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- W1978472443 abstract "Abstract As previous studies in the field of bioorganometallic chemistry have unveiled, metal‐containing analogues of natural products frequently exhibit surprising biological activities. In this context, a synthetic approach to analogues of the eicosanoids 5‐HETE and 8‐HETE possessing a 1,3‐butadiene–Fe(CO) 3 substructure was elaborated. The chosen structures are characterized by a central (2 E ,4 Z )‐hexa‐2,4‐dien‐1‐ol–Fe(CO) 3 moiety (as the potential “metal pharmacophore”) and carry a lipophilic ω‐6‐substituent as well as a hydrophilic α‐side chain (carboxylic acid). Using the cationic complex tricarbonyl[η 5 ‐1‐(methoxycarbonyl)pentadienyl]iron hexafluorophosphate ( rac ‐ 4 ) as a starting material, the synthesis of a simplified Fe(CO) 3 ‐complexed HETE analogue ( rac ‐ 3 ) was achieved by exploiting the addition of an alkynyl Cu species to rac ‐ 4 . The carbon skeleton was completed through diastereo(Ψ‐ exo )selective addition of a titanium–zinc organyl [prepared from ethyl 4‐iodobutyrate, activated Zn powder, and Ti(O i Pr) 3 Cl] as a butyrate D 4 synthon to an aldehyde function by using 2‐Me‐THF as the solvent of choice. The (sensitive) target compound rac ‐ 3 was shown to induce apoptosis at moderate concentrations in cancer cells (BJAB and Nalm‐6)." @default.
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- W1978472443 date "2011-01-12" @default.
- W1978472443 modified "2023-10-14" @default.
- W1978472443 title "Synthesis and First Biological Evaluation of an Iron‐Containing HETE Analogue" @default.
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- W1978472443 doi "https://doi.org/10.1002/ejoc.201001445" @default.
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