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An efficient route to xanthine based A(2A) adenosine receptor antagonists and functional derivatives. 2010

Paul Labeaume, and Ma Dong, and Michail Sitkovsky, and Elizabeth V Jones, and Rhiannon Thomas, and Sara Sadler, and Amy E Kallmerten, and Graham B Jones
Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA 02115, USA.

A one-pot route to 8-substituted xanthines has been developed from 5,6-diaminouracils and carboxaldehydes. Yields are good and the process applicable to a range of substrates including a family of A(2A) adenosine receptor antagonists. A new route to the KW-6002 family of antagonists is presented including a pro-drug variant, and application to related image contrast agents developed.

UI MeSH Term Description Entries
D011355 Prodrugs A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug. Drug Precursor,Drug Precursors,Pro-Drug,Prodrug,Pro-Drugs,Precursor, Drug,Precursors, Drug,Pro Drug,Pro Drugs
D011687 Purines A series of heterocyclic compounds that are variously substituted in nature and are known also as purine bases. They include ADENINE and GUANINE, constituents of nucleic acids, as well as many alkaloids such as CAFFEINE and THEOPHYLLINE. Uric acid is the metabolic end product of purine metabolism.
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D043705 Receptor, Adenosine A2A A subclass of adenosine A2 receptors found in LEUKOCYTES, the SPLEEN, the THYMUS and a variety of other tissues. It is generally considered to be a receptor for ADENOSINE that couples to the GS, STIMULATORY G-PROTEIN. Adenosine A2A Receptor,Adenosine A(2A) Receptor,Adenosine A2A Receptors,A2A Receptor, Adenosine,A2A Receptors, Adenosine,Receptors, Adenosine A2A
D058917 Adenosine A2 Receptor Antagonists Compounds that selectively bind to and block the activation of ADENOSINE A2 RECEPTORS. Adenosine A2A Receptor Antagonists,Adenosine A2B Receptor Antagonists
D019820 Xanthine A purine base found in most body tissues and fluids, certain plants, and some urinary calculi. It is an intermediate in the degradation of adenosine monophosphate to uric acid, being formed by oxidation of hypoxanthine. The methylated xanthine compounds caffeine, theobromine, and theophylline and their derivatives are used in medicine for their bronchodilator effects. (Dorland, 28th ed)

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