Novel antagonists acting at the P2Y1 purinergic receptor: Synthesis and conformational analysis using potentiometric and nuclear magnetic resonance titration techniques

Journal of Medicinal Chemistry

Volumn 45, Issue 4, 2002, Pages 962-972

  Raboisson, Pierre ^a   Baurand, Anthony ^b   Cazenave, Jean Pierre ^b   Gachet, Christian ^b   Retat, Myriam ^a   Spiess, Bernard ^a   Bourguignon, Jean Jacques ^a  

^a Laboratoire de Pharmacochimie   (France)

^b INSERM   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2,N6 DIMETHYL 2' DEOXYADENOSINE 3',5' BISPHOSPHATE DERIVATIVE; ADENINE; ADENOSINE DERIVATIVE; ADENOSINE DIPHOSPHATE; ANTICOAGULANT AGENT; CALCIUM; G PROTEIN COUPLED RECEPTOR; HYDROGEN; METHYL GROUP; NITROGEN; PHOSPHATE; PHOSPHORUS 33; PURINE P2Y RECEPTOR; PURINE P2Y1 RECEPTOR; PURINERGIC RECEPTOR BLOCKING AGENT; RADIOLIGAND; UNCLASSIFIED DRUG;

ALKALINITY; ARTICLE; CALCIUM CELL LEVEL; CHEMICAL BOND; CONTROLLED STUDY; DIELECTRIC CONSTANT; DRUG CONFORMATION; DRUG POTENCY; DRUG SYNTHESIS; ELECTRON; HUMAN; HUMAN CELL; NUCLEAR MAGNETIC RESONANCE; PH; POTENTIOMETRY; PROTON TRANSPORT; STEREOCHEMISTRY; THROMBOCYTE AGGREGATION; THROMBOCYTE AGGREGATION INHIBITION; THROMBOCYTE SHAPE; TITRIMETRY;

EID: 0037075075     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0104062     Document Type: Article

References (59)

1. Receptors for purines and pyrimidines
2. Identification of the platelet ADP receptor targeted by antithrombotic drugs
3. ADP receptors of platelets and their inhibition
4. 1 receptor is necessary for adenosine 5′-diphosphate-induced platelet aggregation
5. 1 receptor-null mice
6. 1-deficient mice
7. 1 antagonist
8. 1 receptor antagonist
9. 6-methyl-2′-deoxyadenosine-3′,5′-bisphosphate
10. Identification of a P2Y-purinergic receptor that inhibits adenylyl cyclase but does not activate phospholipase C
11. Activity of novel adenine nucleotide derivatives as agonists and antagonists at recombinant rat P2X receptors
12. 1 receptors
13. Identification of potent, selective P2Y-purinoceptor agonists-structure- activity-relationships for 2-thioether derivatives of adenosine 5′-triphosphate
14. 1 receptor antagonists
15. 1 receptor ligands
16. Fluorescent adenosine and cytidine derrivatives
17. 6-etheno-2-aza-adenosine (2-aza-ε-adenosine): A new cytotoxic fluorescent nucleoside
18. 6-ethenoadenosine: Facile conversion of adenosine into 2-deuterated adenosine
19. Transamination of N,N-dimethylformamideazine
20. Efficient conversion of 6-aminopurines and nucleosides into 6-substituted analogues via novel 6-(1,2,4-triazol-4-yl)purine derivatives
21. Total synthesis of D- and L-myo-inositol 1,4,5-trisphosphate
22. A novel reagent for the synthesis of myo-inositol phosphates: N,N-diisopropyl dibenzyl phosphoramidine
23. Transient protection: Efficient one-flask syntheses of protected deoxynucleosides
24. Oligonucleoside synthesis. II. The use of substituted trityl groups
25. Pharmacology of AR-C69931MX and related compounds: From pharmacological tools to clinical trials
26. The determination of proton-binding sites by "nmr titrations"
27. Inframolecular protonation process of myo-inositol 1,4,5-tris(phosphate) and related compounds: Dynamics of the intramolecular interactions and evidence of C-H···O hydrogen bending
28. Inframolecular studies of the protonation of adenophostin A: Comparison with 1-D-myo-inositol 1,4,5-trisphosphate
29. Investigation of the inframolecular acid-base properties of D-myo-inositol 1,3,4,5-tetrakisphosphate and DL-myo-inositol 1,2,4,5-tetrakisphosphate
30. Synthesis, calcium mobilizing, and physico-chemical properties of D-chiro-inositol 1,3,4,6-tetrakisphosphate, a novel and potent ligand at the D-myo-inositol 1,4,5-trisphosphate receptor
31. Microscopic acid-base properties of D-myo-inositol 1,2,6-tris(phosphate) and its 3,4,5-trideoxy analogue-influence of the hydroxy groups of the myo-inositol ring
32. Inframolecular acid-base properties of myo-inositol 1,2,6-trisphosphate analogues-influence of the hydroxyl groups, phosphate configuration and intracyclic atom substitution
33. 31P NMR and potentiometry
34. Determination of microscopic acid dissociation constants by nuclear magnetic resonance spectrometry
35. A conformationally restricted cyclic phosphate analogue of inositol trisphosphate-synthesis and physicochemical properties
36. Nuclear magnetic resonance studies of the acid-base chemistry of amino acids and peptides. III. Determination of the microscopic and macroscopic acid dissociation constants of α,ω-diaminocarboxylic acids
37. Inositol phosphates: Inframolecular physicochemical studies, correlation with binding properties
38. 31P NMR studies
39. Studies of inter- and intramolecular interaction in mononucleotides by proton magnetic resonance
40. Nucleoside sites for transition metal ion binding
41. Solution properties of antiviral adenine-nucleotide analogues-the acid-base properties of 9-[2-(phosphonomethoxy)ethyl] adenine (pmea) and of its n1, n3 and n7 deaza derivatives in aqueous solution
42. Self-association and protonation of adenosine 5′-monophosphate in comparison with its 2′- and 3′-analogues and tubericin 5′-monophosphate (7-deaza-AMP)
43. 3+, and fluoride
44. 2+ and pH on nmr spectra and radioligand binding of inositol 1,4,5-trisphosphate
45. Molecular recognition of modified adenine nucleotides by the P2Y(1)-receptor. 1. A synthetic, biochemical, and NMR approach
46. Quantitation of the anomeric effect in adenosine and guanosine by comparison of the thermodynamics of the pseudorotational equilibrium of the pentofuranose moiety in N- and C-nucleosides
47. How does the steric effect drive the sugar conformation in the 3′-C-branched nucleosides?
48. How do the aglycones drive the pseudorotational equilibrium of the pentofuranose moiety in C-nucleosides?
49. How does the 3′-phosphate drive the sugar conformation in DNA?
50. The relation between proton-proton NMR coupling constants and substituent electronegativities. I. An empirical generalization of the Karplus equation
51. 3-linked ribo- and deoxyribodinucleoside monophosphates
52. Conformational analysis of the sugar ring in nucleosides. Improved for the interpretation of proton magnetic resonance coupling constants
53. 2+ inducer, at the D-myoinositol 1,4,5-trisphosphate receptor
54. How does the 2′-hydroxy group drive the pseudorotational equilibrium in nucleoside by the tuning of the 3′-gauche effect?
55. Synthesis of oligodeoxynucleotides containing N6-[13C-methyl]adenine and N2-[13C-methyl]guanine
56. L'agrégation plaquettaire: Outil d'investigation clinique et d'étude pharmacologiques-methodologie
57. Nuclear magnetic resonance as a tool for determining protonation constants of natural polyprotic bases in solution