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Volumn 4, Issue 19, 2002, Pages 3267-3270

Angiogenesis inhibitor epoxyquinol A: Total synthesis and inhibition of transcription factor NF-κB

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOGENESIS INHIBITOR; EPOXIDE; EPOXYQUINOL A; HYDROQUINONE DERIVATIVE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN;

EID: 0037136468     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026513n     Document Type: Article
Times cited : (76)

References (29)
  • 3
    • 0032421377 scopus 로고    scopus 로고
    • For a review of natural products as angiogenesis inhibitors, see: Paper, D. H. Planta Med. 1998, 64, 686.
    • (1998) Planta Med. , vol.64 , pp. 686
    • Paper, D.H.1
  • 8
    • 0042819251 scopus 로고    scopus 로고
    • note
    • In refs 3 and 4, epoxyquinol and epoxyquinone dimers were referred to as "exo." However, it is more appropriate to refer to the dimers as "endo" with respect to the carbonyl substituent on the 2H-pyran dienophile.
  • 11
    • 0042819250 scopus 로고    scopus 로고
    • f by TLC with the natural compound RK-302 (see Supporting Information)
    • f by TLC with the natural compound RK-302 (see Supporting Information).
  • 12
    • 0042318090 scopus 로고    scopus 로고
    • note
    • Endo quinone dimer 9 was also produced in 67% yield by Dess-Martin periodinane oxidation of 7, followed by treatment with silica gel (Scheme 1). See Supporting Information for details.
  • 13
    • 0036132294 scopus 로고    scopus 로고
    • It is also conceivable that internal hydride transfer of dienal 4 to a quinone epoxide may occur. For a recent example of an internal hydride transfer, see: Szendi, Z.; Forgo, P.; Tasi, G.; Böcskel, Z.; Nyerges, L.; Sweet, F. Steroids 2002, 67, 31.
    • (2002) Steroids , vol.67 , pp. 31
    • Szendi, Z.1    Forgo, P.2    Tasi, G.3    Böcskel, Z.4    Nyerges, L.5    Sweet, F.6
  • 15
    • 0041817209 scopus 로고    scopus 로고
    • 3) analysis of the crude reaction mixture indicates a ratio of dienal 4:2H-pyran 2:dimer 1:dimer 10 of 1:4.9:7.9:7.7
    • 3) analysis of the crude reaction mixture indicates a ratio of dienal 4:2H-pyran 2:dimer 1:dimer 10 of 1:4.9:7.9:7.7.
  • 16
    • 0034583305 scopus 로고    scopus 로고
    • For enhancement of endo/exo selectivity by water in Diels-Alder reactions, see: Otto, S.; Engberts, J. B. F. N. Pure Appl. Chem. 2000, 72, 1365.
    • (2000) Pure Appl. Chem. , vol.72 , pp. 1365
    • Otto, S.1    Engberts, J.B.F.N.2
  • 17
    • 0042819210 scopus 로고    scopus 로고
    • For endo Diels-Alder dimerization of two identical 2H-pyran monomers, see ref 4
    • For endo Diels-Alder dimerization of two identical 2H-pyran monomers, see ref 4.
  • 27
    • 0036217821 scopus 로고    scopus 로고
    • For a review of natural products as modulators of the NF-κB signaling pathway, see: Bremner, P.; Heinrich, M. J. Pharm. Pharmacol. 2002, 54, 453.
    • (2002) J. Pharm. Pharmacol. , vol.54 , pp. 453
    • Bremner, P.1    Heinrich, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.