Recent advances in the chemistry of azapyranose sugars

Afarinkia, K.; Bahar, Akmal

doi:10.1016/j.tetasy.2005.02.020

Cited by 230 publications

(46 citation statements)

References 148 publications

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“…Dichloromethane, THF and MeOH were used as obtained from a Pure-Solv solvent purification system. (8). Compound 7 [20,24] (550 mg, 1.85 mmol) was dissolved in anhyd pyridine (4 mL) and DMAP (226 mg) was added.…”

Section: Methodsmentioning

confidence: 99%

“…This is presumably because they are not as readily available as pyranosides and their preparation is not trivial. [8,9] Potential advantages of investigating 1-deoxymannojirimycin (DMJ) [10] or 1-deoxynojirimycin (DNJ, 3, Figure 1) or other iminosugars compared with pyranosides as scaffolds include the possibility that the protonated ring nitrogen atom could contribute a charged hydrogen bonding group to enhance interactions of a particular ligand with a receptor. Also pharmacophoric groups can be grafted to the ring nitrogen.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Somatostatin Mimetics Based on 1‐Deoxynojirimycin

2008

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The synthesis of novel somatostatin mimetics from 1-deoxynojirimycin (DNJ) is described. The dipeptide mimetic, which respectively displayed the side chains of tryptophan and lysine at the nitrogen and O6 atoms of the iminosugar scaffold is a ligand (K(i)=3.2 microM) for the human somatostatin receptor subtype 4 (hSSTR4) but has lower affinity (K(i)>100 microM) for hSSTR5. A benzylated analogue of the Trp-Lys mimetic displays higher affinity for hSSTR5 (K(i)=5 microM).

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of Somatostatin Mimetics Based on 1‐Deoxynojirimycin

2008

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“…Iminosugars themselves have been of significant interest as glycosidase inhibitors [27] and some have found clinical use [28] prompting the development of a range of syntheses to these and related compounds. [29] The use of iminosugars as scaffolds for bioorganic and medicinal chemistry offers the possibility, not available to pyranosides, of incorporating a charged hydrogen-bond donor through protonation of the ring nitrogen atom which would occur at physiological pH. In addition pharmacophoric groups can be grafted to the nitrogen atom.…”

Section: Synthesis Of Non-peptide Peptidomimeticsmentioning

confidence: 99%

Peptidomimetics, Glycomimetics and Scaffolds from Carbohydrate Building Blocks

Murphy

2007

Eur J Org Chem

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Saccharides, due to their high density of functional groups and availability as chiral building blocks are scaffolds for bioactive compound discovery. Pyranosides and iminosugar‐based peptidomimetics have been synthesised as ligands for somatostatin receptors and HIV protease. The synthesis of polyhydroxylated macrolides related to natural products and cyclophanes has been achieved from carbohydrate fragments with a view to investigation of their potential as scaffolds. In addition, the trajectory of aromatic systems grafted to saccharides have been studied and this has led to the synthesis of probes for the study of carbohydrate protein interactions. These compounds include geometrically diverse bivalent glycomimetics derived from scaffolds that are hybrids of sugars and aromatic groups. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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“…Glycosidases are accordingly excellent therapeutic targets for a diverse range of diseases including lysosomal storage disorders, [6] cancer, [7] and special attention has been given to the treatment of HIV. [8] Among the various types of glucosidase inhibitors, iminosugars, [9] carbasugars [10] and thiosugars [11] have received the most attention because of their potent inhibitory activity and well established inhibition mechanisms, which are mainly competitive. Some carbocyclic glucosidase inhibitors include potent HIV inhibitors, such as conduritol epoxides and aminoconduritols, as well as conduritol A analogues, which modulate the release of insulin.…”

Section: Introductionmentioning

confidence: 99%

A Novel Competitive Class of α‐Glucosidase Inhibitors: (E)‐1‐Phenyl‐3‐(4‐Styrylphenyl)Urea Derivatives

et al. 2010

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Competitive glycosidase inhibitors are generally sugar mimics that are costly and tedious to obtain because they require challenging and elongated chemical synthesis, which must be stereo- and regiocontrolled. Here, we show that readily accessible achiral (E)-1-phenyl-3-(4-strylphenyl)ureas are potent competitive α-glucosidase inhibitors. A systematic synthesis study shows that the 1-phenyl moiety on the urea is critical for ensuring competitive inhibition, and substituents on both terminal phenyl groups contribute to inhibition potency. The most potent inhibitor, compound 12 (IC(50)=8.4 μM, K(i)=3.2 μM), manifested a simple slow-binding inhibition profile for α-glucosidase with the kinetic parameters k(3)=0.005256 μM(-1) min(-1), k(4)=0.003024 min(-1), and K(i)(app) =0.5753 μM.

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Recent advances in the chemistry of azapyranose sugars

Cited by 230 publications

References 148 publications

Synthesis of Somatostatin Mimetics Based on 1‐Deoxynojirimycin

Synthesis of Somatostatin Mimetics Based on 1‐Deoxynojirimycin

Peptidomimetics, Glycomimetics and Scaffolds from Carbohydrate Building Blocks

A Novel Competitive Class of α‐Glucosidase Inhibitors: (E)‐1‐Phenyl‐3‐(4‐Styrylphenyl)Urea Derivatives

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