Synthesis of Homologated Halovinyl Derivatives from Aristeromycin and Their Inhibition of Human Placental S-Adenosyl-L-homocysteine HydrolaseFootnote¶

This paper is dedicated to the late Professor T. Hata.

References

• Lewandowska , E. , Neschadimenko , V. , Wnuk , S. F. and Robins , M. J. 1997 . Tetrahedron , 53 : 6295 – 6302 .
   Google Scholar
• Ueland , P. M. 1982 . Pharmacol. Rev. , 34 : 223 – 253 .
   PubMed Web of Science ®Google Scholar
• Wolfe , M. S. and Borchardt , R. T. 1991 . J. Med. Chem. , 34 : 1521 – 152 .
   PubMed Web of Science ®Google Scholar
• Yuan , C.-S. , Liu , S. , Wnuk , S. F. , Robins , M. J. and Borchardt , R. T. 1996 . Advances in Antiviral Drug Design , Edited by: DeClercq , E. Vol. 2 , 41 – 88 . Greenwich : JAI Press .
   Google Scholar
• Keller , B. T. and Borchardt , R. T. 1988 . Antiviral Drug Development: A Multidisciplinary Approach , Edited by: DeClercq , E. and Walker , R. T. 123 – 138 . New York : Plenum .
   Google Scholar
• Cools , M. and De Clercq , E. 1989 . Biochem. Pharmacol. , 38 : 1061 – 1067 .
   PubMed Web of Science ®Google Scholar
• Wnuk , S. F. , Yuan , C.-S. , Borchardt , R. T. , Balzarini , J. , De Clercq , E. and Robins , M. J. 1994 . J. Med. Chem. , 37 : 3579 – 3587 .
   PubMed Web of Science ®Google Scholar
• McCarthy , J. R. , Jarvi , E. T. , Matthews , D. P. , Edwards , M. L. , Prakash , N. J. , Bowlin , T. L. , Mehdi , S. , Sunkara , P. S. and Bey , P. 1989 . J. Am. Chem. Soc. , 111 : 1127 – 1128 .
   Web of Science ®Google Scholar
• Jarvi , E. T. , Mc Carthy , J. R. , Mehdi , S. , Matthews , D. P. , Edwards , M. L. , Prakash , N. J. , Bowlin , T. L. , Sunkara , P. S. and Bey , P. 1991 . J. Med. Chem. , 34 : 647 – 656 .
   PubMed Web of Science ®Google Scholar
• Yuan , C.-S. , Yeh , J. , Liu , S. and Borchardt , R. T. 1993 . J. Biol. Chem. , 268 : 17030 – 17037 .
   PubMed Web of Science ®Google Scholar
• Liu , S. , Wnuk , S. F. , Yuan , C. , Robins , M. J. and Borchardt , R. T. 1993 . J. Med. Chem. , 36 : 883 – 887 .
   PubMed Web of Science ®Google Scholar
• Robins , M. J. and Wnuk , S. F. 1988 . Tetrahedron Lett. , 29 : 5729 – 5732 .
   Web of Science ®Google Scholar
• Robins , M. J. , Wnuk , S. F. , Mullah , K. B. , Dalley , N. K. , Borchardt , R. T. , Lee , Y. and Yuan , C.-S. 1993 . Nucleosides and Nucleotides as Antitumor and Antiviral Agents , Edited by: Chu , C. K. and Baker , D. C. 115 – 126 . New York : Plenum Press .
   Google Scholar
• Robins , M. J. , Wnuk , S. F. , Mullah , K. B. , Dalley , N. K. , Yuan , C.-S. , Lee , Y. and Borchardt , R. T. 1994 . J. Org. Chem. , 59 : 544 – 555 .
   Web of Science ®Google Scholar
• Wnuk , S. F. , Yuan , C.-S. , Borchardt , R. T. , Balzarini , J. , De Clercq , E. and Robins , M. J. 1997 . J. Med. Chem. , 40 : 1608 – 1618 .
   PubMed Web of Science ®Google Scholar
• Huang , H. , Yuan , C.-S. , Wnuk , S. F. , Robins , M. J. and Borchardt , R. T. Arch. Biochem. Biophys , in press
   Google Scholar
• Yuan , C.-S. , Liu , S. , Wnuk , S. F. , Robins , M. J. and Borchardt , R. T. 1994 . Biochemistry , 33 : 3758 – 376 .
   PubMed Web of Science ®Google Scholar
• Yuan , C.-S. , Wnuk , S. F. , Liu , S. , Robins , M. J. and Borchardt , R. T. 1994 . Biochemistry , 33 : 12305 – 12311 .
   PubMed Web of Science ®Google Scholar
• Wnuk , S. F. , Liu , S. , Yuan , C.-S. , Borchardt , R. T. and Robins , M. J. 1996 . J. Med. Chem. , 39 : 4162 – 4166 .
   PubMed Web of Science ®Google Scholar
• Parry , R. J. , Muscate , A. and Askonas , L. J. 1991 . Biochemistry , 30 : 9988 – 9997 .
   PubMed Web of Science ®Google Scholar
• Guranowski , A. , Montgomery , J. A. , Cantoni , G. L. and Chiang , P. K. 1981 . Biochemistry , 20 : 110 – 11 .
   PubMed Web of Science ®Google Scholar
• Borchardt , R. T. , Keller , B. T. and Patel-Thombre , U. 1984 . J. Biol. Chem. , 259 : 4353 – 4358 .
   PubMed Web of Science ®Google Scholar
• Borthwick , A. D. and Biggadike , K. 1992 . Tetrahedron , 48 : 571 – 62 .
   Web of Science ®Google Scholar
• Marquez , V. E. 1996 . Advances in Antiviral Drug Design , Edited by: DeClercq , E. Vol. 2 , 89 – 146 . Greenwich : JAI Press .
   Google Scholar
• Matthews , D. P. , Edwards , M. L. , Mehdi , S. , Koehl , J. R. , Wolos , J. A. and McCarthy , J. R. 1993 . Bioorg. Med. Chem. Lett. , 3 : 165 – 16 .
   Web of Science ®Google Scholar
• Liu , S. , Wolfe , M. S. , Yuan , C. , Ali , S. M. and Borchardt , R. T. 1992 . Bioorg. Med. Chem. Lett. , 2 : 1741 – 1744 .
   Web of Science ®Google Scholar
• Liu , S. , Yuan , C.-S. and Borchardt , R. T. 1996 . J. Med. Chem. , 39 : 2347 – 2353 .
   Google Scholar
• Jeong , L. S. , Marquez , V. E. , Yuan , C.-S. and Borchardt , R. T. 1995 . Heterocycles , 41 : 2651 – 2655 .
   Web of Science ®Google Scholar
• Jones , M. F. and Roberts , S. M. 1988 . J. Chem. Soc., Perkin Trans. , I : 2927 – 2932 .
   Google Scholar
• Shuto , S. , Obara , T. , Saito , Y. , Andrei , G. , Snoeck , R. , De Clercq , E. and Matsuda , A. 1996 . J. Med. Chem. , 39 : 2392 – 2399 .
   PubMedGoogle Scholar
• Wolfe , M. S. , Lee , Y. , Baitlett , W. J. , Borcherding , D. R. and Borchardt , R. T. 1992 . J. Med. Chem. , 35 : 1782 – 179 .
   PubMed Web of Science ®Google Scholar
• Shuto , S. , Obara , T. , Toriya , M. , Hosoya , M. , Snoeck , R. , Andrei , G. , Balzarini , J. and De Clercq , E. 1992 . J. Med. Chem. , 35 : 324 – 33 .
   PubMed Web of Science ®Google Scholar
• Obara , T. , Shuto , S. , Saito , Y. , Toriya , M. , Ogawa , K. , Yaginuma , S. , Shigeta , S. and Matsuda , A. 1996 . Nucleosides Nucleotides , 15 : 1157 – 1167 .
   Google Scholar
• Pfitzner , K. E. and Moffatt , J. G. 1965 . J. Am. Chem. Soc. , 87 : 5661 – 5670 .
   Web of Science ®Google Scholar
• Van Leusen , A. M. , Reith , B. A. , Iedema , A. J. W. and Strating , J. 1972 . Recl. Trav. Chim. Pays Bas , 91 : 37 – 49 .
   Google Scholar
• Bodenteich , M. , Marquez , V. E. , Hallows , W. H. and Goldstein , B. M. 1992 . J. Org. Chem. , 57 : 2071 – 2076 .
   Web of Science ®Google Scholar
• Watanabe , Y. , Ueno , Y. , Araki , T. , Endo , T. and Okawara , M. 1986 . Tetrahedron Lett. , 27 : 215 – 21 .
   Web of Science ®Google Scholar
• Wnuk , S. F. and Robins , M. J. 1993 . Can. J. Chem. , 71 : 192 – 198 .
   Web of Science ®Google Scholar
• Pereyre , M. , Quintard , J.-P. and Rahm , A. 1987 . Tin in Organic Synthesis , London : Butterworths .
   Google Scholar
• Tius , M. A. and Kawakami , J. K. 1993 . Synlett , : 207 – 208 .
   Google Scholar
• Meyer , W. , Böhnke , E. and Follmann , H. 1976 . Angew. Chem., Int. Ed. Engl. , 15 : 499 – 50 .
   PubMed Web of Science ®Google Scholar
• Meyer , W. and Follmann , H. 1980 . Chem. Ber. , 113 : 2530 – 254 .
   Google Scholar
• Hollmann , J. and Schlimme , E. 1984 . Liebigs Ann. Chem. , : 98 – 107 .
   Google Scholar
• Kim , I.-Y. , Zhang , C.-Y. , Cantoni , G. L. , Montgomery , J. A. and Chiang , P. K. 1985 . Biochim. Biophys. Acta , 829 : 150 – 155 .
   PubMedGoogle Scholar
• Marshall , J. A. , Andersen , N. H. and Schlicher , J. W. 1970 . J. Org. Chem. , 35 : 858 – 861 .
   Web of Science ®Google Scholar