9-Aminoacridine salts

Table 9 Repository antimalarial properties of 4 aminoquinoline and 9-aminoacridine salts against P. berghei in mice [36,145]...

Primary halides are more reactive than secondary compounds quaternary salt formation does not occur with tertiary halides, elimination always occurring to give the hydriodide and an olefln, Also, the larger the alkyl group the slower is the reaction this is shown by the very slow reaction of dodecyl bromide with quinoline, and even butyl iodide is much slower to react than methyl iodide. The longer chain primary halides commonly undergo elimination rather than cause quaternization for example, n-octyl and cetyl iodides give only the hydriodides when heated with 9-aminoacridine. ... 

W. S. Chow and J. Barber, Salt dependent changes of 9-aminoacridine as a measure of charge-densities of membrane surfaces, J. Biochem. Biophys. Methods 3, 173-185 (1980). 

Pyridinium or diisoquinolinium salts, such as (36) and (37), have been used as topical antifungals (60BRP839505, 33FRP738028), whilst acranil (38), an antiprotozoal based on an aminoacridine, possesses general antiviral activity (73MI20900). 

The antifungal activity of a series of salts of 9-aminoacridine and its derivatives was shown to correlate with the length of the carbon chain of the anion. The effect is thought to be related to increased lipid solubility and ion pair formation. ... 

Ogawa, H.L, Tsumta, S., and Niyitani, Y., Mutagenicity of metal salts in combination with 9-aminoacridine in Salmonella typhimurium. Jpn. J. Genetics, 62, 159-162, 1987. 

Although phenyl azide can be prepared from phenyl hydrazine hydrochloride by addition of NaNO and HCl, we have used two other methods exclusively. If the ring contains a deactivating heteroatom, a direct nucleophilic substitution of a halogen by Njj in a suitable solvent is usually successful. If the ring is homoannular, then generation of the diazonium salt from nitrous acid, followed by substitution with Nh, produces the azide. For example, 9-azidoacridine can be prepared from 9-chloroacridine, and 3-azidoacridine is prepared from 3-aminoacridine. ... 

On deprotonation, 1-arylindazolium salts form l-arylindazol-3-ylidenes which rearrange spontaneously via ring cleavage, ring closure and proton transfer to 9-aminoacridines (Scheme 45). ... 

Borane pyridine complex 550 Organic Salts and Solutions 9-Aminoacridine hydrochloride Benzethonium chloride... 

It is important to note the favorable influence of protonation (iminium formation) on the ease of reduction. The salt form is expected to be present in vivo, similar to other aminoacridines . Although the potentials are fairly negative under our conditions, we believe that they may be appreciably more positive in vivo due to stereochemical effects. 

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