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http://dx.doi.org/10.5012/bkcs.2009.30.9.2101

Synthesis of Facial Amphiphile 3,7-Diamino-5α-cholestane Derivatives as a Molecular Receptor  

Ahmad, Md. Wasi (Department of Applied Chemistry, Kyungpook National University)
Jung, Young-Mee (Department of Applied Chemistry, Kyungpook National University)
Khan, Sharaf Nawaz (Department of Applied Chemistry, Kyungpook National University)
Kim, Hong-Seok (Department of Applied Chemistry, Kyungpook National University)
Publication Information
Abstract
A series of facial amphiphiles 3,7-diaminocholestane were synthesized from 3,7-diketocholestane via 2 sequential reductive aminations and anion recognition was evaluated with acetate, chloride, bromide, fluoride and phosphate anions. The stereo-selective reductive amination protocol was utilized to synthesized facial amphiphiles afforded receptors in high yields. The molecular receptor 2 showed the highest binding constant with acetate in a 1:1 ratio.
Keywords
Facial amphiphile; Anion receptor; Reductive amination; Aminosteroids; Stereoselectivity;
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1 Lambert, T. N.; Boon, J. M.; Smith, B. D.; Perez-Payan, M. N.; Davis, A. P. J. Am. Chem. Soc. 2002, 124, 5276   DOI   ScienceOn
2 Ayling, A. J.; Broderick, S.; Clare, J. P.; Davis, A. P.; Perez-Payan, M. N.; Lahtinen, M.; Nissinen, J. J.; Rissanen, K. Chem. Eur. J. 2002, 8, 2197   DOI   ScienceOn
3 Siracusa, L.; Hurley, F. M.; Dresen, S.; Lawless, L. J.; Pérez-Payán, M. N.; Davis, A. P. Org. Lett. 2002, 4, 4639   DOI   ScienceOn
4 Khan, S. N.; Cho, N. J.; Kim, H.-S. Tetrahedron Lett. 2007, 48, 5189   DOI   ScienceOn
5 Khan, S. N.; Jung, Y. M.; Kim, B. J.; Cho, H.; Lee, J.; Kim, H.-S. Bioorg. Med. Chem. Lett. 2008, 18, 2558.   DOI   ScienceOn
6 Khan, S. N.; Bae, S. Y.; Kim, H.-S. Tetrahedron Lett. 2005, 46, 7675   DOI   ScienceOn
7 Khan, S. N.; Cho, N. J.; Kim, H.-S. In Catalyst for the Fine Chemical Synthesis; Robert, S. M.; Whittall, J., Eds.; Regio- and Stereo-Controlled Oxidations and Reductions; John Wiley & Sons: Chichester, 2007; Vol. 5, p 175
8 MP2 calculation at the AM1 mode level was performed SPARTAN'04 for Windows (Wavefunction, Inc.: Irvine, CA)
9 Rehman, A.; Li, C.; Budge, L. P.; Street, S. E.; Savage, P. B. Tetrahedron Lett. 1999, 40, 1865   DOI   ScienceOn
10 Broderick, S.; Davis, A. P.; Williams, R. P. Tetrahedron Lett. 1998, 39, 6083   DOI   ScienceOn
11 Li, C.; Rehman, A.; Dalley, N. K.; Savage, P. B. Tetrahedron Lett. 1999, 40, 1861   DOI   ScienceOn
12 Zhou, X.-T.; Rehman, A.; Li, C.; Savage, P. B. Org. Lett. 2000, 2, 3015   DOI   ScienceOn
13 Clare, J. P.; Ayling, A. J.; Joos, J.-B.; Sission, G. M.; Perez- Payan, M. N.; Lambert, T. N.; Shukla, R.; Smith, B. D.; Davis, A. P. J. Am. Chem. Soc. 2005, 127, 10739   DOI   ScienceOn
14 Bhattarai, K. M.; del Amo, V.; Magro, G.; Sission, A. L.; Joos, J.-B.; Charmant, J. P. H.; Kantacha, A.; Davis, A. P. Chem. Commun. 2006, 2335
15 Rivera, D. G.; Concepcion, O.; Perez-Labrada, K.; Coll, F. Tetrahedron 2008, 64, 5298   DOI   ScienceOn
16 McNally, B. A.; Koulov, A. V.; Smith, B. D.; Joos, J. B.; Davis, A. P. Chem. Commun. 2005, 1087
17 del Amo, V.; Siracusa, L.; Markidis, T.; Baragaña, B.; Bhattarai, K. M.; Galobardes, M.; Naredo, G.; Perez-Payan, M. N.; Davis, A. P. Org. Biomol. Chem. 2004, 2, 3320   DOI   ScienceOn
18 Koulov, A. V.; Lambert, T. N.; Jain, M.; Boon, J. M.; Smith, B. D.; Li, H. Y.; Sheppard, D. N.; Joos, J. B.; Clare, J. P.; Davis, A. P. Angew. Chem. Int. Ed. 2003, 42, 4931   DOI   ScienceOn
19 Li, C.; Peters, A. S.; Meredith, E. L.; Allman, G. W.; Savage, P. B. J. Am. Chem. Soc. 1998, 120, 2962
20 Bhattacharjya, S.; David, S. A.; Mathan, V. I.; Balaram, P. Biopolymers 1997, 41, 251   DOI   ScienceOn
21 Bruch, M. D.; Cajal, Y.; Koh, J. T.; Jain, M. K. J. Am. Chem. Soc. 1999, 121, 11993   DOI   ScienceOn
22 Hancock, R. E. W. Annu. Rev. Microbiol. 1984, 38, 237   DOI   ScienceOn
23 Guan, Q.; Li, C.; Schmidt, E. J.; Boswell, J. S.; Walsh, J. P.; Allman, G. W.; Savage, P. B. Org. Lett. 2000, 2, 2837   DOI   ScienceOn
24 Li, C.; Budge, L. P.; Driscoll, C. D.; Willardson, B. M.; Allman, G. W.; Savage, P. B. J. Am. Chem. Soc. 1999, 121, 931   DOI   ScienceOn
25 Ding, B.; Guan, Q.; Walsh, J. P.; Boswell, J. S.; Winter, T. W.; Winter, E. S.; Boyd, S. S.; Li, C.; Savage, P. B. J. Med. Chem. 2002, 45, 663   DOI   ScienceOn