Synthesis of chirally pure 2,5-disubstituted diketopiperazines derived from trisubstituted phenylalanines

Journal of Heterocyclic Chemistry

Volumn 34, Issue 3, 1997, Pages 835-844

  Danthi, Satyavijayan Narasimhan ^a   Hill, Ronald A ^a  

^a UNIVERSITY OF LOUISIANA AT MONROE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHENYLALANINE DERIVATIVE; PIPERAZINE DERIVATIVE;

ARTICLE; BLOOD BRAIN BARRIER; CHIRALITY; DERIVATIZATION; DRUG SYNTHESIS; HYDROLYSIS; NONHUMAN; STEM CELL; STROKE;

EID: 0030739896     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570340321     Document Type: Article

References (18)

1. W. M. Pardridge, Nutrition and the Brain, Vol 1, R. J. Wurtman and J. J. Wurtman, eds, Raven Press, New York, 1977, pp 141.
2. [2a] R. A. Hill, Ph.D. Dissertation, The Ohio State University, 1991;
3. [b] R. A. Hill, L. J. Wallace, D. D. Miller, H. Tai, R. T. Layer, D. Weinstein, D. L. Willins, and N. J. Uretsky, J. Med. Chem., under revision.
4. A. M. Buchan, H. Lesiuk, K. A. Barnes, H. Li, Z. Huang, K. E. Smith, and D. Xue, Stroke, Supplement I, 24, 1148 (1993).
5. [4a] G. G. C. Hwa and M. Avoli, Exp. Brain. Res., 86, 248, (1991);
6. [b] K. H. McAllister, Eur. J. Pharmacol., 231, 309, (1993).
7. J. M. Witkin, Life Sci., 53, 405 (1993).
8. S. Rajappa and M. V. Natekar, Adv. Heterocyclic Chem., 57, 187 (1993).
9. R. O. Cain and A. E. A. Porter, J. Chem. Soc. Perkin Trans. 1, 3111 (1981).
10. R. B. Baudy, L. P. Greenblatt, I. L. Jirkovsky, M. Conklin, R. J. Russo, D. R. Bramlett, T. A. Emrey, J. T. Simmonds, D. M. Kowal, R. P. Stein, and R. P. Tasse, J. Med. Chem., 36, 331 (1993).
11. H. K. Chenault, J. Dahmer, and G. M. Whitesides, J. Am. Chem. Soc., 111, 6354 (1989).
12. G. Szókán, G. Mezö, and F. Hudecz, J. Chromatogr., 444, 115 (1988).
13. M. Brenner and W. Huber, Helv. Chim. Acta., 36, 1109 (1953).
14. D. E. Nitecki, B. Halpern, and J. W. Westley, J. Org. Chem., 33, 864 (1968).
15. T. Yamazaki, K. Nunami, and M. Goodman, Biopolymers, 31, 1513 (1991).
16. J. L. Kelley, J. A. Linn, and J. W. T. Selway, J. Med. Chem., 32, 1757 (1989).
17. There was racemization observed after 30 days when this compound was stored at room temperature; hence it was stored in a freezer below -5°, whereupon no racemization was observed for at least 3 months.
18. When this compound was stored at room temperature or in a freezer for 30 days, racemization was observed. If stored as a solution in methylene chloride, no racemization was observed for at least 3 months.