16054-77-6Relevant academic research and scientific papers
PROCESSES FOR PREPARING 2-DIHALO RIBOLACTONES
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, (2017/06/21)
Methods for forming 2-bromo, 2-fluoro ribofuranose intermediates and 2-chloro, 2- fluoro ribofuranose intermediates for use in preparing antiviral nucleosides are disclosed. Methods for forming nucleosides, and nucleoside prodrugs, using the intermediates, are also disclosed. The methods all produce intermediates, and the resulting nucleosides and prodrugs thereof, wherein the chirality of the carbon at the 2-position is controlled. In some embodiments, the chemistry involves using chiral auxiliaries, such as (R)-2,2-dimethyl-l,3- dioxolane-4-carbaldehyde, and in other embodiments, the chemistry involves using chiral starting materials, such as D-xylose.
Diastereoselective concise syntheses of the polyhydroxylated alkaloids DMDP and DAB
Bouillon, Marc E.,Pyne, Stephen G.
, p. 475 - 478 (2014/01/06)
A diastereoselective concise synthesis of the iminosugars DMDP and DAB is presented starting from l-xylose and affording the two alkaloids in good yields of 35% and 22% over seven and eight steps, respectively. The Petasis borono-Mannich reaction of 3,5-di-O-benzyl-l-xylofuranose with benzylamine and (E)-styrylboronic acid served as the nitrogen-introducing key step furnishing the new C-N bond in an entirely diastereoselective manner. A chemo- and regioselective O-mesylation followed by an intramolecular SN2- cyclisation allowed the formation of the pyrrolidine ring. Ozonolysis of the styryl double bond and subsequent reduction to form the C-5 hydroxymethyl substituent followed by hydrogenolysis of the benzyl protecting groups concluded the DMDP synthesis. Furthermore, an unexpected fragmentation process during the ozonolysis reaction also gave access to the C-5 decarbinolated DMDP derivative DAB.
Synthesis of purine nucleosides from D -glucuronic acid derivatives and evaluation of their cholinesterase-inhibitory activities
Xavier, Nuno M.,Schwarz, Stefan,Vaz, Pedro D.,Csuk, Rene,Rauter, Amelia P.
, p. 2770 - 2779 (2014/05/06)
Glucuronolactones were used as precursors for N9 and N 7 purine nucleosides containing glucuronic acid derivatives in their structures. Acetylated N-benzylglucofuran- and glucopyranuronamides were synthesized in a few steps from glucofuranurono-6,3-lactone. They were converted into the corresponding furanosyl and pyranosyl uronamide-based nucleosides by N-glycosylation with silylated 2-acetamido-6-chloropurine in the presence of trimethylsilyl triflate. The triacetylated bicyclic lactone was coupled itself with the nucleobase to give bicyclic N9,N7 nucleosides. Tri-O-acetylglucopyranurono-6,1-lactone was used for the first time as a glycosyl donor for N-glycosylation, and led to β-configured N9- and N7-linked purinylglucuronides under reaction conditions similar to those used with the 1-O-acetyl-substituted glycosyl donors. The cholinesterase inhibitory profiles of the synthetic nucleosides bearing glucuronic acid derivatives as glycons were evaluated, and they showed moderate selective acetylcholinesterase inhibitory activities (Ki = 14.78-50.53 μM). The best inhibition was shown by the furanosyl N 9-linked uronamide-based purine nucleoside. The synthesis of furanosyl and pyranosyl N9 and N7 purine nucleosides containing glucofuranurono-6,3-lactone, N-benzylglucuronamide, and glucuronic acid moieties is reported. Glucuronolactones were used as glycosyl donors or converted into suitable 1-O-acetyl derivatives for purine glycosylation. Some nucleosides showed moderate and selective inhibition of acetylcholinesterase. Copyright
Concise synthesis of (-)-steviamine and analogues and their glycosidase inhibitory activities
Jiangseubchatveera, Nadechanok,Bouillon, Marc E.,Liawruangrath, Boonsom,Liawruangrath, Saisunee,Nash, Robert J.,Pyne, Stephen G.
, p. 3826 - 3833 (2014/03/21)
A concise synthesis of (-)-steviamine is reported along with the synthesis of its analogues 10-nor-steviamine, 10-nor-ent-steviamine and 5-epi-ent-steviamine. These compounds were tested against twelve glycosidases (at 143 μg mL-1 concentrations) and were found to have in general poor inhibitory activity against most enzymes. The 10-nor analogues however, showed 50-54% inhibition of α-l-rhamnosidase from Penicillium decumbens while one of these, 10-nor-steviamine, showed 51% inhibition of N-acetyl-β-d-glucosaminidase (from Jack bean) at the same concentration (760 μM). This journal is The Royal Society of Chemistry 2013.
Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor. Part 2
Tanabe, Genzoh,Matsuoka, Kanjyun,Yoshinaga, Masahiro,Tsutsui, Nozomi,A. Amer, Mumen F.,Nakamura, Shinya,Nakanishi, Isao,Muraoka, Osamu,Xie, Weijia,Wu, Xiaoming,Yoshikawa, Masayuki
, p. 6321 - 6334,14 (2012/12/12)
To examine the role of the side chain of kotalanol (2), a potent natural α-glucosidase inhibitor isolated from Salacia reticulata, on inhibitory activity, four diastereomers (11a-11d) with reversed configuration (S) at the C-4′ position in the side chain were synthesized and evaluated. Two of the four (11b and 11d) significantly lost their inhibitory activity against both maltase and sucrase, while the other two (11a and 11c) sustained the inhibitory activity to a considerable extent, showing distinct activity in response to the change of stereochemistry of the hydroxyls at the 5′and 6′ positions. Different activities were rationalized with reference to in silico docking studies on these inhibitors with hNtMGAM. Against isomaltase, all four analogs showed potent inhibitory activity as well as 2, and 11b and 11d exhibited enzyme selectivity.
Synthesis of 3-fluoro-oxetane δ-amino acids
Lucas, Susana Dias,Rauter, Amelia Pilar,Schneider, Josef,Wessel, Hans Peter
experimental part, p. 431 - 446 (2011/06/19)
Starting from d-xylose, 2,4-anhydro-5-N-(tert-butoxycarbonyl)amino-5-deoxy- 3-fluoro-d-arabinonic acid 11 was synthesized over 10 steps including ring contraction, fluorination, and ester hydrolysis. Bromine oxidation of d-xylose followed by benzylidenati
O-acetyl-ADP-ribose non-hydrolyzable analogs
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Page/Page column 13, (2010/11/28)
Compounds, compositions and methods for modulating cell death in target cells, particularly cancer cells are provided. The compounds are analogs of O-acetyl-ADP-ribose (OAADPr).
Simple entry into isonucleosides: Synthesis of 6-amino-9-[(3S,4S,5R)-4- hydroxy-5-(hydroxymethyl)tetrahydrofuran-3-yl]purine
Mereyala, Hari Babu,Mamidyala, Sreeman Kumar
, p. 2965 - 2966 (2007/10/03)
A simple and efficient method for the preparation of isonucleoside 7 is described. The preparation of 1,4-anhydroxylitol 4, a key intermediate, is described by intramolecular cyclization of (2S,3R,4R)-3,5-dibenzyloxypentan-1,2, 4-triol 3 using diethyl car
Studies toward a synthesis of trilobatin B, a lignan from the liverwort Bazzania trilobata: Asymmetric construction of the tetrahydrofuran segment
Yoda, Hidemi,Nakaseko, Yuka,Takabe, Kunihiko
, p. 4217 - 4220 (2007/10/03)
A novel and stereocontrolled process is described for the asymmetric synthesis of the tetrahydrofuran segment of a 2,3-dicarboxy-6,7-dihydroxy-1- (3′,4′-dihydroxyphenyl)-1,2- dihydronaphthalene mono-ester, trilobatin B, a lignan from the liverwort Bazzani
Elucidation of the 2-C-methyl-D-erythritol 4-phosphate pathway for isoprenoid biosynthesis: Straightforward syntheses of enantiopure 1-deoxy-D-xylulose from pentose derivatives
Hoeffler, Jean-Fran?ois,Grosdemange-Billiard, Catherine,Rohmer, Michel
, p. 3065 - 3067 (2007/10/03)
Optically pure 1-deoxy-D-xylulose, a key metabolite for feeding experiments in the methylerythritol phosphate pathway for isoprenoid biosynthesis, is conveniently synthesised from 1,2-O-isopropylidene-α-D-xylofuranose or from D-arabinose. This renders lab
