Literature DB >> 11527718

Synthesis and purine receptor affinity of 6-oxopurine nucleosides and nucleotides containing (N)-methanocarba-pseudoribose rings.

G Ravi1, K Lee, X Ji, H S Kim, K A Soltysiak, V E Marquez, K A Jacobson.   

Abstract

6-Oxopurine derivatives containing a northern (N) methanocarba modification (i.e., fused cyclopropane and cyclopentane rings in place of the ribose) were synthesized and the adenosine receptor affinity measured. Guanine or hypoxanthine was coupled at the 7-position, or 1,3-dibutylxanthine was coupled at the 9-position. The pseudoribose ring was also substituted at the 5'-position with an N-methyluronamide or with phosphate groups.

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Year:  2001        PMID： 11527718      PMCID： PMC4955390          DOI： 10.1016/s0960-894x(01)00450-4

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  15 in total

1.  Rapid up-regulation of P2Y messengers during granulocytic differentiation of HL-60 cells.

Authors:  D Communi; R Janssens; B Robaye; N Zeelis; J M Boeynaems
Journal:  FEBS Lett       Date:  2000-06-09       Impact factor: 4.124

2.  GTP analogue hydrolysis by the Gs protein: implication for the role of catalytic glutamine in the GTPase reaction.

Authors:  T Zor; R Andorn; I Sofer; M Chorev; Z Selinger
Journal:  FEBS Lett       Date:  1998-08-21       Impact factor: 4.124

3.  Diinosine pentaphosphate: an antagonist which discriminates between recombinant P2X(3) and P2X(2/3) receptors and between two P2X receptors in rat sensory neurones.

Authors:  P M Dunn; M Liu; Y Zhong; B F King; G Burnstock
Journal:  Br J Pharmacol       Date:  2000-07       Impact factor: 8.739

4.  A binding site model and structure-activity relationships for the rat A3 adenosine receptor.

Authors:  P J van Galen; A H van Bergen; C Gallo-Rodriguez; N Melman; M E Olah; A P IJzerman; G L Stiles; K A Jacobson
Journal:  Mol Pharmacol       Date:  1994-06       Impact factor: 4.436

Review 5.  Molecular targets of guanine nucleotides in differentiation, proliferation and apoptosis.

Authors:  J A Yalowitz; H N Jayaram
Journal:  Anticancer Res       Date:  2000 Jul-Aug       Impact factor: 2.480

6.  Inosine binds to A3 adenosine receptors and stimulates mast cell degranulation.

Authors:  X Jin; R K Shepherd; B R Duling; J Linden
Journal:  J Clin Invest       Date:  1997-12-01       Impact factor: 14.808

Review 7.  Trophic effects of purines in neurons and glial cells.

Authors:  M P Rathbone; P J Middlemiss; J W Gysbers; C Andrew; M A Herman; J K Reed; R Ciccarelli; P Di Iorio; F Caciagli
Journal:  Prog Neurobiol       Date:  1999-12       Impact factor: 11.685

8.  A novel pharmacological approach to treating cardiac ischemia. Binary conjugates of A1 and A3 adenosine receptor agonists.

Authors:  K A Jacobson; R Xie; L Young; L Chang; B T Liang
Journal:  J Biol Chem       Date:  2000-09-29       Impact factor: 5.157

9.  Selective ligands for rat A3 adenosine receptors: structure-activity relationships of 1,3-dialkylxanthine 7-riboside derivatives.

Authors:  H O Kim; X D Ji; N Melman; M E Olah; G L Stiles; K A Jacobson
Journal:  J Med Chem       Date:  1994-11-11       Impact factor: 7.446

10.  Synthesis, biological activity, and molecular modeling of ribose-modified deoxyadenosine bisphosphate analogues as P2Y(1) receptor ligands.

Authors:  E Nandanan; S Y Jang; S Moro; H O Kim; M A Siddiqui; P Russ; V E Marquez; R Busson; P Herdewijn; T K Harden; J L Boyer; K A Jacobson
Journal:  J Med Chem       Date:  2000-03-09       Impact factor: 8.039
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  5 in total

1.  Methanocarba ring as a ribose modification in ligands of G protein-coupled purine and pyrimidine receptors: synthetic approaches.

Authors:  Dilip K Tosh; Kenneth A Jacobson
Journal:  Medchemcomm       Date:  2013-12-17       Impact factor: 3.597

2.  Synthesis and Effect of Conformationally Locked Carbocyclic Guanine Nucleotides on Dynamin.

Authors:  Kiran S Toti; John R Jimah; Veronica Salmaso; Jenny E Hinshaw; Kenneth A Jacobson
Journal:  Biomolecules       Date:  2022-04-16

3.  Design and in Vivo Characterization of A1 Adenosine Receptor Agonists in the Native Ribose and Conformationally Constrained (N)-Methanocarba Series.

Authors:  Dilip K Tosh; Harsha Rao; Amelia Bitant; Veronica Salmaso; Philip Mannes; David I Lieberman; Kelli L Vaughan; Julie A Mattison; Amy C Rothwell; John A Auchampach; Antonella Ciancetta; Naili Liu; Zhenzhong Cui; Zhan-Guo Gao; Marc L Reitman; Oksana Gavrilova; Kenneth A Jacobson
Journal:  J Med Chem       Date:  2019-01-03       Impact factor: 7.446

4.  Concise total synthesis of (±)-actinophyllic acid.

Authors:  Brett A Granger; Ivan T Jewett; Jeffrey D Butler; Stephen F Martin
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

5.  Purine (N)-Methanocarba Nucleoside Derivatives Lacking an Exocyclic Amine as Selective A3 Adenosine Receptor Agonists.

Authors:  Dilip K Tosh; Antonella Ciancetta; Eugene Warnick; Robert O'Connor; Zhoumou Chen; Elizabeth Gizewski; Steven Crane; Zhan-Guo Gao; John A Auchampach; Daniela Salvemini; Kenneth A Jacobson
Journal:  J Med Chem       Date:  2016-02-18       Impact factor: 7.446
  5 in total

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