The synthesis of enantiomers of an amidic modulator of cancer multidrug resistance, the chirality of which is not prone to chromatography, has been carried out via formation of the diastereoisomeric esters of the precursor racemic acid with (S)-lactamide and separation of the esters on silica gel.
Reversal of Multidrug Resistance in Cancer, ed. KellenJ.A., CRC Press, Boca Raton, 1994; T. Litman, T.E. Druley, W.D. Stein and S.E. Bates, Cell. Mol. Life Sci., 2001, 58, 931.
2.
WeiseM., and PajevaI. K., Curr. Med. Chem., 2001, 8, 685; H.L. Pearce, A. Safa, N. Bach, M. Winter, M. Cirtain and W.T. Beck, Proc. Natl. Acad. Sci. USA, 1989, 86, 5128; T. Suzuki, N. Fukazawa, K. San-nohe, W. Sato, O. Yano and T. Tsuruo, J. Med. Chem., 1997, 40, 2047; B. Iyengar, R. Dorr, D. Alberts, E. Hersh, S. Salmon and W. Remers, J. Med. Chem., 1999, 42, 510.
3.
(a) RosF., GarcíaR., GallegoP., Rivera-FillatM. P., GonzálezM. A., and Grau-OlieteM. R., Pharmazie, 1994, 49, 778; (b) F. Ros, R. García, M.P. Rivera-Fillat, M.A. González and M.R. Grau-Oliete, Arch. Pharm. (Weinheim), 1995, 328, 755; (c) F. Ros, R. García, P. Gallego, A. Sánchez-Caballero, M.P. Rivera-Fillat and M.R. Grau-Oliete, Arch. Pharm. Pharm. Med. Chem., 2000, 333, 329.
4.
RosF., Formation of Branched-off Carbon Backbones by Alkylation of α-Nitro and α-Cyano Carbanions with Tertiary a-Halo Ketones, Esters, and Nitriles. Physicochemical Characteristics and Biological Capabilities of Branched-Chain Compounds, in Recent Res. Dev. Org. Chem., ed. PandalaiS.G., Transworld Research Network, Trivandrum, 2001, vol. 5, pp. 15–25; F. Ros, J. Chem. Res. (S), 2000, 124.
5.
CollinsA.N., SheldrakeG. N., and CrosbyJ., Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds, Chichester, Wiley, 1992; K. William and E. Lee, Drugs, 1985, 30, 333.
6.
BoyleP.H., Quart. Rev., 1971, 25, 323; A.G. Brook, J. Am. Chem. Soc., 1963, 85, 3051; E.J. Eisenbraun, G.H. Adolphen, K.S. Schorno and R.N. Morris, J. Org. Chem., 1971, 36, 414; A. Allen and O. Schnepp, J. Chem. Phys., 1973, 59, 4547; M. Ihara, M. Takahashi, N. Tanaguchi, K. Fukumoto and T. Kametani, J. Chem. Soc., Chem. Commun., 1987, 619; T. Hudlicky, L. Radesca and H.L. Rigbby, J. Org. Chem., 1987, 52, 4397.
7.
JohnsonE.L., and StevensonR., Basic Liquid Chromatography, Varian, Palo Alto, 1978.
8.
JacquesJ., ColletA., and WilenS. H., Enantiomers, Racemates, and Resolutions, Krieger, Malabar, 1994; F. Ros and M.T. Molina, Eur. J. Org. Chem., 1999, 3179; M.V. Roux, P. Jiménez, A. Vacas, F.H. Cano, M.C. Apreda-Rojas and F. Ros, Eur. J. Org. Chem., 2003, 2084.
9.
DavisR.B., and PizziniL., J. Org. Chem., 1960, 25, 1884.