Biomedical subjects
Publications and source records attributed to Françoise Guéritte.
A new eudesmane derivative, 4alpha,5alpha-dihydroxyeudesma-11(13)-en-12-oic acid, was isolated from Laggera pterodonta. Its structure was elucidated as (1) on the basis of spectroscopic evidence. Moreover, six known compounds were isolated: pterodontriol A (2), pterodontriol B, pterodonta acid (3), ilicic acid (4), costic acid and beta-amyrin. Cytotoxic activity of compounds 2, 3 and 4 was investigated.
Three new eudesmane sesquiterpenes, 5 beta-hydroxyilicic acid (1), 5 alpha-hydroxyl-4-epi-ilicic acid methyl ester (2), and 3 alpha-hydroxyilicic acid (3), together with 12 known sesquiterpenes were isolated from the aerial part of Laggera alata. Their structures were elucidated primarily by NMR and mass spectroscopic methods. The structures of 1 and 2 were confirmed by X-ray crystallography.
The palladium-catalyzed, two-step, one-pot borylation/Suzuki coupling (BSC) reaction was developed to synthesize sterically hindered 2,2'-disubstituted biphenyl and phenyl-indole compounds in a short, simple, and efficient manner from two easily accessible aryl halides. High yields can be obtained by choosing properly both components according to their rough electronic properties. The illustration of the utility of this method was provided by the solution and solid-phase synthesis of seven- or eight-membered biphenyl lactams 5a-e, as well as paullone 3a. These compounds exhibit moderate albeit significant cytotoxicities and may serve as structural models for future medicinal chemistry developments.
An improvement of the synthesis of biphenyl-carbamate 2a, the most active analogue of rhazinilam 1 so far, was performed using the Pd-catalyzed borylation/Suzuki coupling (BSC) method developed in our laboratories. The preparation of A-ring analogues of 2a bearing electron-withdrawing or donating groups is reported according to this new synthetic scheme. The antitubulin properties as well as the cytotoxicity of these compounds toward human cancer cell lines were evaluated in comparison with rhazinilam and 2a.
Phytochemical reinvestigation on Ligularia nelumbifolia afforded four novel sinapyl alcohol analogues named nelumols B-E (1-4) and three known sinapyl alcohol derivatives (5-7). Their structures were elucidated by NMR techniques. Total syntheses of cytotoxic geranyloxy sinapyl alcohol (6) and geranyloxy sinapyl aldehyde (7) were carried out via two different paths. The 4-O-benzyl-substituted analogues (20 and 27) as well as the 4-O-(2-methylbutenyl) derivatives (34 and 35) were also synthesized. The cytotoxicities of 6 and 7 were measured using A-549, HL-60, and KB cancer cell lines.
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