Synthesis of an o-Nitrobenzyl Attached A₁ Adenosine Receptor Antagonist, a Prodrug Approach

References

• Daly , J.W. 1982 . Adenosine receptors: targets for future drugs . J. Med. Chem. , 25 : 197 – 207 .
   PubMed Web of Science ®Google Scholar
• Jacobson , K.A. , Van Galen , P.J.M. and Williams , M. 1992 . Adenosine receptors: pharmacology, structure-activity relationships, and therapeutic potential . J. Med. Chem. , 35 : 407 – 422 .
   PubMed Web of Science ®Google Scholar
• Shimada , J. , Suzuki , F. , Nonaka , H. and Ishii , A. 1992 . 8-Polycycloalkyl-1,3-dipropylxanthines as potent and selective antagonists for A1-adenosine receptors . J. Med. Chem. , 35 : 924 – 930 .
   PubMed Web of Science ®Google Scholar
• Jacobson , K.A. , Kiriasis , L. , Barone , S. , Bradbury , B.J. , Kammula , U. , Campagne , J.M. , Secunda , S. , Daly , J.W. , Neumeyer , J.L. and Pfleiderer , W. 1989 . Sulfur-containing 1,3-dialkylxanthine derivatives as selective antagonists at A1-adenosine receptors . J. Med. Chem. , 32 : 1873 – 1879 .
   PubMed Web of Science ®Google Scholar
• Daly , J.W. , Padgett , W. , Shamim , M.T. , Butts-Lamb , P. and Waters , J. 1985 . 1,3-Dialkyl-8-(p-sulfophenyl)xanthines: potent water-soluble antagonists for A1- and A2-adenosine receptors . J. Med. Chem. , 28 : 487 – 492 .
   PubMed Web of Science ®Google Scholar
• Shamim , M.T. , Ukena , D. , Padgett , W.L. and Daly , J.W. 1989 . Effects of 8-phenyl and 8-cycloalkyl substituents on the activity of mono-, di-, and trisubstituted alkylxanthines with substitution at 1-, 3-, and 7-positions . J. Med. Chem. , 32 : 1231 – 1237 .
   PubMedGoogle Scholar
• Kim , H.O. , Ji , X.D. , Melman , N. , Olah , M.E. , Stiles , G.L. and Jacobson , K.A. 1994 . Structure-activity relationships of 1,3-dialkylxanthine derivatives at rat A3 adenosine receptors . J. Med. Chem. , 37 : 3373 – 3382 .
   Google Scholar
• Jacobson , K.A. , Shi , D. , Gallo-Rodriguez , C. , Manning , M. Jr. , Mueller , C. , Daly , J.W. , Neumeyer , J.L. , Kiriasis , L. and Pfleiderer , W. 1993 . Effects of trifluoromethyl and other substituents on activity of xanthines at adenosine receptors . J. Med. Chem. , 36 : 2639 – 2644 .
   Google Scholar
• Scammells , P.J. , Baker , S.P. , Bellardinelli , L. , Olsson , R.A. , Russell , R.A. and Wright , M.J. 1996 . The synthesis of the novel adenosine agonists, exo- and endo-N6-(5,6-epoxynorborn-2-yl)adenosine . Tetrahedron , 52 : 4735 – 4744 .
   Google Scholar
• Scammells , P.J. , Baker , S. , Olsson , R. and Bellardinelli , L. A1 Adenosine Receptor Agonists and Antagonists as Diuretics . US Patent 5,446,046 . August 29, 1995 .
   Google Scholar
• Kalbag , S.M. and Roeske , R.W. 1975 . A photolabile protecting group for histidine . J. Am. Chem. Soc. , 97 : 440
   Google Scholar
• Perri , S.T. , Slater , S.C. , Toske , S.G. and White , J.D. 1990 . Tandem photochemical synthesis of N-amino β-lactams from pyrazolidine-3-ones . J. Org. Chem. , 55 : 6037 – 6047 .
   Web of Science ®Google Scholar
• Patchornik , A. , Amit , B. and Woodward , R.B. 1970 . Photosensitive protecting groups . J. Am. Chem. Soc. , 92 : 6333 – 6335 .
   Web of Science ®Google Scholar
• Miknis , G.F. and Williams , R.M. 1993 . Total synthesis of (±)-aspirochlorine . J. Am. Chem. Soc. , 115 : 536 – 547 .
   Google Scholar
• Mueller , C.E. , Sauer , R. , Maurinsh , Y. , Huertas , R. , Fuelle , F. , Klotz , K-N. , Nagel , J. and Hauber , W. 1998 . A2A-Selective adenosine receptor antagonists: development of water-soluble prodrugs and a new tritiated radioligand . Drug Dev. Res. , 45 : 190 – 197 .
   Google Scholar
• Sauer , R. , Maurinsh , J. , Reith , U. , Fuelle , F. , Klotz , K-N. and Mueller , C.E. 2000 . Water-soluble phosphate products of 1-propargyl-8-styrylxanthine derivatives, A2a-selective adenosine receptor antagonists . J. Med. Chem. , 43 : 440 – 448 .
   PubMed Web of Science ®Google Scholar
• Kyowa Hakko Kogyo Co., Ltd. Xanthine Compounds . US Patent 5,525,607 . June 11, 1996 .
   Google Scholar
• Papesch , V. and Schroeder , E.F. 1951 . Synthesis of 1-mono- and 1,3-di-substituted 6-aminouracils. Diuretic activity . J. Org. Chem. , 16 : 1879 – 1890 .
   Web of Science ®Google Scholar
• Speer , J.H. and Raymond , A.L. 1953 . Some alkyl homologs of theophylline . J. Am. Chem. Soc. , 75 : 114 – 115 .
   Google Scholar
• Blicke , F.F. and Godt , H.C. 1954 . Reactions of 1,3-dimethyl-5,6-diaminouracil . J. Am. Chem. Soc. , 76 : 2798 – 2800 .
   Web of Science ®Google Scholar
• Chang , H.X. , Zhou , L. , McCargar , R.D. , Mahmud , T. and Hirst , I. 1999 . A convenient practical method for the preparation of (−)-(1S,2S)-5-norbornene-2-carboxylic acid, incorporation efficient recovery of the chiral auxiliary d-pantolactone . Org. Process Res. Dev. , 3 : 289 – 291 .
   Google Scholar