Novel macrocyclic bile acid derivatives; Selective and easy binding of two cholic acid moieties at the 3-and 3'-positions

Synthesis

Volumn , Issue 24, 2009, Pages 4175-4182

  Lukashev, Nikolay V ^a   Kazantsev, Alexey V ^a   Averin, Alexey D ^a   Donez, Pavel A ^a   Baranov, Mikhail S ^a   Sievänen, Elina ^b   Kolehmainenb, Erkki ^b  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

Bile acids; Cholaphanes; Cyclizations; Cyclophanes; Macrocycles

Indexed keywords

BILE ACID; CHOLAPHANES; CYCLIZATIONS; CYCLOPHANES; MACROCYCLES;

AMIDES; CYCLIZATION; ESTERS;

BODY FLUIDS;

3ALPHA,3'ALPHA (ISOPHTHALOYLOXY)BIS (5BETA CHOLANE 7ALPHA,12ALPHA, 24 TRIOL); 3ALPHA,3ALPHA' (2,6 PYRIDINEDICARBONYLOXY)BIS (12ALPHA HYDROXY 5BETA CHOLAN 24 OIC ACID); 3ALPHA,3ALPHA' (ISOPHTHALOYLOXY)BIS (7ALPHA,12ALPHA DIHYDROXY 5BETA CHOLAN 24 OIC ACID); 3ALPHA,3ALPHA' (TEREPHTHALOYLOXY)BIS (7ALPHA,12ALPHA DIHYDROXY 5BETA CHOLAN 24 OIC ACID); BILE ACID; BIS (24 TRIPHENYLMETHOXY) 3ALPHA,3'ALPHA (ISOPHTHALOYLOXY)BIS (5BETA CHOLANE 7ALPHA,12ALPHA DIOL); BIS(PENTAFLUOROPHENYL) 3ALPHA,3ALPHA' (2,6 PYRIDINEDICARBONYLOXY)BIS (12ALPHA HYDROXY 5BETA CHOLAN 24 OATE); BIS(PENTAFLUOROPHENYL) 3ALPHA,3ALPHA' (ISOPHTHALOYLOXY)BIS (7ALPHA,12ALPHA DIHYDROXY 5BETA CHOLAN 24 OATE); BIS(PENTAFLUOROPHENYL) 3ALPHA,3ALPHA' (TEREPHTHALOYLOXY)BIS (7ALPHA,12ALPHA DIHYDROXY 5BETA CHOLAN 24 OATE); CHOLIC ACID; CYCLIC 3ALPHA,3'ALPHA (ISOPHTHALOYLOXY)BIS (5BETA CHOLAN 24 YLOXY) 2,5 THIOPHENEDICARBOXYLATE; CYCLIC 3ALPHA,3'ALPHA (ISOPHTHALOYLOXY)BIS (5BETA CHOLAN 24 YLOXY)ISOPTHALATE; CYCLIC 3ALPHA,3'ALPHA (ISOPHTHALOYLOXY)BIS (5BETA CHOLAN 24 YLOXY)OXALATE; CYCLIC 3ALPHA,3'ALPHA (ISOPHTHALOYLOXY)BIS (5BETA CHOLAN 24 YLOXY)TEREPHTHALATE; CYCLIC N,N' (3 OXA 1,5 PENTANEDIYL) 3ALPHA,3ALPHA' (2,6 PYRIDINECARBONYLOXY)BIS (12ALPHA HYDROXY 5BETA CHOLAN 24 AMIDE); CYCLIC N,N' (3,6 DIOXA 1,8 OCTANEDIYL) 3ALPHA,3'ALPHA (TEREPHTHALOYLOXY)BIS (5BETA CHOLAN 24 AMIDE); CYCLIC N,N' (3,6 DIOXA 1,8 OCTANEDIYL) 3ALPHA,3ALPHA' (ISOPHTHALOYLOXY)BIS (7ALPHA,12ALPHA DIHYDROXY 5BETA CHOLAN 24 AMIDE); CYCLIC N,N' (3,6 DIOXA 1,8 OCTANEDIYL) 3ALPHA,3ALPHA' (TEREPHTHALOYLOXY)BIS (7ALPHA,12ALPHA DIHYDROXY 5BETA CHOLAN 24 AMIDE); CYCLIC N,N' (ETHANEDIYL) 3ALPHA,3'ALPHA (TEREPHTHALOYLOXY)BIS (5BETA CHOLAN 24 AMIDE); DEOXYCHOLIC ACID DERIVATIVE; DIBENZYL 3ALPHA,3ALPHA' (2,6 PYRIDINEDICARBONYLOXY)BIS (12ALPHA HYDROXY 5BETA CHOLAN 24 OATE); DIBENZYL 3ALPHA,3ALPHA' (ISOPHTHALOYLOXY)BIS (7ALPHA,12ALPHA DIHYDROXY 5BETA CHOLAN 24 OATE); DIBENZYL 3ALPHA,3ALPHA' (TEREPHTHALOYLOXY)BIS (7ALPHA,12ALPHA DIHYDROXY 5BETA CHOLAN 24 OATE); LITHOCHOLIC ACID; MACROCYCLIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; AMINATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYCLIZATION; HYDROPHOBICITY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; POLYMERIZATION; STRUCTURE ANALYSIS;

EID: 78650729090     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217057     Document Type: Article

References (38)

1. Bonar-Law, R. P.; Sanders, J. K. M. Tetrahedron Lett. 1992, 33, 2071.
2. Virtanen, E.; Koivukorpi, J.; Tamminen, J.; Mänttäri, P.; Kolehmainen, E. J. Organomet. Chem. 2003, 668, 43.
3. Khatri, V. K.; Upreti, S.; Pandey, P. S. Org. Lett. 2006, 8, 1755.
4. Maitra, U.; D'Souza, L. J.; Kumar, P. V. Supramol. Chem. 1998, 10, 97.
5. Ghosh, S.; Choudhury, A. R.; Row, T. N. G.; Maitra, U. Org. Lett. 2005, 7, 1441.
6. Bonar-Law, R. P.; Mackay, L. G.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1993, 456.
7. Davis, A. P. Chem. Soc. Rev. 1993, 22, 243.
8. Bhattarai, K. M.; Davis, A. P.; Perry, J. J.; Walter, C. J. J. Org. Chem. 1997, 62, 8463.
9. Rasmussen, B. S.; Elezcano, U.; Skrydstrup, T. J. Chem. Soc., Perkin Trans. 1 2002, 1723.
10. Chattopadhyay, P.; Pandey, P. S. Bioorg. Med. Chem. Lett. 2007, 17, 1553.
11. Chattopadhyay, P.; Pandey, P. S. Tetrahedron 2006, 62, 8620.
12. Kikuchi, J.-I.; Murakami, Y. J. Inclusion Phenom. Mol. Recognit. Chem. 1998, 32, 209.
13. Gao, H.; Dias, J. R. Synth. Commun. 1997, 27, 757.
14. Dias, J. R.; Pascal, R. A.; Morrill, J.; Holder, A. J.; Gao, H.; Barnes, C. J. Am. Chem. Soc. 2002, 124, 4647.
15. Gao, H.; Dias, J. R. Croat. Chem. Acta 1998, 71, 827.
16. Davis, A. P.; Walsh, J. J. Chem. Commun. 1996, 449.
17. Bonar-Law, R. P.; Davis, A. P. Tetrahedron 1993, 49, 9829.
18. Tian, Z.; Cui, H.; Wang, Y. Synth. Commun. 2002, 32, 3821
19. Albert, D.; Feigel, M.; Benet-Buchholz, J.; Boese, R. Angew. Chem. Int. Ed. 1998, 37, 2727.
20. Albert, D.; Fiegel, M. Tetrahedron Lett. 1994, 35, 565.
21. Rivera, D. G.; Wessjohann, L. Molecules 2007, 12, 1890.
22. Wessjohann, L. A.; Rivera, D. G.; Coll, F. J. Org. Chem. 2006, 71, 7521.
23. Tamminen, J.; Kolehmainen, E.; Haapala, M.; Linnanto, J. Synthesis 2000, 1464.
24. Pandey, P. S.; Rai, R.; Singh, R. B. J. Chem. Soc., Perkin Trans. 1 2002, 918.
25. Kolehmainen, E.; Tamminen, J.; Lappalainen, K.; Torkkel, T.; Seppälä, R. Synthesis 1996, 1082.
26. Pandey, P. S.; Rai, R.; Singh, R. B. Tetrahedron 2002, 58, 355.
27. Ra, C. S.; Cho, S. W.; Choi, J. W. Bull. Korean Chem. Soc. 2000, 21, 342.
28. Łotowski, Z.; Guzmanski D. Monatsh. Chem. 2005, 136, 153.
29. Nair, V.; Prabhakaran, J.; Eigendorf, G. K. Synth. Commun. 1997, 27, 3095.
30. Averin, A. D.; Ranyuk, E. R.; Lukashev, N. V.; Beletskaya, I. P. Chem. Eur. J. 2005, 11, 7030.
31. Averin, A. D.; Ranyuk, E. R.; Lukashev, N. V.; Golub, S. L.; Buryak, A. K.; Beletskaya, I. P. Tetrahedron Lett. 2008, 49, 1188.
32. Czajkowska, D.; Morzycki, J. W. Tetrahedron Lett. 2007, 48, 2851.
33. Latyshev, G. V.; Baranov, M. S.; Kazantsev, A. V.; Averin, A. D.; Lukashev, N. V.; Beletskaya, I. P. Synthesis 2009, 2605.
34. Valkonen, A.; Sievänen, E.; Ikonen, S.; Lukashev, N. V.; Donez, P. A.; Averin, A. D.; Lahtinen, M.; Kolehmainen, E. J. Mol. Struct. 2007, 846, 65.
35. Kohmoto, S.; Fukui, D.; Nagashima, T.; Kishikawa, K.; Yamamoto, M.; Yamada, K. Chem. Commun. 1996, 1869.
36. Li, Y.; Dias, J. R. Synthesis 1997, 425.
37. Vijayalakshmi, N.; Maitra, U. Macromolecules 2006, 39, 7931.
38. Li, H.; Wang, L. X. Org. Biomol. Chem. 2003, 1, 3507.