Synthesis of 3-hydroxylated analogues of D-aspartic acid β-hydroxamate

Synthetic Communications

Volumn 27, Issue 3, 1997, Pages 395-403

  Charvillon, F Burgat ^a   Amouroux, R ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYASPARTIC ACID BETA HYDROXAMIC ACID; ASPARTIC ACID BETA HYDROXAMIC ACID; ASPARTIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHIRALITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TUMOR CELL;

EID: 0342785216     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708006039     Document Type: Article

References (17)

1. a) Thomasset, N.; Hamedi-Sangsari, F.; Tournaire, R.; Navarro, C.; Malley, S.; Goetsch, L.; Grange, J.; Vila. J. Int. J. Cancer 1991, 49, 421.
2. b) Tournaire, R.; Malley, S.; Hamedi-Sangsari, F.; Thomasset, N.; Grange, J.; Doré, J. F.; Vila, J. Int. J. Cancer 1994, 58, 420.
3. c) Malley, S.; Grange, J.; Hamedi-Sangsari, F.; Vila, J. Proc. Natl. Acad. Sci. USA 1994, 91, 11017.
4. LAH (L isomer of DAH) showed comparable activities to those of DAH but was more toxic.Thus, D configuration is maintained for analogues.
5. a) Saito, S.; Bunya, N.; Inaba, M.; Moriwake, T.; Torii, S. Tetrahedron Lett. 1985, 26, 5309.
6. b) Legters, J.; Thijs, L.; Zwanenburg, B. Tetrahedron 1991, 47, 5287.
7. c) Hansson, T. G.; Kihlberg, J. O. J. Org. Chem. 1986, 51, 4490.
8. d) Wagner, R.; Tilley, J. W.; Lovey, K. Synthesis 1990, 785.
9. e) Gao, Y.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 7538.
10. f) Lohray, B. B.; Ahuja, J. R. J. Chem. Soc., Chem. Com. 1990, 95.
11. a) Javier Sardina, F.; Paz, M. M.; Fernandez-Megia, E.; F. de Boer, R.; Pilar Alvarez, M. Tetrahedron Lett. 1992, 33, 4637.
12. b) Palomo, C.; Cabré, F.; Ontaria, J. M. Tetrahedron Lett. 1992, 33, 4819.
13. Mori, K.; Iwasawa, H. Tetrahedron 1980, 36, 87.
14. Kaneko, T.; Katsura, H. Bull. Chem. Soc. Japan 1963, 36, 899.
15. De Groot, N.; Lichtenstein, N. Bull. Research Council Israël 1959, 116.
16. 2OH ratio is too high (a 3/4 ratio is a good compromise). On the other hand, the N-hydroxysuccinimide derivative i was isolated if this ratio is two low. The role of NaOH and the mechanism of the transformations of diesters into monohydroxamates are under study. (Equation Presented)
17. Mattingly, P. G.; Miller, M. J.; Cooper, R. D. G.; Daugherty, B. W. J. Org. Chem. 1983, 48, 3556.