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Volumn 46, Issue 7, 2003, Pages 1180-1190

Modes of methyleneoxy bridging and their effect on tetrahydronaphthalene lignan cytotoxicity

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA CONIDENDRIN; BENZODIHYDROPYRAN DERIVATIVE; CYTOTOXIC AGENT; DIOXATRICYCLODECANE DERIVATIVE; LIGNAN DERIVATIVE; OXABICYCLOOCTANE DERIVATIVE; PODOPHYLLOTOXIN; SIKKIMOTOXIN; TETRALIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037468899     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020158p     Document Type: Article
Times cited : (13)

References (18)
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  • 2
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    • Directed DDQ-promoted benzylic oxygenations of tetrahydronaphthalenes
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  • 3
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    • note
    • One indicator of the spacial relation between fused and pendant aromatic ring is the torsion angle C-5, C-4a, C-4, all within the tetrahydronaphthalene scaffold, and C-1′ of the pendant ring. The measure of this torsion angle indicates the position of C-1′ relative to the plane of the fused aromatic ring. The energy-minimized, Alchemy models of oxolane 10 and oxabicyclooctane 5 (Scheme 1) and dioxatricyclodecane 14 and oxabicyclooctane 16 (Scheme 2) have the torsion angles as follows: 10, 73.6°; 5, 24.6°; 14, 26.1°; and 16, 48.9°. The torsion angle C-4a, C-4, C-1′, and C-2′(or 6′) defines the twist orientation of the pendant ring plane relative to the plane of the fused aromatic ring.
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    • The naturally occurring lignans
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  • 6
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    • note
    • A shorter route to 28, involving initial mesylation of oxabicyclooctane 6 followed by reduction, was infeasible since the mesylate of 6 was found unstable at temperatures considerably lower than that required for a NaI/Zn-reduction.
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    • note
    • Preliminary investigations by Dr. Susan Bane (Chemistry Department, SUNY Binghamton, Binghamton, NY) indicate that unlike PT its cytotoxic dioxatricyclodecane derivative 14 has no effect on microtubule polymerization at concentrations up to 55 μM.
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    • note
    • Tripos Inc, 1699 South Hanley Road, St. Louis, MO 63144.
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    • Some constituents of Australobaileya scandens (Austrobailyaceae) structures of seven new lignans
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    • Anti-tumor agents. I. DNA topoisomerase II inhibitory activity and the structural relationship of podophyllotoxin derivatives as antitumor agents
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.