The three-dimensional hydrogen-bonded framework structure in the 1:1 proton-transfer compound of the drug quinacrine with 5-sulfosalicylic acid

Smith, Graham & Wermuth, Urs D. (2008) The three-dimensional hydrogen-bonded framework structure in the 1:1 proton-transfer compound of the drug quinacrine with 5-sulfosalicylic acid. Acta Crystallographica. Section C: Crystal Structure Communications, C64(8), o428-o430.

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For the hydrated proton-transfer compound 6-chloro-9-{(4-diethylammonio-2-methylbutyl)amino]-2-methoxyacridinium 3-carboxylato-4-hydroxybenzenesulfonate dihydrate, C23H32ClN3O2+ . C7H4O6S21 . 2H2O, (I), the conformational features, specifically those of the extended side chain at the 9-position of the acridine parent, have been compared with those of quinacrinium dichloride dihydrate (the drug atabrine or mepacrine). Racemic compound (I) has a three-dimensional hydrogen-bonded framework structure similar to atabrine but also involves the water molecules and both the carboxylate and the sulfonate groups of the anion in structure extension. The comparable conformational features found in this uncommon derivative of quibacrine indicate that (I) has potential as a possible pharmaceutical substitute for atabrine.

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ID Code: 14097
Item Type: Journal Article
Refereed: Yes
Keywords: quinacrine, mepacrine, atabrin, crystal structure
DOI: 10.1107/S0108270108020313
ISSN: 0108-2701
Subjects: Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > PHYSICAL CHEMISTRY (INCL. STRUCTURAL) (030600) > Structural Chemistry and Spectroscopy (030606)
Divisions: Past > QUT Faculties & Divisions > Faculty of Science and Technology
Copyright Owner: Copyright 2008 IUCr
Copyright Statement: Reproduced in accordance with the copyright policy of the publisher.
Deposited On: 26 Nov 2008 00:00
Last Modified: 29 Feb 2012 13:50

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