Structural studies on bioactive compounds. Part 26. Hydrogen bonding in the crystal structure of the N-methylformamide solvate of the immunomodulatory agent 2-amino-5-bromo-6-phenylpyrimidin-4-one (bropirimine): implications for the design of novel anti-tumour strategies.
The immunomodulatory agent bropirimine crystallizes from N-methylformamide (NMF) as a triply hydrogen-bonded duplex in the manner of a Watson-Crick guanine:cytosine base pair. The stoichiometry of the solvate is bropirimine:NMF (2:1) and all NMF molecules are in the Z-rotomeric form. The intermolecular hydrogen bonding is disrupted when the solvate is dissolved in deuteriated dimethyl sulphoxide at 37 degrees C. Bropirimine and other molecules which possess the 2-aminopyrimidin-4-one fragment are potentially capable of recognizing guanine or cytosine residues in single-stranded RNA or DNA by Watson-Crick bonding or double-stranded DNA by Hoogsteen bonds. The immunomodulatory properties of these compounds might be triggered by these encounters.
Stevens
M F
MF
Cancer Research Laboratories, University of Nottingham, UK.
Schwalbe
C H
CH
Patel
N
N
Gate
E N
EN
Bryant
P K
PK
D000276:Adjuvants, Immunologic / Q000737:chemistry* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D003596:Cytosine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D015195:Drug Design; D005559:Formamides / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012997:Solvents
D000276:Adjuvants, Immunologic; D005559:Formamides; D012997:Solvents; D003596:Cytosine; C033560:bropirimine; C002950:methylformamide