A new series of heteroaromatic receptors containing the 1,3-bis(6-oxopyridazin-1-yl)propane unit: Their selective transport ability towards NH4+ in relation to Na+, K+ and Ca2+

Tetrahedron

Volumn 60, Issue 4, 2004, Pages 979-986

  Campayo, Lucrecia ^a   Pardo, Mercedes ^a   Cotillas, Ana ^a   Jaúregui, Oscar ^a   Yunta, Maria J R ^a   Cano, Carmen ^a   Gomez Contreras, Fernando ^a   Navarro, Pilar ^b   Sanz, Ana M ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

Ammonium carriers; Heteroaromatic receptors; Pyridazine macrocycles

Indexed keywords

1,3 BIS(3 BUTOXY 6 OXOPYRIDAZIN 1 YL)PROPANE; 1,3 BIS(6 OXOPYRIDAZIN 1 YL)PROPANE; 1,3 BIS[3 (2 HYDROXYETHOXY) 6 OXOPYRIDAZIN 1 YL]PROPANE; 1,3 BIS[3 (3 HYDROXYPROPOXY) 6 OXOPYRIDAZIN 1 YL]PROPANE; 1,3 BIS[3 [2 (2 HYDROXYETHOXY)ETHOXY] 6 OXOPYRIDAZIN 1 YL]PROPANE; 1,3 BIS[3 [2 [2 (2 HYDROXYETHOXY)ETHOXY]ETHOXY] 6 OXOPYRIDAZIN 1 YL]PROPANE; 10,13,16,19,27,30,33,36 OCTAOXA 1,5,41,42,43 PENTAAZATETRACYCLO[35.3.1.1 5,9 .1 21,25 ]TRITETRACONTA 7,9(42),18,20,22(37),31(35),32 HEPTAEN 6,34 DIONE; 10,13,16,24,27,30 HEXAOXA 1,5,35,36,37 PENTAAZATETRACYCLO[29.3.1.1 5,9 .1 18,22 ]HEPTATRIACONTA 7,9(36),18,20,22(37),31(35),32 HEPTAEN 6,34 DIONE; 10,13,21,24 TETRAOXA 1,5,29,30,31 PENTAAZATETRACYCLO[23.3.1.1 5,9 .1 15,19 ]UNTRIACONTA 7,9(30),15,17,19(31),25(29),26 HEPTAEN 6,28 DIONE; 10,14,22,26 TETRAOXA 1,5,31,32,33 PENTAAZATETRACYCLO[25.3.1.1 5,9 .1 16,20 ]TRITRIACONTA 7,9(32),16,18,20(33),27(31),28 HEPTAEN 6,30 DIONE; AMMONIUM DERIVATIVE; CALCIUM ION; IONOPHORE; POTASSIUM ION; PYRIDAZINE DERIVATIVE; RECEPTOR SUBUNIT; RECOMBINANT RECEPTOR; SODIUM ION; UNCLASSIFIED DRUG;

ARTICLE; CALCIUM TRANSPORT; CHEMICAL REACTION; DRUG RECEPTOR BINDING; HYDROGEN BOND; ION TRANSPORT; MOLECULAR INTERACTION; MOLECULAR MODEL; POTASSIUM TRANSPORT; PRIORITY JOURNAL; SODIUM TRANSPORT; SYNTHESIS;

EID: 0346339664     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.11.040     Document Type: Article

References (38)

1. Rüdiger V., Schneider H.J., Solov'ev V.P., Kazachenko V.P., Raevsky O.A. Eur. J. Org. Chem. 1999;1847-1856.
2. Bülhman P., Prestch E., Bakker E. Chem. Rev. 98:1998;1593-1687.
3. Strömberg N., Hulth S. Anal. Chim. Acta. 443:2002;215-225.
4. Dobler M. Atwood J.L., Davies J.E.D., Mac Nicol D.D., Vögtle F. Comprehensive supramolecular chemistry. Vol. 1:1996;276-313 Pergamon, Oxford.
5. Lehn J.M. Angew. Chem., Int. Ed. Engl. 27:1988;89-112.
6. Zhang X.X., Bradshaw J.S., Izatt R.M. Chem. Rev. 97:1997;3313-3361.
7. Rodriguez-Franco M.I., Navarro P. J. Chem. Soc. Chem. Commun. 1988;1365-1367.
8. Navarro P., Rodríguez-Franco M.I. Trends Org. Chem. 4:1993;69-100.
9. Navarro P., Pueyo E., Rodriguez-Franco M.I., Samat A. Tetrahedron. 46:1990;2917-2926.
10. Campayo L., Bueno J.M., Ochoa C., Navarro P., Samat A. Tetrahedron Lett. 34:1993;7299-7300.
11. Campayo L., Bueno J.M., Navarro P., Ochoa C., Jimenez-Barbero J.M., Pepe G., Samat A. J. Org. Chem. 62:1997;2684-2693.
12. Reviriego F., Navarro P., Domenech A., Garcia-España E. J. Chem. Soc., Perkin Trans. 2. 2002;1634-1638.
13. Sanz A.M., Navarro P., Gomez-Contreras F., Pardo M., Pepe G., Samat A. Can. J. Chem. 76:1998;1174-1179.
14. Reviriego F., Navarro P., Domenech A., Garcia-España E. J. Supramol. Chem. 2:2002;115-122.
15. Fierros M., Rodriguez-Franco M.I., Navarro P., Conde S. Bioorg. Med. Chem. Lett. 21:1994;2523-2526.
16. Rodriguez-Franco M.I., Fierros M., Martinez A., Navarro P., Conde S. Bioorg. Med. Chem. 5:1997;363-367.
17. Druey J., Meier K., Eichenberger K. Helv. Chim. Acta. 37:1954;121-133.
18. Live D., Chan S.I. J. Am. Chem. Soc. 98:1976;3769-3778.
19. Buchanan G.W. Prog. NMR Spectrosc. 34:1999;327-377.
20. Lauterbach M. J. Phys. Chem. B. 102:1998;245-256.
21. Troxler A.L., Wipff G. Anal. Sci. 14:1998;43-56.
22. Durand S., Dognon J.P., Guilbaud P., Rabbe C., Wipff G. J. Chem. Soc., Perkin Trans. 2. 2000;705-714.
23. Hobza P., Kabelaç Sponer J., Mejzlik P., Vondrasek J. J. Comput. Chem. 18:1997;1136-1150.
24. Fyles T.M. Osa T., Atwood J.L. Bioorganic chemistry frontiers. Topics in inclusion science. Vol. 2:1991;59-110 Kluwer Academic. Chapter 2.
25. Morf W.E., Ammann D., Bissig R., Pretsch E., Simon W. Izatt R.M., Christensen J.J. Progress in macrocyclic chemistry. Vol. 1:1979;2-16 Wiley, New York. Chapter 1.
26. Cornell W.D., Cieplak P., Bayly C.I., Gould I.R., Merz K.M., Ferguson D.M., Spellmeyer D.C., Fox T., Caldwell J.W., Kollman P.A. J. Am. Chem. Soc. 117:1995;5179-5197.
27. Hyperchem 6.0 (Hypercube Inc.).
28. Fox T., Scanlan T.S., Kollman P.A. J. Am. Chem. Soc. 119:1997;11571- 11577.
29. Grootenhuis P.D., Kollman P.A. J. Am. Chem. Soc. 111:1989;2152-2158.
30. Moyna G., Hernandez G., Williams H.J., Nachman R.J., Scott A.I. J. Chem. Inf. Comput. Sci. 37:1997;951-956.
31. Boden C.D.J., Patenden G. J. Comput. -Aided Mol. Des. 13:1999;153-166.
32. http://www.amber.ucsf.edu/amber .
33. Hopfinger A.J., Pearlstein R.A. J. Comput. Chem. 5:1984;486-499.
34. Glennon T.M., Zheng Y.-J., Le Grand S.M., Scutzberg B.A., Merz K.M. J. Comput. Chem. 15:1994;1019-1040.
35. Urban J.J., Cronin C.W., Roberts R.R., Famini G.R. J. Am. Chem. Soc. 119:1997;12292-12299.
36. Wang J., Kollman P.A. J. Am. Chem. Soc. 120:1998;11106-11114.
37. Weiner S.J., Kollman P.A., Case D.A., Singh U.C., Ghio C., Alagona G., Profeta S., Weiner P. J. Am. Chem. Soc. 106:1984;765-784.
38. Hill S.E., Feller D. Int. J. Mass Spectrom. 201:2000;41-58.