Synthesis and enantiomeric separation of 2-phthalimidino-glutaric acid analogues: Potent inhibitors of tumor metastasis [2]

Journal of Medicinal Chemistry

Volumn 42, Issue 16, 1999, Pages 3014-3017

  Shah, Jamshed H ^a   Swartz, Glenn M ^a   Papathanassiu, Adonia E ^a   Treston, Anthony M ^a   Fogler, William E ^a   Madsen, John W ^a   Green, Shawn J ^a  

^a ENTREMED INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHTHALIMIDINO GLUTARIC ACID; THALIDOMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTINEOPLASTIC ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; LETTER; MELANOMA; METASTASIS; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; DRUG SCREENING ASSAYS, ANTITUMOR; GLUTARATES; INDOLES; LUNG NEOPLASMS; MELANOMA, EXPERIMENTAL; MICE; MICE, INBRED C57BL; NEOPLASM TRANSPLANTATION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; THALIDOMIDE;

EID: 0033549894     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990083y     Document Type: Letter

References (22)

1. Cahen, R. L. Evaluation of the teratogenicity of drugs. Clin. Pharmacol. Ther. 1964, 5, 480-514.
2. Bazzoli, A. S.; Manson, J.; Scott, W. J.; Wilson, J. G. The effects of thalidomide and two analogues on the regenerating forelimb of the newt. J. Embryol. Exp. Morph. 1977, 41, 125-135.
3. Sampaio, E. P.; Sarno, E. N.; Gallily, R.; Cohn, Z. A.; Kaplan, G. Thalidomide selectively inhibits tumor necrosis factor α production by stimulated human monocytes. J. Exp. Med. 1991, 173, 699-703.
4. D'Amato, R. J.; Loughnan, M. S.; Flynn, E.; Folkman, J. Thalidomide is an inhibitor of angiogenesis. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 4082-4085.
5. Minchinton, A. I.; Fryer, K. H.; Wendt, K. R.; Clow, K. A.; Hayes, M. M. The effect of thalidomide on experimental tumors and metastases. Anti-Cancer Drugs 1996, 7, 339-343.
6. Helm, F.-Ch.; Frankus, E.; Graudums, I.; Flohe, L. Comparative teratological investigation of compounds structurally and pharmacologically related to thalidomide. Drugs Res. 1981, 31, 941-949.
7. Miyachi, H.; Azuma, A.; Ogasawara, A.; Uchimura, E.; Watanabe, N.; Kobayashi, Y.; Kato, F.; Kato, M.; Hashimoto, Y. Novel biological response modifiers: Phthalimides with tumor necrosis factor-α production-regulating activity. J. Med. Chem. 1997, 40 (18), 2858-2865.
8. Corral, L. G.; Kaplan, G.; Stirling, D.; Wu, M.; Chen, Y.; Moriera, A. L.; Muller, G. W. Selection of novel analogs of thalidomide with enhanced tumor necrosis factor-α inhibitory activity. Mol. Med. 1996, 2 (4), 506-515.
9. Shannon, E. J.; Sandoval, F.; Krahenbuhl, J. L. Hydrolysis of thalidomide abrogates its ability to enhance mononuclear cell synthesis of IL-2 as well as its ability to suppress the synthesis of TNF-α. Immunopharmacology 1996, 990.
10. Nicolson, G. L.; Brunson, K. W.; Fidler, I. J. Specificity of arrest, survival, and growth of selected metastatic variant cell lines. Cancer Res. 1978, 38, 4105-4111.
11. Hart, I. R. The selection and characterization of an invasive variant of the B16 melanoma. Am. J. Pathol. 1979, 97, 587-600.
12. Braun, A. G.; Weinreb, S. L. Teratogen metabolism: spontaneous decay products of thalidomide and thalidomide analogues are not bioactivated by liver microsomes. Teratog. Carcinog. Mutagen. 1985, 5, 149-158.
13. Bauer, K. S.; Dixon, S. C.; Figg, W. D. Inhibition of angiogenesis by thalidomide requires metabolic activation, which is species-dependent. Biochem. Pharmacol. 1998, 55 (11), 1827-1834.
14. Schmahl, H.-J.; Heger, W.; Nau, H. The enantiomers of the teratogenic analog EM12. Toxicol. Lett. 1989, 45, 23-33.
15. Kenyon, B. M.; Browne, F.; D'Amato, R. J. Effects of thalidomide and related metabolites in a mouse cornea model of neovascularization. Exp. Eye Res. 1997, 64 (6), 971-978.
16. Heger, W.; Schmahl, H. J.; Klug, S.; Felies, A.; Nau, H.; Merker, H. J.; Neubert, D. Embryotoxic effects of thalidomide derivatives in the non-human primate callithrix jacchus. IV. Teratogenicity of micrograms/kg doses of the EM12 enantiomers. Teratog. Carcinog. Mutagen. 1994, 14, 115-122.
17. Muller, G. W.; Corral, L. G.; Shire, M. G.; Wang, H.; Moreira, A.; Kaplan, G.; Stirling, D. I. Structural modifications of thalidomide produce analogs with enhanced tumor necrosis factor inhibitory activity. J. Med. Chem. 1996, 39, 3238-3240.
18. Gordon, G. B.; Spielberg, S. P.; Blake, D. A.; Balassubramanian, V. Thalidomide teratogenesis: evidence for a toxic arene oxide metabolite. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 2545-2548.
19. Post, G.; Doll, J.; Hart, I. R.; Fidler, I. J. In vitro selection of murine B16 melanoma varients with enhanced tissue-invasive properties. Cancer Res. 1980, 40, 1636-44.
20. Kenyon, B. M.; Browne, F.; D'Amato, R. J. Effects of thalidomide and related metabolites in a mouse corneal model of neovascularization. Exp. Eye Res. 1997, 64, 971-978.
21. Shimazawa, R.; Miyachi, H.; Takayama, H.; Kuroda, K.; Kato, F.; Kato, M.; Hashimoto, Y. Antiangiogenic activity of tumor necrosis factor-a production regulators derived from thalidomide. Biol. Pharm. Bull. 1999, 22, 224-226.
22. Stirling, D.; Sherman, M.; Strauss, S. Thlidomide. A surprising recovery. J. Am. Pharm. Assoc. 1997, 37, 306-13.