A direct route to biologically active kainic acid analogs

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2314-2315

  Maeda, Hiroshi ^a   Kraus, George A ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; KAINIC ACID DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030917061     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962114s     Document Type: Article

References (14)

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3. Hashimoto, K.; Shirahama, H. Tetrahedron Lett. 1991, 32, 2625. Hashimoto, K.; Horikawa, M.; Ishida, M.; Shinozaki, H.; Shirahama, H. Bioorg. Med. Chem. Lett. 1992, 2, 743. Horikawa, M.; Shirahama, H. Synlett 1996, 95.
4. Hashimoto, K.; Shirahama, H. Tetrahedron Lett. 1991, 32, 2625. Hashimoto, K.; Horikawa, M.; Ishida, M.; Shinozaki, H.; Shirahama, H. Bioorg. Med. Chem. Lett. 1992, 2, 743. Horikawa, M.; Shirahama, H. Synlett 1996, 95.
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8. Brook, M. A.; Seebach, D. Can. J. Chem. 1987, 65, 836. The methylene α to the nitro group in 4 was a doublet rather than two doublets of doublets (a pattern often observed in the syn-isomers).
9. Attempts to convert 4 directly into 7 or the amino diester with hydrogen and Ra-Ni in THF, MeOH, or EtOAc led to mixtures of very polar materials.
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13. Compounds 9 and 10 contain two rotamers in a 1:1 ratio. In 9, the methine proton at C-2 appears as two doublets at 4.13 and 4.17 with J = 5.7 Hz. In 10, the methine proton at C-2 appears as two doublets at 4.62 and 4.65 with J = 7.2 Hz.
14. all-cis-Kainic acid derivatives show anticonvulsant activity: Collins, J. F.; Dixon, A. J.; Badman, G.; De Sarro, G.; Chapman, A. G.; Hart, G. P.; Meldrum, B. S. Neurosci. Lett. 1984, 51, 371.