydroxyacridine, a Rat Liver S9 Metabolite of 9-Aminoacridine

Regioselective Synthesis of 2-Imino-1,3-thiazolidin-4-ones by Treatment ofN-(Anthracen-9-yl)-N′-ethylthiourea with Bromoacetic Acid Derivatives

“…Structures incorporating the acridine moiety have shown marked mutagenic, [8] antiviral [9] and antitumour [10Ϫ13] activities, and so are of prime interest for pharmaceutical applications. In our previous studies on acridine, [14Ϫ20] the particular susceptibility of C-9 in acridine to nucleophilic attack and the subsequent ready formation of a five-membered spiro ring was highlighted.…”

Unexpected Formation of a Spiro Acridine and Fused Ring System from the Reaction between an N-Acridinylmethyl-Substituted Thiourea and Bromoacetonitrile under Basic Conditions

“…Only a few heterocyclic compounds possessing the spiro ring structural unit actually incorporate the acridinyl moiety , despite the likely predisposition of acridine and its derivatives to form such structures. Structures incorporating the acridine moiety have shown marked mutagenic, antiviral, and antitumor − activities and are thus of prime interest for pharmaceutical applications. In our previous studies − a convenient synthesis of spiro acridine compounds was described.…”

The Effects of Substituents Introduced into 9-Aminoacridine on Frameshift Mutagenicity and DNA Binding Affinity

“…2-Chloro-9-phenoxyacridine (16). The crude compound 14 (1157 mg), in phosphorus oxychloride (20 ml), was heated slowly to 90°C for 15 min, cooled at room temperature for 10 min, and then refluxed for 2 h. The reaction solution was cooled on an ice bath, and then poured carefully into a mixture of 15N NH3 (200ml) and dichloromethane (200ml) with ice cooling.…”

“…The residue was developed on a silica gel column (30 x 750 mm) with dichloromethane. Fractions containing 16 were collected and evaporated to dryness. The crude 16 9-Amino-2-chloroacridine (5).…”

“…Fractions containing 16 were collected and evaporated to dryness. The crude 16 9-Amino-2-chloroacridine (5). Ammonium carbonate (75 mg) was added to compound 16 (158 mg, 0.5 mmol) in phenol (1 ml), and then the solution was heated at 1200C for 45 min.…”