Metathesis access to monocyclic iminocyclitol-based therapeutic agents

• Ileana Dragutan,
• Valerian Dragutan,
• Carmen Mitan,
• Hermanus C.M. Vosloo,
• Lionel Delaude and
• Albert Demonceau

Beilstein J. Org. Chem. 2011, 7, 699–716, doi:10.3762/bjoc.7.81

• case of broussonetines is much more complicated. This subgroup is currently represented by 30 reported examples, all isolated from plant species and used in folk medicine in China and Japan. Most broussonetines display marked inhibitory activities on various glycosidase types, with selectivities

• , nojirimycin (NJ, trivial name for 5-amino-5-deoxy-D-glucopyranose) (59), the first alkaloid discovered that mimicks a sugar (originally isolated from Streptomyces filtrate but also found in other bacterial cultures and plant sources), is a potent glycosidase inhibitor. In aqueous solution nojirimycin exists

• (135), a naturally occurring iminocyclitol with a lipophilic substituent at the anomeric position, is active on α-glucosidase which is a valid proof that α-alkylation at C1 does not supress the glycosidase inhibitory effect. Its lack of activity on β-galactosidase once again indicates that the relative

Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors

• Georg Schitter,
• Elisabeth Scheucher,
• Andreas J. Steiner,
• Arnold E. Stütz,
• Martin Thonhofer,
• Chris A. Tarling,
• Stephen G. Withers,
• Jacqueline Wicki,
• Katrin Fantur,
• Eduard Paschke,
• Don J. Mahuran,
• Brigitte A. Rigat,
• Michael Tropak and
• Tanja M. Wrodnigg

Beilstein J. Org. Chem. 2010, 6, No. 21, doi:10.3762/bjoc.6.21

• related β-galactosidase mutants. Keywords: chemical chaperones; 1-deoxy-D-galactonojirimycin; iminosugars; lipophilic galactosidase inhibitor; N-modified iminosugars; Introduction Iminosugars such as compounds 1–4 (Figure 1) have been shown to be potent glycosidase inhibitors and useful tools for the

Synthesis of a new class of aminocyclitol analogues with the conduramine D-2 configuration

• Latif Kelebekli,
• Yunus Kara and
• Murat Celik

Beilstein J. Org. Chem. 2010, 6, No. 15, doi:10.3762/bjoc.6.15

• ][10][11], many of which are widely used for the treatment of diseases in humans, animals and plants [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15]. Glycosidase and related enzymes are involved in the biosynthesis of the oligosaccharide chains [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15

• of carbohydrate mimetics, which can be potent inhibitors of glycosidase (1–4) [11][12][13][14][15][16], we have developed a method for rapid entry to these compounds. Antibiotics containing an aminocyclitol unit have stimulated the development of synthetic methodologies [16] in the search for

• diols in the presence of p-toluenesulfonyl isocyanate for the introduction of the amino alcohol functionality. We are currently interested in the synthesis of cyclitols and their derivatives [25]. As a part of our program directed towards the synthesis of potential glycosidase inhibitors we used a

A divergent asymmetric approach to aza-spiropyran derivative and (1S,8aR)-1-hydroxyindolizidine

• Jian-Feng Zheng,
• Wen Chen,
• Su-Yu Huang,
• Jian-Liang Ye and
• Pei-Qiang Huang

Beilstein J. Org. Chem. 2007, 3, No. 41, doi:10.1186/1860-5397-3-41

• potent and selective glycosidase inhibitory activities. [13][14][15][16][17][18][19][20] (1R,8aS)-1-Hydroxyindolizidine 3 has been postulated as a biosynthetic precursor [21][22][23][24][25][26] of (+)-lentiginosine (1), (−)-2-epilentiginosine (2) and (−)-swainsonine, a potentially useful antimetastasis

Vinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis

• Roger Hunter,
• Sophie C. M. Rees-Jones and
• Hong Su

Beilstein J. Org. Chem. 2007, 3, No. 38, doi:10.1186/1860-5397-3-38

• (Figure 2). The latter is an indolizidine alkaloid that has received significant attention from the synthetic organic community in view of its potent biological activity as an α- and β-glycosidase inhibitor with promising anti-diabetic,[19] anti-cancer,[20] anti-viral [21] and anti-AIDS activity.[22] The

Indolizidines and quinolizidines: natural products and beyond

• Joseph P. Michael

Beilstein J. Org. Chem. 2007, 3, No. 27, doi:10.1186/1860-5397-3-27

• vertebrates; and both terrestrial and marine sources are represented. For example, two of the best-known and most widely investigated groups of 'simple izidine' alkaloids are the plant-derived polyhydroxylated indolizidines that function as potent glycosidase inhibitors, [2][3][4] and the alkylindolizidines

Synthesis and glycosidase inhibitory activity of new hexa- substituted C8-glycomimetics

• Olivia Andriuzzi,
• Christine Gravier-Pelletier,
• Gildas Bertho,
• Thierry Prangé and
• Yves Le Merrer

Beilstein J. Org. Chem. 2005, 1, No. 12, doi:10.1186/1860-5397-1-12

• glycosidase inhibitors obtained since this diversity is introduced in an ultimate step of the synthesis. Introduction There is a considerable interest in the design of molecules able to mimic carbohydrates which play critical roles in various biological events such as for example, cell-cell recognition and

Methods for the synthesis of polyhydroxylated piperidines by diastereoselective dihydroxylation: Exploitation in the two-directional synthesis of aza-C-linked disaccharide derivatives

• Andrew Kennedy,
• Adam Nelson and
• Alexis Perry

Beilstein J. Org. Chem. 2005, 1, No. 2, doi:10.1186/1860-5397-1-2

• which saturated polyhydroxylated nitrogen and oxygen heterocycles are linked by an all-carbon tether. The saturated oxygen heterocycle has the potential to mimic the departing sugar in a glycosidase-catalysed reaction and aza-C-linked disaccharide mimetics may, therefore, be more potent inhibitors of

• is protonated at physiological pH and the transition state for glycosidase-catalysed reaction is mimicked effectively.[6] Glycosidase inhibitors have potential in the treatment of viral infections,[7][8][9][10] cancer[11][12] and diabetes and other metabolic disorders.[13][14][15] Aza-C-linked