Section1= Chembox Identifiers
Section2= Chembox Properties
Section3= Chembox Hazards
Acridine, C13H9N, is an
organic compoundand a nitrogen heterocycle. Acridine is also used to describe compounds containing the C13N tricycle.
Acridine is structurally related to
anthracenewith one of the central CH groups is replaced by nitrogen. Acridine, a colorless solid, was first isolated from coal tar. It is a raw material used for the production of dyes and some valuable drugs. Many acridines, such as proflavine, also have antisepticproperties. Acridine and related derivatives bind to DNA and RNA due to their abilities to intercalate. Acridine orange(3,6-dimethylaminoacridine) is a nucleic acid-selective metachromatic stain useful for cell cycle determination. Acridarsineis formally derived from acridine by replacing the nitrogenatom with one of arsenic, and acridophosphineby replacing it with one of phosphorus.
Acridine was first isolated in
1871by Carl Gräbeand Heinrich Caro.
Acridine occurs naturally in
coal tar. It is separated from coal tar by extracting with dilute sulfuric acid; addition of potassium dichromateto this solution precipitates acridine bichromate. The bichromate is decomposed using ammonia.
Many synthetic processes are known for the production of acridine and its derivatives. A. Bernthsen condensed
diphenylaminewith carboxylic acids, in the presence of zinc chloridein the Bernthsen acridine synthesis. With formic acidas the carboxylic acid the reaction yields acridine itself, and with the higher homologues the derivatives substituted at the meso carbon atom are generated.
Other older methods for the
organic synthesisof acridines include condensing diphenylaminewith chloroformin the presence of aluminium chloride, by passing the vapours of orthoaminodiphenylmethane over heated litharge, by heating salicylic aldehydewith anilineand zinc chlorideto 260 °C or by distilling acridone(9-position a carbonylgroup) over zincdust.
A general method for acridine synthesis is the cyclisation of "N"-
phenylanthranilic acidor 2-(phenylamino)benzoic acid with phosphoric acid.
A classic method for the synthesis of acridones is the
Acridine and its homologues are stable compounds of weakly basic character. Acridine has a
pKaof 5.6, which is similar to that of pyridine. It also shares properties with quinolinewhich is the single fused homologue. Acridine crystallizes in needles which melt at 110 °C. It is characterized by its irritating action on the skin, and by the blue fluorescenceshown by solutions of its salts.
Acridine combines readily with
alkyl iodides to form alkyl acridinium iodides, which are readily transformed by the action of alkaline potassium ferricyanideto "N"-alkyl acridones. On oxidation with potassium permanganateit yields acridinic acidC9H5N(COOH)2 or quinoline-1,2-dicarboxylic acid. Acridine is easily oxidized by peroxymonosulfuric acidto the acridine amine oxide. The carbon 9-position of acridine is activated for addition reactions. The compound is reduced to the 9,10-dehydroacridine and reaction with potassium cyanidegives the 9-cyano-9,10-dehydro derivative.
Numerous derivatives of acridine are known and may be prepared by methods analogous to those used for the formation of the parent base.
9-Phenylacridineis the parent base of chrysanilineor 3,6-diamino-9-phenylacridine, which is the chief constituent of the dyestuff phosphine (not to be confused with phosphinegas), a by-product in the manufacture of rosaniline.
Chrysaniline forms red-coloured salts, which dye
silkand woola fine yellow; and the solutions of the salts are characterized by their fine yellowish-green fluorescence. Chrysaniline was synthesized by O. Fischer and G. Koerner by condensing ortho-nitrobenzaldehyde with aniline, the resulting ortho-nitro-para-diamino-triphenylmethane being reduced to the corresponding orthoamino compound, which on oxidation yields chrysaniline. Benzoflavin, an isomer of chrysaniline, is also a dye-stuff, and has been prepared by K. Oehler from meta-phenylenediamine and benzaldehyde. These substances condense to form tetra-aminotriphenylmethane, which, on heating with acids, loses ammonia and yields 3,6-diamino-9,10-dihydrophenylacridine, from which benzoflavin is obtained by oxidation. It is a yellow powder, soluble in hot water.
Acridine is a known human
carcinogen.Fact|date=May 2008 It causes mutations in incorporating into the DNA, and doing so creating an additional base on the opposite strand. If that mutation occurs in a coding sequence, it almost always leads to inactivation of the proteinit encoded.
* "Synthesis of Acridine-based DNA Bis-intercalating" Agents Gerard P. Moloney, David P. Kelly, P. Mack Molecules 2001, 6, 230-243 [http://www.mdpi.org/molecules/papers/60300230.pdf]
* Synthesis of acridone in "
Organic Syntheses" 19:6; "Coll. Vol." 2:15 [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv2p0015] from o-chlorobenzoic acid and aniline in a Goldberg reaction.
* Synthesis of 9-aminoacridine in "
Organic Syntheses" 22:5; "Coll. Vol." 3:53. [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv3p0053] from N-phenylanthranilic acid.
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