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Synthesis and stability of 3-hydroxyanagrelide, a biologically potent metabolite of anagrelide

Lookup NU author(s): Dr Richard Scott, Kristin Downey, Dr Keith Healy, Dr Alistair Henderson, Claire Robinson, Emeritus Professor Bill Clegg, Dr Ross Harrington, Professor Bernard Golding

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Abstract

Metabolism of 6,7-dichloro-1,5-dihydroimidazo[2,1-b]quinazolin-2-one (anagrelide), a drug for treating essential thrombocythemia, gives 6,7-dichloro-3-hydroxy-1,5-dihydroimidazo[2,1-b]quinazolin-2-one (3-hydroxyanagrelide) and 2-amino-5,6-dichloro-3,4-dihydroquinazoline. To enable the properties of 3-hydroxyanagrelide to be fully evaluated, the racemic compound has been synthesized. In pH 7.4 aqueous buffer 3-hydroxyanagrelide readily equilibrates with an isomer, 6,7-dichloro-1-hydroxy-3,5-dihydroimidazo[1,2-alpha]-quinazolin-2-one,and is also hydrolyzed to 2-amino-5,6-dichloro-3,4-dihydroquinazoline. 3-Hydroxyanagrelide (half-life 40 hours) was the dominant species at equilibrium and it was concluded that the equilibration and decomposition are sufficiently slow that published assays of 3-hydroxyanagrelide are reliable.


Publication metadata

Author(s): Scott RB, Downey KM, Healy KP, Henderson AP, Robinson CL, Clegg W, Harrington RW, Franklin R, Golding BT

Publication type: Article

Publication status: Published

Journal: Heterocycles

Year: 2012

Volume: 86

Issue: 2

Pages: 1637-1646

Print publication date: 30/10/2012

ISSN (print): 0385-5414

ISSN (electronic): 1881-0942

Publisher: Japan Institute of Heterocyclic Chemistry

URL: http://dx.doi.org/10.3987/COM-12-S(N)115

DOI: 10.3987/COM-12-S(N)115


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