61621-83-8Relevant academic research and scientific papers
New cytotoxic bis 5-alkylresorcinol derivatives from the leaves of Oncostemon bojerianum from the Madagascar rainforest
Chaturvedula, V. S. Prakash,Schilling, Jennifer K.,Miller, James S.,Andriantsiferana, Rabodo,Rasamison, Vincent E.,Kingston, David G. I.
, p. 1627 - 1632 (2002)
Bioassay-directed fractionation of a CH2Cl2-MeOH extract of the leaves of Oncostemon bojerianum resulted in the isolation of eight new 5-alkylresorcinols, named oncostemonols A-H (1-8), and two known derivatives, (8′Z)-1,3-dihydroxy-5-[16′-(3′′, 5′′-dihydroxyphenyl)-8′-hexadecen-1′-yl] benzene (9) and (8′Z)-1,3-dihydroxy-5-[14′-(3′′, 5′′-dihydroxyphenyl)-8′-tetradecen-1′-yl] benzene (10). The structures of the new compounds 1-8 were elucidated on the basis of extensive 1D and 2D NMR spectroscopic interpretation and chemical derivatization. All the compounds exhibited cytotoxic activity against the A2780 ovarian cancer cell line.
Shortcut syntheses of naturally occurring 5-alkylresorcinols with DNA-cleaving properties
Fuerstner,Seidel
, p. 2332 - 2336 (2007/10/03)
Resorcinols such as 1-5 bearing long alkyl- or alkenyl substituents at the C-5 position, including bola-formed bis-resorcinol derivatives, have recently been isolated from natural sources and were shown to exhibit exceptional DNA-cleaving properties under oxidative conditions. Previous synthetic approaches to such compounds seem inappropriately lengthy with regard to their structural simplicity. Disclosed is a very flexible synthesis which assembles these targets from triflate 7 and well accessible alkenes, dienes, enynes, or dienynes, respectively, by means of a boron-mediated reaction manifold. As a typical example, hexadeca-1,15-dien-8-yne 11 is hydroborated with 9-H-9-BBN at all possible sites, the alkenyl borane entity of the resulting tris-borane 12 is selectively cleaved off to afford the desired (Z)-alkene group in a stereoselective manner, the remaining two terminal alkylboranes are treated with NaOMe, and the bis-borate complex 13 thus formed is finally used as the nucleophile for a palladium-catalyzed Suzuki cross-coupling reaction with triflate 7. This sequence is carried out in one pot and provides product 14 in 62% overall yield. Demethylation of 14 (and analogues) can be conveniently achieved by means of 9-iodo-9-BBN to afford the natural product 5. The efficiency and flexibility of this unprecedented approach which combines different features of classical and modern boron chemistry is further demonstrated by the synthesis of anacardic and ginkgolic acid derivatives.
5-Alkylresorcinols from Hakea trifurcata that cleave DNA
Lytollis, William,Scannell, Ralph T.,An, Haoyun,Murty,Reddy, K. Sambi,Barr, John R.,Hecht, Sidney M.
, p. 12683 - 12690 (2007/10/03)
A dichloromethane extract of Hakea trifurcata that mediated relaxation of ?X174 replicative form DNA at micromolar concentrations in the presence of Cu2+ was resolved into six active components by bioassay-guided fractionation. Five of the acti
