Acridine


Acridine

Chembox new
ImageFile=Acridine_chemical_structure.pngImageSize=250px
IUPACName=Acridine
OtherNames=
Section1= Chembox Identifiers
CASNo=260-94-6
PubChem=9215
SMILES=C1=CC=C2C(=C1)C=C3C=CC=CC3=N2

Section2= Chembox Properties
C=13|H=9|N=1
Appearance=
Density=
MeltingPt=107 °C
BoilingPt=346 °C
Solubility=

Section3= Chembox Hazards
MainHazards=
FlashPt=
Autoignition=

Acridine, C13H9N, is an organic compound and a nitrogen heterocycle. Acridine is also used to describe compounds containing the C13N tricycle.

Acridine is structurally related to anthracene with 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 antiseptic properties. 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. Acridarsine is formally derived from acridine by replacing the nitrogen atom with one of arsenic, and acridophosphine by replacing it with one of phosphorus.

History

Acridine was first isolated in 1871 by Carl Gräbe and Heinrich Caro.

Sources

Acridine occurs naturally in coal tar. It is separated from coal tar by extracting with dilute sulfuric acid; addition of potassium dichromate to 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 diphenylamine with carboxylic acids, in the presence of zinc chloride in the Bernthsen acridine synthesis. With formic acid as 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 synthesis of acridines include condensing diphenylamine with chloroform in the presence of aluminium chloride, by passing the vapours of orthoaminodiphenylmethane over heated litharge, by heating salicylic aldehyde with aniline and zinc chloride to 260 °C or by distilling acridone (9-position a carbonyl group) over zinc dust.

A general method for acridine synthesis is the cyclisation of "N"-phenylanthranilic acid or 2-(phenylamino)benzoic acid with phosphoric acid.

A classic method for the synthesis of acridones is the Lehmstedt-Tanasescu reaction.

Physical properties

Acridine and its homologues are stable compounds of weakly basic character. Acridine has a pKa of 5.6, which is similar to that of pyridine. It also shares properties with quinoline which 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 fluorescence shown by solutions of its salts.

Chemical properties

Acridine combines readily with alkyl iodides to form alkyl acridinium iodides, which are readily transformed by the action of alkaline potassium ferricyanide to "N"-alkyl acridones. On oxidation with potassium permanganate it yields acridinic acid C9H5N(COOH)2 or quinoline-1,2-dicarboxylic acid. Acridine is easily oxidized by peroxymonosulfuric acid to 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 cyanide gives 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-Phenylacridine is the parent base of chrysaniline or 3,6-diamino-9-phenylacridine, which is the chief constituent of the dyestuff phosphine (not to be confused with phosphine gas), a by-product in the manufacture of rosaniline.

Chrysaniline forms red-coloured salts, which dye silk and wool a 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.

Cancer link

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 protein it encoded.

References

* "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] open source
*

External links

* 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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Look at other dictionaries:

  • Acridine — Structure de l acridine Général Nom IUPAC Acridine …   Wikipédia en Français

  • acridine — ● acridine nom féminin (latin acrido, inis, odeur piquante) Composé C13H9N, faiblement basique, base de la fabrication de colorants. (L acridine est utilisée comme mutagène expérimental en analyse génétique.) Composé qui dérive de l acridine par… …   Encyclopédie Universelle

  • acridine — [ak′rə dēn΄, ak′rədin] n. [ ACRID + INE3] a colorless, crystalline, cyclic compound, C13H9N, found in coal tar: used to make dyes, of which some are used as antiseptics …   English World dictionary

  • acridine — akridinas statusas T sritis chemija formulė C₆H₄(CH)(N)C₆H₄ atitikmenys: angl. acridine rus. акридин …   Chemijos terminų aiškinamasis žodynas

  • acridine — n. a colourless crystalline compound used in the manufacture of dyes and drugs. Etymology: ACRID + INE(4) * * * acridine Chem. (ˈækrɪdaɪn) [? f. acrid a. + ine = Gr. ινη daughter, derivative.] A crystalline substance, C12H9N, of the diphenyl… …   Useful english dictionary

  • acridine — noun Date: circa 1877 a colorless crystalline compound C13H9N occurring in coal tar and important as the parent compound of dyes and pharmaceuticals …   New Collegiate Dictionary

  • acridine — /ak ri deen , din/, n. Chem. a colorless, crystalline solid, C13H9N, usually obtained from the anthracine fraction of coal tar: used chiefly in the synthesis of dyes and drugs. [1875 80; ACRID + INE2] * * * …   Universalium

  • acridine — noun a) A tricyclic aromatic heterocycle, dibenzopyridine, obtained from coal tar; it is used in the manufacture of dyes and drugs b) Any of many derivatives of this compound …   Wiktionary

  • acridine — 10 Azaanthracene; a dye, dye intermediate, and antiseptic precursor (9 aminoacridine, acriflavine, proflavine hemisulfate) derived from coal tar and irritating to skin and mucous membranes. SYN: dibenzopyridine. tetramethyl a. SYN: a. orange …   Medical dictionary

  • acridine — (entrée créée par le supplément) (a kri di n ) s. f. Terme de chimie. Base azotée (C12 H9 Az) qu on trouve dans les huiles lourdes de goudron, qui irrite les membranes muqueuses, et, respirée, provoque des éternuments violents …   Dictionnaire de la Langue Française d'Émile Littré


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