Cover Image

NMR Investigation of the complexation of (S)-2-isopropyl- 1-(o-nitrophenyl)sulfonyl)aziridine with ï¢-cyclodextrin

Assia Keniche, Mohamed Z. Slimani, Jose I. Miranda, Jesus M. Aizpurua, Joseph Kajima Mulengi

Abstract


 Aziridines are known to undergo hydrolysis in the presence of cyclodextrins, whereas the latter are largely investigated as potential vectors of biologically active compounds. Despite this easy cyclodextrin-induced cleavage of aziridines in aqueous medium, it was of interest to find out a model aziridine derivative that would be sufficiently water-stable and form a stable complex with b-cyclodextrin in aqueous medium, so that it could be used as a reference in future formulations or vectorization work. Among compounds we have investigated, we found out that only (S)-2-isopropyl-1-(o-nitrophenyl)sulfonyl)aziridine complied with the above-mentioned solubility and stability requirements. NMR studies of the inclusion complex of this derivative with b-cyclodextrin provided useful parameters related to the stoichiometry of the complex and the association constant Ka. The geometry of the complex was assessed by 2D-ROESY experiments, suggesting a deep insertion of the aziridine into the cavity of b-cyclodextrin.


Full Text:

PDF

References


- (a) J. Szejtli J. Chem. Rev., 1998, 98, 1743-1753.

(b) M. Schirra, G. Delogu, P. Cabras, A. Angioni, G. D’Hallewin, A. Veyrat, J. Agric. Food Chem., 2002, 50, 6790-6797.

- M. E. Davis, M.E. Brewster, Nature Rev. Drug Discov., 2004, 3, 1023-1035

- A. A. Desai, H. Ren, M. Mukherjee, W. D. Wulff, Org. Process Res. Dev., 2011, 15, 1108-1115.

- A. Keniche, A. Mezrai, J. Kajima Mulengi, The Open Conf. Proceed., J. 2011, 2, 28-35.

- (a) D. Kurmich, J. R. Regan, D. Disalvo PCT Int. Appl., 2009. WO 2009015067 A2 20090129. US20100048950. Application Number: 12/521005/ Publication: 02/25/2010

(b) M. D’hoodge, I. Kerkaert, M. Rottiers, N. De Kimpe Tetrahedron, 2004, 60, 3637-3641.

- (a) J. Farras, X. Giniesta, P. W. Sutton, J. Taltavull, F. Egeler, P. Romea, F. Urpi, J. Vilarrasa Tetrahedron, 2001, 57, 7665-7674.

(b) B. Moon, S. Mog So, H. Jin Choi Org. Lett., 2002, 4, 949-952.

(c) F. Crestey, M. Witt, K. Frydenvang, D. Stærk, J. W. Joroszewsky, H. Franzyk, J. Org. Chem., 2008, 73, 3566-3569.

(d) B. M. Chanda, R. Vyas, A. Bedekar J. Org. Chem., 2001, 66, 30-34.

- (a) H. Xu, H. Tian, L. Zheng, Q. Liu, L. Wang, S. Zhang Tetrahedron Lett., 2011, 52, 2873-2875.

(b) H. Rubin, J. Cockrell, J. B. Morgan, J. Org. Chem., 2013, 78, 8865-8871.

- (a) V. G. Nenajdenko, A. S. Karpov, E. S. Balenkova Tetrahedron Asymmetry, 2001, 12, 2517-2527.

(b) M. Cernerud, H. Adolfsson, C. Moberg, Tetrahedron Asymmetry, 1997, 8, 2665-2662.

(c) L. W. Bieber, M. C. F. Araujo, Molecules, 2002, 7, 902-906.

- J. Bornholdt, J. Felding, R. P. Rasmus, J. L. Kristensen, Chemistry, A European J., 2010, 16, 12474-12480.

- (a) H-L. Kwong, D. Liu, K-Y. Chan, C-S. Lee, K-H. Huang, C-M. Che Tetrahedron Lett., 2004, 45, 3965-3968.

(b) H. Kawabata, K. Omura, T. Katsuki, Tetrahedron Lett., 2006, 47, 1571-1574.

- L. Fielding, Tetrahedron, 2000, 56, 6151-6170.

- W. Medjahed, A. Tabet Zatla, J. Kajima Mulengi, F. Z. Baba Ahmed, H. Merzouk, Tetrahedron Lett., 2004, 45, 1211-1213.

- (a) S. Mashood Ali, K. Fatma, S. Dhokale, Beilstein J. Org. Chem., 2013, 9, 1917-1924

(b) R. Singh, B. Nitin, M. Jyotsana, S. N. Hiremath J. Pharm. Sciences 2010, 2, 171-183

- K. Surendra, N. Srilakshmi Krishnaveni, M. Arjun Reddy, Y. V. D. Nageswar, K. Rama Rao J. Org. Chem., 2003, 68, 9119-9121.

- (a) B. Srinivas, V. Pavan Kumar, R. Sridhar, K. Surendra, Y. V. D. Nageswar, K. Rama Rao, J. Mol. Catal. A: Chem., 2007, 261, 1-5.

(b) M. Somi Reddy, M. Narender, Y. V. D. Nageswar, K. Rama Rao, Tetrahedron Lett., 2005, 46, 6437-6439.

- G. Maatz, A. Maciollek, H. Ritter Beilstein J. Org. Chem., 2012, 8, 1929-1935

- J. H. Beijnen, S. C. van der Schoot, B. Nuijen, F. M. Flesch, A. Gore, D. Mirjovsky, L. Lenaz, Drug Devel.Indus.Pharm, 2008, 34, 1130-1139.

- K. S. Cameron, D. Fletcher, L. Fielding, Magn. Reson. Chem. 2002, 40, 251-260.

- P. Job, Ann. Chim. 1928, 9, 113-203.

- P. Job, Compt. Rend. Acad. Sci. Paris 1925, 180, 928-930.

- L. Fielding, S. McKellar, J. F. Alastair, Magn. Reson. Chem. 2011, 49, 405-412.

- (a) S. M. Ali, S. K. Upadhyay, Magn. Reson. Chem., 2008, 46, 676-679;

(b) G. Wenz, Beilstein J. Org. Chem. 2012, 8, 1890-1895.

- N. Funasaki, S. Ishikawa, S. Neya, J. Phys. Chem. B, 2003, 107, 10094-10099.

- K. Hirose, J. Incl. Phenom. Macrocycl. Chem. 2001, 39, 193-209.

- (a) H. A. Benesi, J. H. Hildebrand, J. Am Chem. Soc. 1949, 71, 2703-2707.

(b) M. W. Hanna, A. L. Ashbaugh, J. Phys. Chem. 1964, 68, 811-816.

- R. Foster, C. A. Fyfe, Trans. Faraday Soc., 1965, 61, 1626-1631.

- R. Foster, C. A. Fyfe, J. Chem. Soc., Chem. Commun. 1965, 642.

- R. L. Scott, Rec. Trav. Chim. Pays-Bas 1956, 75, 787-789.

- G. Scatchard, Ann. N. Y. Acad. Sci. 1949, 51, 660-672.

- N. J. Rose, R. S. Drago, J. Am. Chem. Soc. 1959, 81, 6138-6141.

- D. Salvatierra, C. Díez, C. Jaime, J. Incl. Phenom., 1997, 27, 215-231.

- A. Bax, D. G. Davies, J. Magn. Reson., 1985, 65, 355-360.

- V. Laine, A. Coste-Sarguet, A. Gadelle, J. Defaye, B. Perly, F. Djedaïni-Pilard, J. Chem. Soc. Perkin Trans, 1995, 2, 1479-1481.

- F. Djedaïni-Pilard, N. Azaroual-Bellanger, M. Gosnat, D. Vernet, B. Perly, J. Chem. Soc. Perkin Trans, 1995, 2, 723-730.

- C. Pean, C. Créminon, J. Grassi, P. Pradelles, B. Perly, F. Djedaïni-Pillard, J. Incl. Phenom. Macrocycl. Chem,. 1999, 33, 307-319.




DOI: http://dx.doi.org/10.13171/mjc.2.5.2013.01.12.23

Refbacks

  • There are currently no refbacks.


Copyright (c) 2015 Mediterranean Journal of Chemistry