Convergent synthesis of the potent P2Y receptor antagonist MG 50-3-1 based on a regioselective Ullmann coupling reaction

Molecules

Volumn 17, Issue 3, 2012, Pages 2599-2615

  Baqi, Younis ^a   Müller, Christa E ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Anthraquinone; Convergent synthesis; P2Y receptor antagonist; Regioselective coupling; Ullmann reaction

Indexed keywords

ANILINE; ANILINE DERIVATIVE; ANTHRACENE DERIVATIVE; ANTHRAQUINONE DERIVATIVE; BROMAMINE ACID; COPPER; ETHYLAMINE; MG 50 3 1; MG 50-3-1; PURINERGIC P2Y RECEPTOR ANTAGONIST; SOLVENT; SULFONIC ACID DERIVATIVE; TRIAZINE DERIVATIVE; TRIETHYLAMINE;

ARTICLE; CATALYSIS; CHEMISTRY; HUMAN; MICROWAVE RADIATION; PH; SYNTHESIS;

ANILINE COMPOUNDS; ANTHRACENES; ANTHRAQUINONES; CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; COPPER; ETHYLAMINES; HUMANS; HYDROGEN-ION CONCENTRATION; MICROWAVES; PURINERGIC P2Y RECEPTOR ANTAGONISTS; SOLVENTS; SULFONIC ACIDS; TRIAZINES;

EID: 84858984631     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17032599     Document Type: Article

References (33)

1. Burnstock, G. Physiology and pathophysiology of purinergic neurotransmission. Physiol. Rev. 2007, 87, 659-797. (Pubitemid 47084682)
2. Burnstock, G. Pathophysiology and therapeutic potential of purinergic signaling. Pharmacol. Rev. 2006, 58, 58-86.
3. Müller, C. E. P2-pyrimidinergic receptors and their ligands. Curr. Pharm. Des. 2002, 8, 2353-2369. (Pubitemid 35331541)
4. Brunschweiger, A.; Müller, C. E. P2 receptors activated by uracil nucleotides-An update. Curr. Med. Chem. 2006, 13, 289-312.
5. Hancock, A. A. The challenge of drug discovery of a GPCR target: Analysis of preclinical pharmacology of histamine H3 antagonists/inverse agonists. Biochem. Pharmacol. 2006, 71, 1103-1113. (Pubitemid 43361919)
6. Burnstock, G. Purinergic signaling and vascular cell proliferation and death. Arterioscler. Thromb. Vasc. Biol. 2002, 22, 364-373. (Pubitemid 34218740)
7. Gachet, C. P2 receptors, platelet function and pharmacological implications. Thromb. Haemost. 2008, 99, 466-472. (Pubitemid 351549282)
8. Gachet, C. The platelet P2 receptors as molecular targets for old and new antiplatelet drugs. Pharmacol. Ther. 2005, 108, 180-192. (Pubitemid 41528788)
9. Gachet, C. Regulation of platelet functions by P2 receptors. Annu. Rev. Pharmacol. Toxicol. 2006, 46, 277-300. (Pubitemid 43271191)
10. 12 receptor antagonists: A rapidly expanding group of antiplatelet agents. Eur. Heart J. 2006, 27, 1010-1012.
11. Cattaneo, M. Aspirin and clopidogrel efficacy, safety, and the issue of drug resistance Arterioscler. Thromb. Vasc. Biol. 2004, 24, 1980-1988.
12. Nawarskas, J. J.; Clark, S. M. Ticagrelor: A novel reversible oral antiplatelet agent. Cardiol. Rev. 2011, 19, 95-100.
13. 1 receptor-null mice. J. Clin. Invest. 1999, 104, 1731-1737. (Pubitemid 30053190)
14. 1-deficient mice. Nat. Med. 1999, 5, 1199-1202. (Pubitemid 29474427)
15. 11 purinoceptors in parasympathetic inhibition of colonic smooth muscle. Pharmacol. Exp. Ther. 2008, 324, 1055-1063. (Pubitemid 351397835)
16. Bean, B. P. Pharmacology and electrophysiology of ATP-activated ion channels. Trends Pharmacol. Sci. 1992, 13, 87-90.
17. Inoue, K.; Nakazawa, K.; Ohara-Imaizumi, M.; Obama, T.; Fujimori, K.; Takanaka, A. Antagonism by reactive blue 2 but not by brilliant blue G of extracellular ATP-evoked responses in PC12 phaeochromocytoma cells. Br. J. Pharmacol. 1991, 102, 851-854.
18. Nakazawa, K.; Inoue, K.; Fujimori, K.; Takanaka, A. Effects of ATP antagonists on purinoceptoroperated inward currents in rat phaeochromocytoma cells. Pflügers Arch. 1991, 418, 214-219.
19. Brown, J.; Brown, C. A. Evaluation of reactive blue 2 derivatives as selective antagonists for P2Y receptors. Vasc. Pharmacol. 2003, 39, 309-315. (Pubitemid 36830734)
20. Tuluc, F.; Bültmann, R.; Glänzel, M.; Frahm, A. W.; Starke, K. P2-receptor antagonists: IV. Blockade of P2-receptor subtypes and ecto-nucleotidases by compounds related to reactive blue 2. Naunyn Schmiedeberg's Arch. Pharmacol. 1998, 357, 111-120. (Pubitemid 28085510)
21. Glänzel, M.; Bültmann, R.; Starke, K.; Frahm, A. W. Structure-activity relationships of novel P2-receptor antagonists structurally related to Reactive Blue 2. Eur. J. Med. Chem. 2005, 40, 1262-1276. (Pubitemid 41618267)
22. Baqi, Y.; Hausmann, R.; Rosefort, C.; Rettinger, J.; Schmalzing, G.; Müller, C. E. Discovery of potent competitive antagonists and positive modulators of the P2X2 receptor. J. Med. Chem. 2011, 54, 817-830.
23. 2 receptor antagonists. Bioorg. Med. Chem. Lett. 2008, 18, 223-227.
24. 12 receptors. J. Med. Chem. 2009, 52, 3784-3793.
25. 12-receptor. J. Pharmacol. Exp. Ther. 2009, 331, 648-655.
26. Baqi, Y.; Weyler, S.; Iqbal, J.; Zimmermann, H.; Müller, C. E. Structure-activity relationships of anthraquinone derivatives derived from bromaminic acid as inhibitors of ectonucleoside triphosphate diphosphohydrolases (E-NTPDases). Purinerg. Signal. 2009, 5, 91-106.
27. Baqi, Y.; Lee, S.-Y.; Iqbal, J.; Ripphausen, P.; Lehr, A.; Scheiff, A. B.; Zimmermann, H.; Bajorath, J.; Müller, C. E. Development of potent and selective inhibitors of ecto-5'-nucleotidase based on an anthraquinone scaffold. J. Med. Chem. 2010, 53, 2076-2086.
28. Baqi, Y.; Müller, C. E. Rapid and efficient microwave-assisted copper (0)-catalyzed Ullmann coupling reaction: general access to anilinoanthraquinone derivatives. Org. Lett. 2007, 9, 1271-1274.
29. Baqi, Y.; Müller, C. E. Synthesis of alkyl-and aryl-amino- substituted anthraquinone derivatives by microwave-assisted copper (0)-catalyzed Ullmann coupling reactions. Nat. Protoc. 2010, 5, 945-953.
30. Paine, A. J. Mechanisms and models for copper mediated nucleophilic aromatic substitution. 2. A single catalytic species from three different oxidation states of copper in an Ullmann synthesis of triarylamines. J. Am. Chem. Soc. 1987, 109, 1496-1502.
31. Lewin, A. H.; Cohen, T. The mechanism of the Ullmann reaction. Detection of an organocopper intermediate. Tetrahedron Lett. 1965, 50, 4531-4536.
32. Ritter, S. C. Cu (I)-Catalyzed "Click-Chemistry" Design of a Chemical Photomultiplier Target-Guided Synthesis of Bidentate Metal-Complex Receptors. Ph. D. thesis, University of Regensburg, Germany, 2007.
33. Ritter, S. C.; König, B. Signal amplification and transduction by photo-activated catalysis. Chem. Commun. 2006, 4694-4696. (Pubitemid 44772284)