Synthesis of new chiral xanthone derivatives acting as nerve conduction blockers in the rat sciatic nerve

European Journal of Medicinal Chemistry

Volumn 55, Issue , 2012, Pages 1-11

  Fernandes, Carla ^a   Oliveira, Laura ^a   Tiritan, Maria Elizabeth ^a,b   Leitao, Luís ^a   Pozzi, Angelo ^a   Noronha Matos, José Bernardo ^a   Correia De Sá, Paulo ^a   Pinto, Madalena M ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b INSTITUTO DE INVESTIGAÇÃO E FORMAÇÃO AVANÇADA EM CIÊNCIAS E TECNOLOGIAS DA SAÚDE   (Portugal)

Author keywords

Action potential blockade; Chiral xanthone derivatives; Hypotonic haemolysis; Local anaesthetic like properties; Sciatic nerve; TBTU

Indexed keywords

6 METHOXY 9 OXO 9H XANTHENE 2 CARBOXYLIC ACID; 6 METHOXY 9 OXO N (1 (4 TOLYL)ETHYL)9H XANTHENE 2 CARBOXAMIDE; AMINOALCOHOL; BENZOTRIAZOL 1 YL TETRAMETHYLLURONIUM TETRAFLUOROBORATE; BORIC ACID; N (1 HYDROXY 3 METHYLBUTAN 2 YL) 6 METHOXY 9 OXO 9H XANTHENE 2 CARBOXAMIDE; N (1 HYDROXY 4 METHYLPENTAN 2 YL) 6 METHOXY 9 OXO 9H XANTHENE 2 CARBOXAMIDE; UNCLASSIFIED DRUG; VOLTAGE GATED CHANNEL FORMING PROTEIN; XANTHONE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL MEMBRANE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DRUG SYNTHESIS; ENANTIOMER; HEMOLYSIS; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; INFRARED SPECTROMETRY; ION CURRENT; LOCAL ANESTHESIA; MASS SPECTROMETRY; NERVE BLOCK; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; SCIATIC NERVE;

ANIMALS; CHEMISTRY TECHNIQUES, SYNTHETIC; MALE; NERVE BLOCK; NEURAL CONDUCTION; RATS; RATS, WISTAR; SCIATIC NERVE; STEREOISOMERISM; XANTHONES;

EID: 84865764202     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.06.049     Document Type: Article

References (43)

1. H. Caner, E. Groner, and L. Levy Trends in the development of chiral drugs DDT 9 3 2004 105 110
2. I. Agranat, and S.R. Wainschtein The strategy of enantiomer patents of drugs DDT 15 5-6 2010 163 170
3. http://www.imshealth.com (2011-03-11).
4. D.R. Brocks Drug disposition in three dimensions: an update on stereoselectivity in pharmacokinetics Biopharm. Drug Dispos. 27 2006 387 406
5. B. Kasprzyk-Hordern Pharmacologically active compounds in the environment and their chirality Chem. Soc. Rev. 39 2010 4466 4503
6. Food and Drug Administration, Federal Register 57, FR 22249 (1992).
7. Directive 75/318/EEC (1993).
8. M.M.M. Pinto, M.E. Sousa, and M.S.J. Nascimento Xanthone derivatives: new insights in biological activities Curr. Med. Chem. 12 21 2005 2517 2538
9. M.M.M. Pinto, and E.P. Sousa Natural and synthetic Xanthonolignoids: chemistry and biological activities Curr. Med. Chem. 10 2003 1 12
10. R.A.P. Castanheiro, M.M.M. Pinto, A.M.S. Silva, S.M.M. Cravo, L. Gales, A.M. Damas, N. Nazareth, M.S.J. Nascimento, and G. Eaton Dihydroxyxanthones prenylated derivatives: synthesis, structure elucidation, and growth inhibitory activity on human tumor cell lines with improvement of selectivity for MCF-7 Bioorg. Med. Chem. 15 2007 6080 6088
11. E. Sousa, A. Paiva, N. Nazareth, L. Gales, A.M. Damas, M.S.J. Nascimento, and M. Pinto Bromoalkoxyxanthones as promising antitumor agents: synthesis, crystal structure and effect on human tumor cell lines Eur. J. Med. Chem. 44 2009 3830 3835
12. A. Palmeira, M.H. Vasconcelos, A. Paiva, M.X. Fernandes, M. Pinto, and E. Sousa Dual inhibitors of P-glycoprotein and tumor cell growth: (re)discovering thioxanthones Biochem. Pharmacol. 83 2012 57 68
13. A. Palmeira, A. Paiva, E. Sousa, H. Seca, G.M. Almeida, R.T. Lima, M.X. Fernandes, M. Pinto, and M.H. Vasconcelos Insights into the in vitro antitumor mechanism of action of a new pyranoxanthone Chem. Biol. Drug Des. 76 2010 43 58
14. E.P. Sousa, A.M.S. Silva, M.M.M. Pinto, M.M. Pedro, F.A.M. Cerqueira, and M.S.J. Nascimento Isomeric Kielcorins and Dihydroxyxanthones: synthesis, structure elucidation, and inhibitory activities of growth of human cancer cell lines and on the proliferation of human lymphocytes in vitro Hel. Chim. Acta 85 2002 2862 2876
15. H. Marona Synthesis and anticonvulsant effects of some aminoalkanolic derivatives of xanthone Pharmazie 53 1998 672 676
16. H. Marona, N. Szkaradek, M. Kubacka, M. Bednarski, B. Filipek, M. Cegla, and E. Szneler Synthesis and evaluation of some xanthone derivatives for anti-arrhythmic, hypotensive properties and their affinity for adrenergic receptors Arch. Pharm. Chem. Life Sci. 341 2008 90 98
17. M. Jastrzêbska-Wiêsek, T. Librowski, T. Czarnecki, H. Marona, and G. Nowak Central activity of new xanthone derivatives with chiral center in some pharmacological tests in Mice Pol. J. Pharmacol. 55 3 2003 461 465
18. H. Marona, N. Szkaradek, A. Rapacz, B. Filipek, M. Dybała, A. Siwek, M. Cegła, and E. Szneler Preliminary evaluation of pharmacological properties of some xanthone derivatives Bioorg. Med. Chem. 17 2009 1345 1352
19. G.W. Rewcastle, G.J. Atwell, B.C. Baguley, M. Boyd, L.L. Thomsen, L. Zhuang, and W.A. Denny Potential antitumor agents. 63. Structure-activity relationships for side-chain analogues of the colon 38 active agent 9-Oxo-9H-xanthene-4-acetic acid J. Med. Chem. 34 1991 2864 2870
20. H. Marona Evaluation of some 2-substituted derivatives of xanthone for anticonvulsant properties Pharmazie 53 1998 405 409
21. H. Marona, E. Pekala, L. Antkiewicz-Michaluk, M. Walczak, and E. Szneler Anticonvulsant activity of some xanthone derivatives Bioorg. Med. Chem. 16 2008 7234 7244
22. M. Jastrzebska-Wiesek, R. Czarnecki, and H. Marona The anticonvulsant, local anesthetic and hemodynamic properties of some chiral aminobutanol derivatives of xanthone Acta Pol. Pharm.-Drug Res. 65 5 2008 591 601
23. H. Marona, N. Szkaradek, E. Karczewska, D. Trojanowska, A. Budak, P. Bober, W. Przepiórka, M. Cegla, and E. Szneler Antifungal and antibacterial activity of the newly synthesized 2-Xanthone derivatives Arch. Pharm. Chem. Life Sci. 342 2009 9 18
24. L. Wang, J. Kang, I. Chen, C. Teng, and C. Lin Antihypertensive and vasorelaxing activities of synthetic xanthone derivatives Bioorg. Med. Chem. 10 3 2002 567 572
25. J.R. Pfister, R.W. Ferraresi, I.T. Harrison, W.H. Rooks, A.P. Roszkowski, A. Van Horn, and J.H. Fried Xanthone-2-carboxilic acids, a new series of antiallergic substances J. Med. Chem. 15 1972 1032 1035
26. W.T. Jackson, R.J. Boyd, L.L. Froelich, D.M. Gapinski, B.E. Mallett, and J.S. Sawyer Design, synthesis, and pharmacological evaluation of potent xanthone dicarboxylic acid leukotriene B 4 receptor antagonists J. Med. Chem. 36 1993 1726 1734
27. F. Albericio, M.A. Bailén, R. Chinchilla, D.J. Dodsworth, and C. Nájera 2-Mercaptopyridine-1-oxide-based peptide coupling reagents Tetrahedron 57 2001 9607 9613
28. S. Balalaie, M. Mahdidoust, and R. Eshaghi-Najafabadi 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate as an efficient coupling reagent for the amidation and phenylhydrazation of carboxylic acids at room temperature J. Iran. Chem. Soc. 4 3 2007 364 369
29. S. Han, and Y. Kim Recent development of peptide coupling reagents in organic synthesis Tetrahedron 60 2004 2447 2467
30. C.A.G.N. Montalbetti, and V. Falque Amide bond formation and peptide coupling Tetrahedron 61 2005 10827 10852
31. T.I. Al-Warhi, H.M.A. Al-Hazimi, and A. El-Faham Recent development in peptide coupling reagents J. Saudi Chem. Soc. 16 2 2012 97 116
32. B. Hille Ionic Channels of Excitable Membranes second ed. 1992 MA: Sinauer Associates Sunderland pp. 390-460
33. D. Ma, and Q. Cai N, N-Dimethyl glycine-promoted Ullmann coupling reaction of phenol and aryl halides Org. Lett. 5 21 2003 3799 3802
34. E.J. Simons, E. Bellas, M.W. Lawlor, and D.S. Kohane Effect of chemical permeation enhancers on nerve blockade Mol. Pharmaceutics 6 2009 265 273
35. J.H. Crowe, L.M. Crowe, J.F. Carpenter, and C.A. Wistrom Stabilization of dry phospholipid bilayers and proteins by sugars Biochem. J. 242 1987 1 10
36. G. Strauss, and H. Hauser Stabilization of lipid bilayer vesicles by sucrose during freezing Proc. Nat. Acad. Sci. USA 83 1986 2422 2426
37. S.V.P. Malheiros, L.M.A. Pinto, L. Gottardo, D.K. Yokaichiya, L.F. Fraceto, N.C. Meirelles, and E. Paula A new look at the hemolytic effect of local anesthetics, considering their real membrane/water partioning at pH 7.4 Biophys. Chem. 110 2004 213 221
38. S.A. Matlin, M.E. Tiritan, A.J. Crawford, Q.B. Cass, and D.R. Boyd HPLC with carbohydrate carbamate chiral phases: influence of chiral phase structure on enantioselectivity Chirality 6 1994 135 140
39. S.A. Matlin, M.E. Tiritan, Q.B. Cass, and D.R. Boyd Enantiomeric resolution of chiral sulfoxides on polysaccharide phases by HPLC Chirality 8 1996 147 152
40. T. Mert, Y. Gunes, D. Ozcengis, I. Gunay, and S. Polat Comparative effects of lidocaine and tramadol on injured peripheral nerves Eur. J. Pharmacol. 543 2006 54 62
41. H. Bergmeyer Lactic Dehydrogenase, Methods of Enzymatic Analysis 1963 pp. 736-743
42. P. Seeman, and J.I. Weinstein Erythrocyte membrane stabilization by tranquilizers and antihistamines Biochem. Pharmac. 15 1966 1737 1752
43. M.A. Timóteo, and J.A. Ribeiro The effect of sodium tripolyphosphate on erythrocytes Actas Bioq. 2 1989 201 205