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Volumn 45, Issue 17, 2004, Pages 3359-3362

1,3-Dipolar cycloaddition route to novel isoxazole-type derivatives related to combretastatin A-4

Author keywords

1,3 Dipolar cycloaddition; Combretastatin; Nitrile oxide

Indexed keywords

ALDOXIME; COMBRETASTATIN A4; HETEROCYCLIC COMPOUND; HYPOCHLORITE SODIUM; ISOXAZOLE DERIVATIVE; NITRILE; OXIDE; PHENYL GROUP; STILBENE DERIVATIVE;

EID: 1842637466     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.020     Document Type: Article
Times cited : (33)

References (27)
  • 6
    • 0041421003 scopus 로고    scopus 로고
    • For a review, see:
    • For a review, see: Nam N.-H. Curr. Med. Chem. 10:2003;1697-1722.
    • (2003) Curr. Med. Chem. , vol.10 , pp. 1697-1722
    • Nam, N.-H.1
  • 16
    • 1842629464 scopus 로고    scopus 로고
    • note
    • 3): δ 7.62 (d, 1H, J=15.3 Hz), 6.73 (s, 2H), 6.70 (d, 1H, J=15.3 Hz), 3.89 (s, 6H), 3.87 (s, 3H), 3.49 (q, 4H, J=7.1 Hz), 1.23 (br s, 6H).
  • 22
    • 1842730171 scopus 로고    scopus 로고
    • note
    • 3): δ 7.24 (dd, 1H, J=8.5, 2.1 Hz), 7.07 (d, 1H, J=2.1 Hz), 6.75 (d, 1H, J=8.5 Hz), 6.46 (s, 2H), 5.54 (d, 1H, J=5.7 Hz), 5.05 (d, 1H, J=5.7 Hz), 3.79 (s, 9H), 3.77 (s, 3H), 3.45 (m, 4H), 1.27 (t, 3H, J=7.0 Hz), 1.25 (t, 3H, J=7.0 Hz), 0.92 (s, 9H), 0.05 (s, 3H), 0.02 (s, 3H).
  • 24
    • 1842629463 scopus 로고    scopus 로고
    • note
    • 5,4 is larger for isomer 3f (1.06) than for isomer 4f (0.49).
  • 25
    • 1842680028 scopus 로고    scopus 로고
    • note
    • 13C NMR and mass data. Assessment of their ability to inhibit in vitro polymerization is now under investigation.
  • 26
    • 1842629462 scopus 로고    scopus 로고
    • note
    • 24 With both dipolarophiles investigated, 2a and 2d, coupling was slightly more efficient (respective yields: 46% vs 38%, 11% vs 6%), probably due to a lesser steric hindrance. But the deprotecting step, realized with trifluoroacetic acid, was less effective. At last protection of the phenol function with a silyl group seems more effective.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.