Hydrogen sulfate-induced organogelation of a bile acid based anion-receptor

Tetrahedron Letters

Volumn 52, Issue 28, 2011, Pages 3558-3560

  Tripathi, Anamica ^a   Pandey, Pramod S ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY DELHI   (India)

Author keywords

Anion recognition; Bile acid; Hydrogen sulfate; Organogel

Indexed keywords

BILE ACID; BISULFATE SODIUM; INORGANIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; GELATION; SYNTHESIS;

EID: 79958267346     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.04.056     Document Type: Article

References (74)

1. P. Terech, and R.G. Weiss Chem. Rev. 97 1997 3133
2. D.J. Abdallah, and R.G. Weiss Adv. Mater. 12 2000 1237
3. L.A. Estroff, and A.D. Hamilton Chem. Rev. 104 2004 1201
4. N.M. Sangeetha, and U. Maitra Chem. Soc. Rev. 34 2005 821
5. M. George, and R.G. Weiss Acc. Chem. Res. 39 2006 489
6. A. Ajayaghosh, and V.K. Praveen Acc. Chem. Res. 40 2007 644
7. P. Dastidar Chem. Soc. Rev. 37 2008 2699
8. J.W. Steed Chem. Soc. Rev. 39 2010 3686
9. G. Bonacucina, M. Cespi, M. Misici-Falzi, and G.F. Palmieri J. Pharm. Sci. 98 2009 1
10. A. Moutlsky, M. Lafleur, A.-C.C. Hoarau, D. Hoarau, F. Boury, J.-P. Benoit, and J.-C. Leroux Biomaterials 26 2005 6242
11. J.H. Jung, K. Nakashima, and S. Shinkai Nano Lett. 1 2001 145
12. K. Chen, L. Tang, Y. Xia, and Y. Wang Langmuir 24 2008 13838
13. S. Yagai, T. Nakajima, K. Kishikawa, S. Kohmoto, T. Karatsu, and A. Kitamura J. Am. Chem. Soc. 127 2005 11134
14. Z.M. Yang, P.L. Ho, G.L. Liang, K.H. Chow, Q.G. Wang, Y. Cao, Z.H. Guo, and B. Xu J. Am. Chem. Soc. 129 2007 266
15. J.J.D. de Jong, L.N. Lucas, R.M. Kellogg, J.H.V. Esch, and B.L. Feringa Science 304 2004 278
16. K. Murata, M. Aoki, T. Nishi, A. Ikeda, S. Shinkai, and D.N. Reinhoudt J. Chem. Soc., Chem. Commun. 1991 1715
17. N. Amanokura, Y. Kanekiyo, S. Reinhoudt, and D.N. Shinkai J. Chem. Soc. Perkin Trans. 2 1999 1995
18. T. Ishi-i, J.H. Jung, and S. Shinkai J. Mater. Chem. 10 2000 2238
19. S.-I. Kawano, N. Fujita, and S. Shinkai J. Am. Chem. Soc. 126 2004 8592
20. A. Kishimura, T. Yamashita, and T. Aida J. Am. Chem. Soc. 127 2005 179
21. F. Fages Angew. Chem., Int. Ed. 45 2006 1680
22. T. Tu, W. Assenmacher, H. Peterlik, R. Weisbarth, M. Neiger, and K.H. Dotz Angew. Chem., Int. Ed. 46 2007 6368
23. Q. Liu, Y. Wang, W. Li, and L. Wu Langmuir 23 2007 8217
24. U. Hahn, A.R. Hirst, J.L. Delgado, A. Kaeser, B.D. -Nicot, J.F. Neirengarten, and D.K. Smith Chem. Commun. 2007 4943
25. P. Sahoo, D.K. Kumar, D.R. Trivedi, and P. Dastidar Tetrahedron lett. 49 2008 3052
26. A. Gasnier, G. Royal, and P. Terech Langmuir 25 2009 8751
27. M.-O.M. Piepenbrock, N. Clarke, and J.W. Steed Langmuir 25 2009 8451
28. Y.-R. Liu, L. He, J. Zhang, X. Wang, and C.-Y. Su Chem. Mater. 21 2009 557
29. M.-O.M. Piepenbrock, G.O. Lloyd, N. Clarke, and J.W. Steed Chem. Rev. 110 2010 1960
30. M. Cametti, A.D. Cort, and M. Zinic Chem. Commun. 2007 3535
31. H. Maeda, Y. Haketa, and T. Nakanishi J. Am. Chem. Soc. 129 2007 13661
32. M. Yamanaka, T. Nakamura, T. Nakagawa, and H. Itagaki Tetrahedron Lett. 48 2007 8990
33. C. Wang, D. Zhang, and D. Zhu Langmuir 23 2007 1478
34. H. Yang, T. Yi, Z. Zhou, J. Wu, M. Xu, F. Li, and C. Huang Langmuir 23 2007 8224
35. T.H. Kim, M.S. Choi, W.S. Lyood, and T.S. Lee Chem. Commun. 2008 2364
36. H. Maeda Chem. Eur. J. 14 2008 11274
37. Y.-M. Zhang, Q. Lin, T.-B. Wei, X.-P. Qin, and Y. Li Chem. Commun. 2009 6074
38. M. Teng, G. Kuang, X. Jia, M. Gao, Y. Li, and Y. Wei J. Mater. Chem. 19 2009 5648
39. J.-W. Liu, Y. Yang, C.-F. Chen, and J.-T. Ma Langmuir 26 2010 9040
40. R. Oda, I. Huc, and S.J. Candau Angew. Chem., Int. Ed. 37 1998 2689
41. T. Becker, C.Y. Goh, F. Jones, M.J. Mcildowie, M. Mocerino, and M.I. Ogden Chem. Commun. 2008 3900
42. H. Maeda, R. Fujii, and Y. Haketa Eur. J. Org. Chem. 2010 1469
43. S.Y. Zhang, S.Y. Yang, J.B. Lan, S.J. Yang, and J.S. You Chem. Commun. 2008 6170
44. H. Basit, A. Pal, S. Sen, and S. Bhattacharya Chem. Eur. J. 14 2008 6534
45. A. Pal, H. Basit, S. Sen, V.K. Aswal, and S. Bhattacharya J. Mater. Chem. 19 2009 4325
46. J.-S. Shen, Q.-G. Cai, Y.-B. Jiang, and H.-W. Zhang Chem. Commun. 46 2010 6786
47. G.O. Lloyd, and J.W. Steed Soft Matter 7 2011 75
48. A. Bianchi, K. Bowman-James, and E. Garcia-Espana Supramolecular Chemistry of Anions 1997 Wiley-VCH New York
49. J.L. Sessler, P.A. Gale, and W.-S. Cho Anion Receptor Chemistry 2006 Royal Society of Chemistry Cambridge, UK
50. F.P. Schmidtchen, and M. Berger Chem. Rev. 97 1997 1609
51. P.A. Gale Coord. Chem. Rev 199 2000 181
52. P.D. Beer, and P.A. Gale Angew. Chem., Int. Ed. 40 2001 486
53. P.A. Gale Coord. Chem. Rev. 240 2003 191
54. P.A. Gale Acc. Chem. Res. 39 2006 465
55. P.A. Gale, S.E. Garcia-Garrido, and J. Garric Chem. Soc. Rev. 37 2008 151
56. C. Caltagirone, and P.A. Gale Chem. Soc. Rev. 38 2009 520
57. A.P. Davis Coord. Chem. Rev. 250 2006 2939
58. M. Chahar, S. Upreti, and P.S. Pandey Tetrahedron 63 2007 171
59. V.K. Khatri, M. Chahar, K. Pavani, and P.S. Pandey J. Org. Chem. 72 2007 10224
60. Z. Xu, S.K. Kim, and J. Yoon Chem. Soc. Rev. 39 2010 1457
61. Gale, P., Gunnlaugsson, T., (Eds.), Supramolecular Chemistry of Anionic Species Themed Issue, Chem. Soc. Rev., 2010, 39, 3595.
62. S. Kubik, R. Kirchner, D. Nolting, and J. Seidel J. Am. Chem. Soc. 124 2002 12752
63. C.R. Bondy, P.A. Gale, and S.J. Loeb J. Am. Chem. Soc. 126 2004 5030
64. E.A. Katayev, Y.A. Ustynyuk, and J.L. Sessler Coord. Chem. Rev. 250 2006 3004
65. S.O. Kang, V.W. Day, and K. Bowman-James Org. Lett. 11 2009 3654
66. H.J. Kim, S. Bhuniya, R.K. Mahajan, R. Puri, H. Liu, K.C. Ko, J.Y. Li, and J.S. Kim Chem. Commun. 2009 7128
67. M.T. Huggins, T. Butler, P. Barber, and J. Hunt Chem. Commun. 2009 5254
68. V.K. Khatri, S. Upreti, and P.S. Pandey Org. Lett. 8 2006 1755
69. To a solution of 3α, 12α-bis-{O-(N1-imidazole)acetyl} deoxycholate 1 (100 mg, 0.16 mmol) in dry acetonitrile (80 ml), compound 2a, N,N′-(bromoacetyl)1,3-diaminobenzene (55 mg, 0.16 mmol) dissolved in dry acetonitrile was added. The solution was refluxed for 72 h. After completion of the reaction, the reaction mixture was allowed to cool at room temperature, acetonitrile was evaporated under vacuum completely and the residue obtained was recrystallised from chloroform-hexane to give the pure product 3a as a white solid in 80% yield. The hexafluorophosphate salt of receptor 3a was obtained by the treatment of the bromide salt with a saturated methanolic solution of ammonium hexafluorophosphate.
70. R.S. Coleman, and R.M. Pires Nucleic Acid Res. 25 1997 4771
71. N. Fujita, and S. Shinkai R.G. Weiss, P. Terech, Molecular Gels: Materials with Self-Assembled Fibrillar Networks 2006 Springer The Netherlands Chapter 15
72. J. Peng, K. Liu, J. Liu, Q. Zhang, X. Feng, and Y. Fang Langmuir 24 2008 2992
73. J.H. Jung, Y. Ono, K. Sakurai, M. Sano, and S. Shinkai J. Am. Chem. Soc. 122 2000 8648
74. H.A. Benesi, and J.H. Hilderbrand J. Am. Chem. Soc. 71 1949 2703