49
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of Double Headed Imidazoline Acyclo C-Nucleosides: 1,4-bis[1-Amino-5-oxo-4-Substituted-(Imidazolin-2-yl)]galacto-tetritols

Pages 349-357 | Received 08 Oct 2002, Accepted 27 Jan 2003, Published online: 07 Feb 2007

References

  • Remy , R.J. and Secrist , J.A. III . 1985 . Acyclic nucleosides other than acyclovir as potential antiviral agents . Nucleosides Nucleotides , 4 ( 3 ) : 411 – 427 .
  • Chu , C.K. and Cutler , S.J. 1986 . Chemistry and antiviral activities of acyclonucleosides . J. Heterocycl. Chem. , 23 : 289 – 319 .
  • Shaban , M.A.E. and Nasr , A.Z. 1997 . The chemistry of C-Nucleosides and their analogs I: C-Nucleosides of hetero monocyclic bases . Adv. Heterocycl. Chem. , 68 : 223 – 432 .
  • El Ashry , E.S.H. and El Kilany , Y. 1996 . Acyclonucleosides: Part 1. Seco-nucleosides . Adv. Heterocycl. Chem. , 67 : 391 – 438 .
  • El Ashry , E.S.H. and El Kilany , Y. 1997 . Acyclonucleosides: Part 2. Diseco-nucleosides . Adv. Heterocycl. Chem. , 68 : 1 – 64 .
  • El Ashry , E.S.H. and El Kilany , Y. 1998 . Acyclonucleosides: Part 3. Tri-,tetra-, and pentaseco-nucleosides . Adv. Heterocycl. Chem. , 69 : 129 – 215 .
  • Yasuzawa , T. , Yoshida , M. , Ichimura , M. , Shirahata , K. and Sano , H. 1987 . CV-1, A new antibiotic produced by a strain of streptomyces sp.II. Structure determination . J. Antibiot. , 40 ( 6 ) : 727 – 731 .
  • Gobin , S.J.P. and Phillips , J.A. 1991 . Immunosuppressive effect of 2-acetyl-4-tetrahydroxybutylimidazole (THI) in the rat . Clin. Exp. Immunol. , 85 ( 2 ) : 335 – 340 . Chem. Abstr., 1991, 115, 206449e
  • Iscaro , A. , Mackay , I.R. and O'Brien , C. 1988 . Lymphopenic effects on mice of component of ammonia caramel, 2-acetyl-4(5)-tetrahydroxy-butylimidazole (THI) . Immunol. Cell. Biol. , 66 ( 5&6 ) : 395 – 402 . Chem. Abstr. 1989, 111, 38125t
  • Mandel , T.E. , Koulamanda , M. and Mackay , I.R. 1992 . Prevention of spontaneous and cyclophosphamide-induced diabetes in non-obese diabetic (NOD) mice with oral 2-acetyl-4-tetrahydroxybutylimidazole (THI), a component of caramel coloring III . Clin. Exp. Immunol. , 88 ( 3 ) : 414 – 419 . Chem. Abstr. 1992, 117, 62594q
  • Rohrle , A.N. and Schmidhammer , H. 1998 . Synthesas of 1-(1H-Imidazol-2-yl)ethane-1,2-diol derivatives: A novel class of protein kinase C inhibitors . Helv. Chim. Acta , 81 : 1070 – 1076 .
  • Kudzma , L.V. and Turnbull , S.P. 1991 . Expedient synthesis of 4(5)-[1,(2,3-dimethylphenyl)-1H-imidazole, The α2-adrenergic agonist medetomidine . Synthesis , : 1021 – 1022 .
  • Sun , Z.-Y. , Kwon , C.-H, and Wurpel , J.N.D. 1994 . Structure- activity study of 5-substituted 1-carbobenzoxy-2-iminohydantoins a potential anticonvulsant agents . J. Med. Chem. , 37 : 2841 – 2845 .
  • Kramer , K. , Elz , S. , Pertz , H.H. and Schunack , W. 1998 . Na-Alkylated derivatives of 2-phenylhistamines: Synthesis and in vitro activity of potent histamine H1-receptor agonists . Bioorg. Med. Chem. Lett. , 8 ( 18 ) : 2583 – 2588 . Chem. Abstr. 1999, 130, 3801a
  • Timmerman , H. and Vander Goot , H. Preparation of Imidazolyl-alkylisothioureas and Related Compounds as Histamine H3 Receptor Agonists or Antagnists . US Patent 5,837,718 . Nov 17, 1998 . Chem. Abstr. 1999, 130, 13989g
  • Adams , J.L. , Lee , Di and Long , S.A. Preparation of Pyrimidinylimidazoles as CSBP/PK/p38 Kinase Inhibitors . PCT Int. Appl. WO 9,857,966 . Dec 23, 1998 . Chem. Abstr. 1999, 130, 66512c
  • Bhide , R.S. , Ding , C.Z. , Hunt , J.T. , Kim , S.-H. and Leftheris , K. Preparation of Imidazole Containing Quinoline and Benzazepine Derivatives as Inhibitors of Farnesyl Protein Transferase . PCT Int. Appl. WO 9,901,434 . Jan 14, 1999 . Chem. Abstr. 1999, 130, 125071b
  • Elokdah , H. , Sulkowski , T.S. and Strike , D.P. Preparation of 2-(Substituted Sulfanyl)-3,5-dihydro-imidazol-4-ones for Increasing HDL Blood Levels . US Patant 5,877,324 . Mar 2, 1999 . Chem. Abstr. 1999, 130, 196654m
  • Andreani , A. , Locatelli , A. and Rambaldi , M. 1995 . Synthesis and herbicidal properties of 3-(2-oxo-1-imidazolidinyl-iminomethyl)indoles . J. Heterocycl. Chem. , 32 : 49 – 51 .
  • Hagiwara , K. , Iihama , T. , Marumo , S. , Sano , S. and Shimoda , S. Preperation of 2-(2-Pyridyl)imidazole Compounds as Agricultural Fungicides . Jpn Kokai Patant 97/85,879 . Dec 8, 1998 . Chem. Abstr. 1999, 130, 66497b
  • Assmann , L. , Stenzel , K. , Erdelen , C. and Kugler , M. Preparation of Nitrophenylsulfonylimidazoles as Fungicides and Pesticides . Ger Patant Offen DE 19,829,740 . Jan 28, 1999 . Chem. Abstr. 1999, 130, 125074m
  • Shaban , M.A.E. , Nasr , A.Z. and Taha , M.A.M. 1995 . Synthesis of 1,3,4-thiadiazole and 1,2,4-triazole acyclo C-nucleosides . J. Carbohydr. Chem. , 14 ( 7 ) : 985 – 994 .
  • Shaban , M.A.E. , Nasr , A.Z. and Taha , M.A.M. 1995 . Synthesis of acyclo C-nucleosides: 6-(D-Gluco-pentitol-1-yl)-1,2,4-triazolo[3,4-b]1,3,4-thiadiazoles and 1,4-Bis(1,2, 4-triazolo[3,4-b]1,3,4-thiadiazol-6-yl) galacto-tetritols . Pharmazie , 50 : 534 – 537 .
  • Nasr , A.Z. 1996 . Synthesis of 1,2,4-triazole and imidazole acyclo C-nucleosides . Alex. J. Pharm. Sci. , 10 ( 2 ) : 139 – 141 . Chem. Abstr. 1996, 125 301457w
  • Shaban , M.A.E. , Nasr , A.Z. and Morgaan , A.E.A. 2000 . Synthesis and antimicrobial activity of acyclo C-nucleoside: 3-(alditol-1-yl)-7-oxo-5-phenyl-1,2,4-triazolo [4,3-a]pyrimidines . Pharmazie , 55 : 87 – 93 .
  • Lewis , B.A. , Smith , F. and Stephen , A.M. 1963 . Aldric acids. (13) Galactaric acid and its derivatives . Methods Carbohydr. Chem. , 2 : 38 – 46 .
  • Camparini , A. , Celli , A.M. , Ponticelli , F. and Tedeschi , P. 1978 . Synthesis and structure of dihydro-1,2,4-triazin-6(1H)-ones (1) . J. Heterocycl. Chem. , 15 : 1271 – 1276 .
  • Leschinsky , K.L. and Chupp , J.P. 1980 . Heterocycles from substituted amides. IX. 4,5-Dihydro-1,2,4-triazin-6-(1H)-ones from 2-isocyanoacetates and hydrazines . J. Heterocycl. Chem. , 17 : 1621 – 1622 .
  • Rao , T.S. and Revankar , G.R. 1995 . Synthesis of certain acyclic nucleoside analogs of 1,2,4-triazolo[3,4-f][1,2,4]triazine and pyrimido[5,4-d]pyrimidine . Nucleosides Nucleotides , 14 ( 7 ) : 1601 – 1612 .
  • Townsend , L.B. and Robins , R.K. 1969 . The mass spedra of formycin B and showdomycin. Carbon linked nucleoside antibiotic (1) . J. Heterocycl. Chem. , 6 : 459 – 464 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.