Results 111 to 120 of about 276 (135)
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Stereoselective Synthesis of the C1–C29 Part of Amphidinol 3
The Journal of Organic Chemistry, 2015Stereoselective synthesis of the C1-C29 part of amphidinol 3 (AM3) was achieved. The C1-C20 part was assembled from three building blocks via regioselective cross metathesis to form the C4-C5 double bond and addition of an alkenyllithium and a lithium acetylide to two Weinreb amides followed by asymmetric reduction to form the C9-C10 and C14-C15 bonds,
Takeshi, Tsuruda +3 more
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Effects of lipid constituents on membrane-permeabilizing activity of amphidinols
Bioorganic & Medicinal Chemistry, 2008Amphidinols (AMs) are a new class of polyhydroxyl polyene compounds with potent antifungal activity. Membrane-permeabilizing activities of AM2, AM3, and AM6 were examined using fluorescent-dye leakage experiments with various phosphatidylcholines (PCs) and sterols. All the AMs tested showed the potent activity to cholesterol-containing liposomes.
Nagy, Morsy +5 more
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Structure of Membrane-Bound Amphidinol 3 in Isotropic Small Bicelles
Organic Letters, 2008Amphidinol 3 (AM3) exhibits a potent membrane permeabilizing activity by forming pores in biological membranes. We examined the conformation and location of AM3 using isotropic bicelles, a more natural membrane model than micelles. The results show that AM3 takes turn structures at the two tetrahydropyran rings.
Toshihiro, Houdai +2 more
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Synthesis and Structure Revision of the C43–C67 Part of Amphidinol 3
Organic Letters, 2013Stereoselective synthesis of the C43-C67 part of amphidinol 3 (AM3) and its C51-epimer was achieved starting from a common intermediate corresponding to the tetrahydropyran moiety of AM3, via asymmetric oxidations and Julia-Kocienski olefination. By comparing NMR data of the synthetic specimens with those of AM3, the absolute configuration at C51 of ...
Makoto, Ebine +7 more
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Efficient Syntheses of the Polyene Fragments Present in Amphidinols
Synlett, 2007The C53-C67 and C53-C65 polyene fragments of amphidinols have been synthesized in an efficient and convergent fashion from sorbic acid in good overall yields (30-31%) by employing a chemoselective cross-metathesis of a Weinreb amide and a Julia-Kocienski olefination as the key steps.
Janine Cossy +7 more
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Isolation, structural determination and synthetic approaches toward amphidinol 3
Natural Product Reports, 2014This review highlights the isolation and the structural determination of amphidinol 3 (AM3), as well as the synthetic efforts to its preparation. The mechanism of action of AM3 will not be developed herein.
Charlélie, Bensoussan +5 more
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Diastereoselective synthesis of the C14–C29 fragment of amphidinol 3
Organic & Biomolecular Chemistry, 2013An efficient stereoselective synthesis of the C14–C29 fragment highlighting a coupling reaction between a 1,3-dithiane derivative and an α-branched aldehyde was realized. This highly convergent synthesis involved two chiral pools, L-malic acid and (+)-camphorsulfonic acid, which are the starting compounds to control the six stereogenic centers present ...
Rival, Nicolas +5 more
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Stereoselective Synthesis of the C31−C40/C43−C52 Unit of Amphidinol 3
The Journal of Organic Chemistry, 2009A concise synthesis of a tetrahydropyran ring system corresponding to the C31-C40 and C43-C52 units of amphidinol 3 is described. Successive chemoselective reactions, i.e., cross-metathesis to differentiate the iodoolefin from the terminal olefin and Sharpless asymmetric dihydroxylation on the resulting E-olefin, resulted in expeditious synthesis of an
Mitsunori, Kanemoto +2 more
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Development of an Access Route to the C31−C52 Central Core of Amphidinol 3
Organic Letters, 2007[reaction: see text] An asymmetric synthesis of the heavily oxygenated inner sector of amphidinol 3 constituted of C31-C52 is described. The successful pathway highlights construction of the pair of identical tetrahydropyran subunits from a common intermediate.
Matthew W, Bedore +2 more
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Toxicon, 2007
The cytotoxicity of lingshuiol, a novel polyhydroxy compound with a linear carbon-chain isolated from the cultured marine dinoflagellate Amphidinium sp., and that of amphidinol 2 (AM2) was compared with hepatocytes. Both lingshuiol and AM2 were toxic to primary rat hepatocytes with IC(50) values of 0.21 and 6.4muM, respectively.
Xin-Ming, Qi +5 more
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The cytotoxicity of lingshuiol, a novel polyhydroxy compound with a linear carbon-chain isolated from the cultured marine dinoflagellate Amphidinium sp., and that of amphidinol 2 (AM2) was compared with hepatocytes. Both lingshuiol and AM2 were toxic to primary rat hepatocytes with IC(50) values of 0.21 and 6.4muM, respectively.
Xin-Ming, Qi +5 more
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