74912-02-0Relevant articles and documents
An improved synthesis of a key intermediate for (+)-biotin from d-mannose
Chen, Fen-Er,Zhao, Jian-Feng,Xiong, Fang-Jun,Xie, Bin,Zhang, Ping
, p. 2461 - 2464 (2007)
An efficient and reproducible process for the synthesis of methyl 2,3,4,5-tetradeoxy-7,8-O-isopropylidene-d-arabino-nanonate (2), a key intermediate in the total synthesis of (+)-biotin (1), starting from readily available d-mannose is described. The cruc
Design, synthesis and pharmacological evaluation of omeprazole-like agents with anti-inflammatory activity
El-Nezhawy, Ahmed O.H.,Biuomy, Ayman R.,Hassan, Fatma S.,Ismaiel, Ayman K.,Omar, Hany A.
, p. 1661 - 1670 (2013/05/09)
A new series of novel benzimidazole derivatives containing substituted pyrid-2-yl moiety and polyhydroxy sugar conjugated to the N-benzimidazole moiety has been synthesized and evaluated as orally bioavailable anti-inflammatory agents with anti-ulcerogenic activity. The anti-inflammatory and anti-ulcerogenic activities of these compounds were compared to diclofenac and omeprazole, respectively. In carrageenan-induced paw oedema assay, 2-methyl-N-((3,4-dimethoxypyridin-2-yl)methyl)-1H-benzimidazol-5-amine (12d) and 1-(1,2,3,5-tetrahydroxy-α-d-mannofuranose)-5-(((3,4-dimethoxypyridin-2yl) methyl)amino)-2-methyl-1H-benzimidazole (15d) displayed dose-dependent anti-inflammatory activities by decreasing the inflammation by 62% and 72%, respectively which is comparable to that of diclofenac (73%). In contrast to diclofenac, the anti-inflammatory activity of these compounds was not only free from any side effects on the gastric mucosa but also showed significant anti-ulcerogenic activity in rat pyloric ligation and ethanol-induced gastric ulcer models similar to that of omeprazole. Together, these findings suggest that 12d and 15d are potent anti-inflammatory agents with concurrent anti-ulcerogenic activity and support its clinical promise as a component of therapeutic strategies for inflammation, for which the gastric side effects are always a major limitation.
Double reductive amination and selective strecker reaction of a D-lyxaric aldehyde: Synthesis of diversely functionalized 3,4,5-trihydroxypiperidines
Matassini, Camilla,Mirabella, Stefania,Goti, Andrea,Cardona, Francesca
, p. 3920 - 3924 (2012/09/08)
A D-mannose-derived aldehyde with the D-lyxo configuration is a versatile key intermediate to functionally and stereochemically diversified piperidines. It allowed the synthesis of natural 3,4,5-trihydroxypiperidines and new analogs through a double reductive amination strategy and the synthesis of novel 2-cyanotrihydroxypiperidines through a highly regio-and diastereoselective Strecker reaction.
1-C-Alkyl imino-d-xylitol and -l-arabinitol derivatives obtained via nucleophilic addition to pentose-derived N-tert-butanesulfinyl imines: Sugar- versus chiral auxiliary-induced stereoselectivity
Oulaidi, Farah,Gallienne, Estelle,Compain, Philippe,Martin, Olivier R.
, p. 609 - 612 (2011/06/28)
The stereoselective synthesis of 1-C-alkyl iminosugars in the d-xylo and l-arabino series as potential drugs for the treatment of lysosomal diseases has been achieved. The key step involves nucleophilic addition to pentodialdofuranose-derived imines gener
Chemoenzymatic synthesis of [3,9-13C]-labeled NeuAc and KDN
Sato, Ken-Ichi,Akai, Shoji,Hiroshima, Toshiyuki,Aoki, Hidenori,Sakuma, Mayumi,Suzuki, Ken-Ju
, p. 3513 - 3516 (2007/10/03)
The chemoenzymatic synthesis of 13C-labeled sialic acid (NeuAc) and 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) as useful molecular probes for studying the conformation of sialyl or KDN oligosaccharides attached to proteins was perform
A Synthetic Approach to the Squalestatins and Zaragozic Acids: Introduction of the C5 Stereocentre via an Ester-Enolate Claisen Rearrangement. The X-Ray Crystal Structure of an Intermediate
Gable, Robert W.,McVinish, Leasa M.,Rizzacasa, Mark A.
, p. 1537 - 1544 (2007/10/02)
In an overall plan to synthesize the anti-cholesterol agents the squalestatins and zaragozic acids, introduction of the C5 stereochemistry was achieved via an Ireland-Claisen rearrangement of the allyl ester (7) followed by methylation, which gives the es
Enantiospecific Synthesis of the Hexahydrofuran Unit of Erythroskyrine, a Pentaenoyltetramic Acid Metabolite
Jones, Raymond C. F.,Tankard, Mark
, p. 765 - 767 (2007/10/02)
A hexahydrofurofuran unit suitably functionalised for incorporation into the synthesis of erythroskyrine has been prepared in homochiral form from diacetone-D-glucose.
SYNTHESIS OF 5-AMINO-5-DEOXY-D-MANNOPYRANOSE AND 1,5-DIDEOXY-1,5-IMINO-D-MANNITOL, AND INHIBITION OF α- AND β-D-MANNOSIDASES
Legler, Guenter,Juelich, Elisabeth
, p. 61 - 72 (2007/10/02)
The title compounds and the corresponding L-gulo derivatives were synthesised in 6 steps from benzyl 2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside.The Ki values, determined from inhibition studies with α-D-mannosidases from jack beans, almonds, and calf liver, and β-D-mannosidase from Aspergillus wentii, ranged from 70 to 400 μM for the mannitol derivative and from 1.2 to 20 μM for 5-amino-5-deoxy-D-mannopyranose, i.e., inhibition is E2-E4-fold stronger than with D-mannose.Marked enhancement of inhibition with increasing pH is ascribed to the ionisation of a carboxyl group at the active site, forming an ion pair with the protonated inhibitor.The inhibition equilibrium between the jack-bean enzyme and the mannose derivative was approached slowly with kapp 2.0E5 M-1.min-1.The mannose-derived inhibitor was also inhibitory against β-D-glucosidases from almonds and Asp. wentii, with Ki values only 20-150-times larger than those for the inhibition of these enzymes by 5-amino-5-deoxy-D-glucopyranose.This moderate discrimination in binding of D-gluco and D-manno derivatives is in marked contrast to the high specificity shown by the glucosidase in catalysing the hydrolysis of mannosidases.A similar low specificity with respect to binding, combined with highly specific catalysis, was also seen with the mannosidases acting on inhibitors and substrates with the D-gluco configuration.
Synthese totale des acides (+) et (-) nonactique a partir de carbohydrates
Ireland, Robert E.,Vevert, Jean-Paul
, p. 572 - 583 (2007/10/02)
The synthesis of (-) and (+) nonactic acids (2a) and (2b) has been achieved starting from D-mannose (7) and D-gluono-γ-lactone (22) respectively.The key step in the synthesis is the -sigmatropic rearrangement of the silylated ketene-acetals IV leadin
