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Original Articles

An Efficient Route to Novel 4,5‐Di‐ and 2,4,5‐Tri Substituted Imidazoles from Imidazo[1,5‐a]‐1,3,5‐triazine (5,8‐Diaza‐7,9‐dideazapurine) Derivatives

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Pages 127-136 | Received 08 Aug 2003, Accepted 06 Oct 2003, Published online: 01 Jun 2007

References

  • Tafi , A. , Costi , R. , Botta , M. , Di Santo , R. , Corelli , F. , Massa , S. , Ciacci , A. , Manetti , F. and Artico , M. 2002 . Antifungal agents. 10. New derivatives of 1‐[(aryl)[4‐aryl‐1H‐pyrrol‐3‐yl]methyl]‐1H‐imidazole, synthesis, anti‐Candida activity, and quantitative structure–analysis relationship studies . J. Med. Chem. , 45 : 2720 – 2732 . [PUBMED] [INFOTRIEVE] [CSA]
  • De Esch , I. J.P. , Gaffar , A. , Menge , W. M.P.B. and Timmerman , H. 1999 . Synthesis and histamine H3 receptor activity of 4‐(n‐alkyl)‐1H‐imidazoles and 4‐(ω‐phenylalkyl)‐1H‐imidazole . Bioorg. Med. Chem. , 7 : 3003 – 3009 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Slee , D. H. , Romano , S. J. , Yu , J. , Nguyen , T. N. , John , J. K. , Raheja , N. K. , Axe , F. U. , Jones , T. K. and Ripka , W. C. 2001 . Development of potent non‐carbohydrate imidazole‐based small molecule selection inhibitors with anti‐inflammatory activity . J. Med. Chem. , 44 : 2094 – 2107 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
  • Bell , I. M. , Gallicchio , S. N. , Abrams , M. , Beshore , D. C. , Buser , C. A. , Culberson , J. C. , Davide , J. , Ellis‐Hutchings , M. , Fernandes , C. , Gibbs , J. B. , Graham , S. L. , Hartman , G. D. , Heimbrook , D. C. , Homnick , C. F. , Huff , J. R. , Kassahun , K. , Koblan , K. S. , Kohl , N. E. , Lobell , R. B. , Lynch , J. J. Jr. , Miller , P. A. , Omer , C. A. , Rodrigues , A. D. , Walsh , E. S. and Williams , T. M. 2001 . Design and biological activity of (S)‐4‐(5‐{[1‐(3‐chlorobenzyl)‐2‐oxopyrrolidin‐3‐ylamino]methyl}imidazol‐1‐ylmethyl)benzonitrile, a 3‐aminopyrrolidinone farnesyltransferase inhibitor with excellent cell potency . J. Med. Chem. , 44 : 2933 – 2949 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
  • Golankiewicz , B. , Holtwick , J. B. , Holmes , B. N. , Duesler , E. N. and Leonard , N. J. 1979 . Synthesis of imidazo[1,5‐a]‐1,3,5‐triazinones by cyclization‐rearrangement . J. Org. Chem. , 44 : 1740 – 1742 .
  • Holtwick , J. B. , Golankiewicz , B. , Holmes , B. N. and Leonard , N. J. 1979 . Guanine, hypoxanthine and xanthine analogues. Synthesis of imidazo[1,5‐a]‐1,3,5‐triazinones via rearrangement . J. Org. Chem. , 44 : 3835 – 3839 .
  • Golankiewicz , B. , Zeidler , J. and De Clercq , E. 1987 . Synthesis and biological activity of C‐acyclic nucleosides of imidazo[1,5‐a]‐1,3,5‐triazines . Nucleosides Nucleotides , 6 : 663 – 678 .
  • Golankiewicz , B. , Januszczyk , P. , Ikeda , S. , Balzarini , J. and De Clercq , E. 1995 . Synthesis and antiviral activity of benzyl‐substituted imidazo[1,5‐a]‐1,3,5‐triazine (5,8‐diaza‐7,9‐dideazapurine) derivatives . J. Med. Chem. , 38 : 3558 – 3565 . [PUBMED] [INFOTRIEVE] [CSA]
  • Bourn , A. J.R. , Gillies , D. G. and Randall , E. W. 1964 . Cis‐trans isomerism in formanilide . Tetrahedron , 20 : 1811 – 1818 . and references therein[CROSSREF]
  • Barbarella , G. , Tugnoli , V. and Zambianchi , M. 1991 . Imidazole ring opening of 7‐methylguanosine at physiological pH . Nucleosides Nucleotides , 10 : 1759 – 1769 . and references therein
  • Fujii , T. , Sato , T. , Itaya , T. and Purines , V. 1971 . The Dimroth rearrangement of 1‐alkoxyadenines: The synthesis of N‐alkoxyadenines . Chem. Pharm. Bull. , 19 : 1731 – 1734 .
  • Fujii , T. , Saito , T. and Kawanishi , M. 1978 . A general synthetic route to 3,9‐dialkyladenines and their ring opening . Tetrahedron Lett. , 50 : 5007 – 5010 . [CROSSREF]
  • Golankiewicz , B. , Zeidler , J. and Popenda , M. 1990 . Determination of the tautomerism of 5,5‐disubstituted analogues of 6‐amino‐2‐thiouracil by 1H and 13C nuclear magnetic resonance spectroscopy . J. Chem. Soc., Perkin Trans. 2 , : 1001 – 1004 . [CROSSREF]

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