Multinuclear magnetic resonance, electrospray ionization time-of-flight mass spectral and molecular modelling characterization of lithocholic acid amide esters with various nitrogen heterocycles

Magnetic Resonance in Chemistry

Volumn 41, Issue 8, 2003, Pages 567-576

  Virtanen, Elina ^a   Tamminen, Jari ^a   Haapala, Mervi ^a   Mänttäri, Pia ^a   Kauppinen, Reijo ^a   Kolehmainen, Erkki ^a  

^a UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

2,2 bipyridine 4,4 dicarboxylic acid; 113Cd NMR; 13C NMR; 15N NMR; 1H NMR; Electrospray ionization time of flight mass spectrometry; Lithocholic acid piperazine diamide; NMR

Indexed keywords

ELECTROSPRAY IONIZATION; ESTERS; MASS SPECTROMETRY; MOLECULAR MODELING;

113CD NMR; 13C NMR; 15N NMR; 1H NMR; 2,2′-BIPYRIDINE-4,4′ -DICARBOXYLIC ACID; BIPYRIDINES; CD-NMR; DICARBOXYLIC ACID; ELECTROSPRAY IONIZATION TIME-OF-FLIGHT MASS SPECTROMETRY; IONIZATION TIME OF FLIGHT MASS SPECTROMETRIES; LITHOCHOLIC ACID PIPERAZINE DIAMIDE; LITHOCHOLIC ACIDS;

NUCLEAR MAGNETIC RESONANCE;

AMIDE; DIPICOLINIC ACID; ESTER DERIVATIVE; LITHOCHOLIC ACID; NITROGEN; PIPERAZINE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; MASS SPECTROMETRY; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE DEPENDENCE;

EID: 0142087961     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/mrc.1218     Document Type: Article

References (51)

1. Bell DA, Anslyn EV. In Deoxycholic Acid and Related Hosts, Atwood JL, Davies JED, MacNicol DD, Vögtle F (eds). Comprehensive Supramolecular Chemistry, vol. 2, Elsevier: Oxford, 1996; 439.
2. Davis AP. Chem. Soc. Rev. 1993; 22: 243.
3. Maitra U. Curr. Sci. 1996; 71: 617.
4. Davis AP, Bonar-Law RP, Sanders JKM. In Receptors Based on Cholic Acid, Atwood JL, Davies JED, MacNicol DD, Vögtle F (eds). Comprehensive Supramolecular Chemistry, vol. 4. Elsevier: Oxford, 1996; 257.
5. Miyata M, Sada K. In Deoxycholic Acid and Related Hosts, Atwood JL, Davies JED, MacNicol DD, Vögtle F (eds). Comprehensive Supramolecular Chemistry, vol. 6. Elsevier: Oxford, 1996; 147.
6. Li Y, Dias JR. Chem. Rev. 1997; 97: 283.
7. Wallimann P, Marti T, Fürer A, Diederich F. Chem. Rev. 1997; 97: 1567.
8. Davis AP, Wareham RS. Angew. Chem., Int. Ed. Engl. 1999; 38: 2978.
9. Tamminen J, Kolehmainen E. Molecules 2000; 6: 21.
10. Hofmann AF. Ital. J. Gastroenterol. 1995; 27: 106.
11. Berlati F, Ceschel G, Clerici C, Pellicciari R, Roda A, Ronchi C. WO 9 400 126, 1994.
12. Marples BA, Stretton RJ. WO 9 013 298, 1990.
13. Enhsen A, Kramer W, Wess G. Drug Discov. Today 1998; 3: 409.
14. Ruff MR, Hill JM, Kwart LD, Pert CB. US Patent 5 446 026, 1995.
15. Li C, Peters AS, Meredith EL, Allman GW, Savage PB. J. Am. Chem. Soc. 1998; 120: 2961.
16. Li C, Budge LP, Driscoll CD, Willardson BM, Allman GW, Savage PS. J. Am. Chem. Soc. 1999; 121: 931.
17. Campazzi E, Cattabriga M, Marvelli L, Marchi A, Rossi R, Pieragnoli MR, Fogagnolo M. Inorg. Chim. Acta 1999; 286: 46.
18. Zuluaga F, Valderruten NE, Wagener KB. Polym. Bull. 1999; 42: 41.
19. Blagbrough IS, Al-Hadithi D, Geall AJ. Tetrahedron 2000; 56: 3439.
20. Muller JG, Ng MMP, Burrows J. J. Mol. Recognit. 1996; 9: 143.
21. Muellner S, Seipke G, Geisen K, Petri W. German Patent DE 4 234 537, 1994.
22. Kolehmainen E, Tamminen J, Lappalainen K, Torkkel T, Seppälä R. Synthesis 1996; 1082.
23. Tamminen J, Kolehmainen E, Haapala M, Linnanto J. Synthesis 2000; 1464.
24. Haapala M, Kolehmainen E, Tamminen J, Kauppinen R, Linnanto J, Virtanen E, Suontamo R, Vainiotalo P. Mater. Sci. Eng. C. 2001; 18: 21.
25. Virtanen E, Koivukorpi J, Tamminen T, Mänttäri P, Kolehmainen E. J. Organomet. Chem. 2003; 668: 43.
26. Tamminen J, Lappalainen K, Laihia K, Mänttäri P, Salo H, Kolehmainen E. Magn. Reson. Chem. 1999; 37: 163.
27. Kolehmainen E, Tamminen J, Kauppinen R, Linnanto J. J. Inclusion Phenom. Macrocycl. Chem. 1999; 35: 75.
28. Tamminen J, Kolehmainen E, Linnanto J, Salo H, Mänttäri P. Magn. Reson. Chem. 2000; 38: 877.
29. Dukh M, Drasar P, Cerny I, Pouzar V, Shriver JA, Král V, Sessler JL. Supramol. Chem. 2002; 14: 237.
30. Schneider H-J. Angew. Chem., Int. Ed. Engl. 1991; 30: 1417.
31. Zhang Y, Williams W, Torrence-Campbell C, Bowen WD, Rice KC. J. Med. Chem. 1998; 41: 4950.
32. Vögtle F. Supramolecular Chemistry, Wiley, Chichester, 1991; p. 16.
33. Hamilton AD, Goodman MS. US Patent 5 998 594, 1999.
34. Inanaga J, Hirata K, Saeki H, Katsuki T, Yamaguchi Y. Bull. Chem. Soc. Jpn. 1979; 52: 1989.
35. Tamminen J, Kolehmainen E, Haapala M, Salo H, Linnanto J. ARKIVOC 2000; 1: 90.
36. Dias JR, Gao H, Kolehmainen E. Spectrochim. Acta, Part A 2000; 56: 53.
37. Kohmoto S, Sakayori K, Kishikawa K, Yamamoto M. J. Chem. Soc., Perkin Trans. 2: 1999; 833.
38. Reschel M, Buděšínský M, Ĉerny I, Pouzar V, Drašar P. Collect. Czech. Chem. Commun. 2002; 67: 1709.
39. Bax A, Griffey RH, Hawkins BL. J. Magn. Reson. 1983; 55: 301.
40. Bax A, Subramanian S. J. Magn. Reson. 1986; 67: 565.
41. Bax A, Summers MF. J. Am. Chem. Soc. 1986; 108: 2093.
42. Hurd RE, John BK. J. Magn. Reson. 1991; 91: 648.
43. Rance M, Sørensen OW, Bodenhausen G, Wagner G, Ernst RR, Wüthrich K. Biochem. Biophys. Res. Commun. 1984; 117: 479.
44. Derome A, Williamson M. J. Magn. Reson. 1990; 88: 117.
45. Jeener J, Meier BH, Bachmann P, Ernst RR. J. Chem. Phys. 1979; 69: 4546.
46. Wagner G, Wüthrich K. J. Mol. Biol. 1982; 155: 347.
47. HyperChem, Version 4.5 for Windows. Hypercube: Waterloo, ON, 1994.
48. HyperChem, Version 6.03 for Windows. Hypercube: Waterloo, ON, 2000.
49. Allinger NL. J. Am. Chem. Soc. 1977; 99: 8127.
50. Allinger NL, Yuh YH. Quantum Chemistry Program Exchange, Bloomington, IN, Program No. 395; Burkert U, Allinger NL (eds). Molecular Mechanics. ACS Monograph 177. American Chemical Society: Washington, DC, 1982.
51. Stewart JJP. J. Comput. Chem. 1989; 10: 209.