Crystal structures of azathioprine dihydrate and 6-methylmercaptopurine trihydrate.

Abstract:

:The crystal and molecular structures of 6-methylmercaptopurine trihydrate and of azathioprine dihydrate were determined by the use of three-dimensional, X-ray, diffractometer data and were refined by least squares. Both molecules crystallize in the N(9)-H tautomer form, in contrast to the N(7)-H tautomer form found in crystals of 6-mercaptopurine. Unlike 6-mercaptopurine, or other thiopurines that have unsubstituted thio groups, the sulfur atoms of 6-methylmercaptopurine and azathioprine do not act as hydrogen-bond acceptors in the crystal structures. These two derivatives of 6-mercaptopurine assume a conformation in which the substituents on the sulfur atom are directed away from the imidazole moiety of the purine.

journal_name

J Pharm Sci

authors

Cook WJ,Bugg CE

doi

10.1002/jps.2600640206

subject

Has Abstract

pub_date

1975-02-01 00:00:00

pages

221-25

issue

2

eissn

0022-3549

issn

1520-6017

pii

S0022-3549(15)40065-6

journal_volume

64

pub_type

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