102019-30-7Relevant academic research and scientific papers
Synthetic studies toward c-glucosidic ellagitannins: A biomimetic total synthesis of 5-O-desgalloylepipunicacortein A
Malik, Ga?lle,Natangelo, Anna,Charris, Jaime,Pouységu, Laurent,Manfredini, Stefano,Cavagnat, Dominique,Buffeteau, Thierry,Deffieux, Denis,Quideau, Stéphane
supporting information; experimental part, p. 9063 - 9074 (2012/10/07)
C-glucosidic ellagitannins constitute a subclass of bioactive polyphenolic natural products with strong antioxidant properties, as well as promising antitumoral and antiviral activities that are related to their capacity to interact with both functional and structural proteins. To date, most synthetic efforts toward ellagitannins have concerned glucopyranosic species. The development of a synthetic strategy to access C-glucosidic ellagitannins, whose characteristic structural feature includes an atropoisomeric hexahydroxydiphenoyl (HHDP) or a nonahydroxyterphenoyl (NHTP) unit that is linked to an open-chain glucose core by a C-aryl glucosidic bond, is described herein. The total synthesis of the biarylic HHDP-containing 5-O- desgalloylepipunicacortein A (1 β) was achieved by either using the natural ellagic acid bis-lactone as a precursor of the requested HHDP unit or by implementing an atroposelective intramolecular oxidative biarylic coupling to forge this HHDP unit. Both routes converged in the penultimate step of this synthesis to enable a biomimetic formation of the key C-aryl glucosidic bond in the title compound.
Radiosynthesis of 3-(3-[18F]fluoropropoxy)-4-(benzyloxy)-N-[(1- dimethylaminocyclopentyl)methyl]-5-methoxybenzamide, a potential PET radiotracer for the glycine transporter GlyT-2
Tian, Haibin,Vogel, Rebecca,Amici, Louis,Tamagnan, Gilles,Baldwin, Ronald M.
, p. 1247 - 1258 (2007/10/03)
The recently described selective and potent GlyT2 antagonist, 4-benzyloxy-3, 5-dimethoxy-N-[(1-dimethylaminocyclopentyl) methyl]benzamide (IC50 = 16 nM) provided an important additional tool to further characterize GlyT2 pharmacology. In order to identify an effective PET radioligand for in vivo assessment of the GlyT-2 transporter, 3-(3-[ 18F]fluoropropoxy)-4-(benzyloxy)-N-((1-dimethylaminocyclopentyl) methyl)-5-methoxybenzamide ([18F]3), a novel analog of 4-benzyloxy-3,5-dimethoxy-N-[(1-dimethylaminocyclopentyl) methyl]benzamide was synthesized using a one-pot, two-step method. The NCA radiofluorination of 1,3-propanediol di-p-tosylate in the presence of K2CO3 and Kryptofix-222 in acetonitrile gave 81% 3-[18F]fluoropropyl tosylate, which was subsequently coupled with 4-benzyloxy-3-hydroxy-5-methoxy-N-[(1- dimethylaminocyclopentyl) methyl]-benzamide in the same reaction vessel. Solvent extraction and HPLC (Eclipse XDB-C8 column, 80/20/0.1 MeOH/H 2O/Et3N, 3.0 ml/min) gave [18F]3 in 98.5% radiochemical purity. The radiochemical yield was determined to be 14.0-16.2% at EOS, and the specific activity was 1462 ± 342 GBq/μmol. The time of synthesis and purification was 128 min. The final product was prepared as a sterile saline solution suitable for in vivo use. Copyright
Syntheses of two cytotoxic sinapyl alcohol derivatives and isolation of four new related compounds from Ligularia nelumbifolia
Zhao, Yu,Hao, Xiaojiang,Lu, Wei,Cai, Junchao,Yu, Hong,Sevenet, Thierry,Gueritte, Francoise
, p. 902 - 908 (2007/10/03)
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.
Selective hydroxy group protection of gallic acid
Zhu, Jieping,Chastanet, Jacqueline,Beugelmans, Rene
, p. 2479 - 2486 (2007/10/03)
An efficient procedure allowing selective differentiation of the 4-hydroxy group of methyl gallate was reported.
Studies on the Synthesis of Aryl Ethers Using Arene-Manganese Chemistry
Pearson, Anthony J.,Bruhn, Paul R.
, p. 7092 - 7097 (2007/10/02)
Selective arylation of polyfunctional phenols, using chlorobenzene- and p-chlorotoluene-manganese tricarbonyl cations, is described.The intermediate arene-manganese complexes are found to undergo stereo- and regioselective reactions with Schoellkopf's chiral glycine enolate equivalent to give dienyl-Mn(CO)3 complexes.Treatment of these complexes with N-bromosuccinimide at room temperature, followed by hydrolysis of the dihydropyrazine, gives diaryl ethers in which one of the aromatic rings is an arylglycine methyl ester.
VOM RADIOAKTIVEN CONIFERIN ZUM MARKIERTEN TURGORIN
Schildknecht, Hermann,Milde, Reiner
, p. 23 - 32 (2007/10/02)
The first Periodic Leaf Movement Factor ("PLMF 1"), 4-O-(β-D-glucopyranosyl 6-sulfate)gallic acid (1), which is chemonastically active on Mimosa pudica L., and its (14)C-carboxyl-labelled analog were synthesized by Koenigs-Knorr reaction of a D-glucose derivative with a suitably blocked gallic acid to give 4-O-β-D-glucopyranosylgallic acid after deblocking.Regioselective sulfatation with sulfur trioxide-pyridine afforded 1.The (14)C-labelled analog was prepared via regioselective glucosylation of methyl galloate with 2,3,4,6-tetra-D-acetyl-α-D-glucopyranosyl bromide and subsequent sulfatation of the deblocked glucoside.
