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Volumn 71, Issue 10, 2006, Pages 3942-3951

Stereoselective synthesis of 3,6-disubstituted-3,6-dihydropyridin-2-ones as potential diketopiperazine mimetics using organocopper-mediated anti-S N2′ reactions and their use in the preparation of low-molecule CXCR4 antagonists

Author keywords

[No Author keywords available]

Indexed keywords

3,6-DISUBSTITUTED-3,6-DIHYDROPYRIDIN-2-ONES; DIKETOPIPERAZINE MIMETICS; RING-CLOSING METATHESIS; STEREOSELECTIVE SYNTHESIS;

EID: 33646511988     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060390t     Document Type: Article
Times cited : (36)

References (121)
  • 28
    • 0034246704 scopus 로고    scopus 로고
    • (a) Yet, L. Chem. Rev. 2000, 100, 2963.
    • (2000) Chem. Rev. , vol.100 , pp. 2963
    • Yet, L.1
  • 36
    • 33646518845 scopus 로고    scopus 로고
    • Shimohigashi, Y., Ed.; The Japanese Peptide Society: Osaka
    • A portion of this work has appeared in preliminary communications: (a) Niida, A.; Mizumoto, M.; Sasaki, Y.; Tamamura, H.; Otaka, A.; Fujii, N. In Peptide Science; Shimohigashi, Y., Ed.; The Japanese Peptide Society: Osaka, 2004; p 169.
    • (2004) Peptide Science , pp. 169
    • Niida, A.1    Mizumoto, M.2    Sasaki, Y.3    Tamamura, H.4    Otaka, A.5    Fujii, N.6
  • 78
    • 33646512035 scopus 로고    scopus 로고
    • note
    • 1H NMR measurements, upfield shifts of α-protons of 3,6-trans derivatives, which were probably caused by an anisotropic effect of the side-chain phenyl ring, were observed (see the Supporting Information).
  • 97
    • 0003622715 scopus 로고
    • Seminario, J. M., Politzer, P., Eds. Elsevier: New York, (Theoretical and Computational Chemistry)
    • (a) Seminario, J. M., Politzer, P., Eds. Modern Density Functional Theory. A Tool for Chemistry; Elsevier: New York, 1995; Vol. 2 (Theoretical and Computational Chemistry),
    • (1995) Modern Density Functional Theory. A Tool for Chemistry , vol.2
  • 99
    • 33646513998 scopus 로고    scopus 로고
    • note
    • Relative configurations of 48 and 49 were assigned as 3,6-trans derivatives based on the published data (ref 5). The observed chemical shifts of the α-protons of 48 and 49 (2.45 and 2.16 ppm, respectively) were nearly identical to those of the corresponding N-methyl derivatives 27 and 28 (2.41 and 2.14 ppm, respectively). We also confirmed that the α-proton of the corresponding 3,6-cis diastereomer of 48 appeared downfield (3.16 ppm) in comparison with 48, as in the cases of N-methyl derivatives. The α-proton chemical shift of 50 was 2.29 ppm, which is similar to that of the corresponding N-methyl-3,6-trans derivative 30 (2.21 ppm). Based on these data, compound 50 was assigned as 3,6-trans.
  • 113
    • 33646519944 scopus 로고    scopus 로고
    • note
    • 1H NMR experiments, the α-proton of compound 59 was detected at higher field (2.20 ppm) in comparison with that of the corresponding diastereomer (2.72 ppm). This can be rationalized by the anisotropic effect of the naphthalene ring, as in the case of phenylalanine-derived compounds. Based on these data, the relative configuration of 59 was assigned as 3,6-trans. See the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.