Synthesis of salacinol

Yuasa, Hideya; Takada, Jun; Hashimoto, H.

doi:10.1016/s0040-4039(00)01129-1

Cited by 80 publications

(50 citation statements)

References 8 publications

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“…[1][2][3] The molecular structure of this inhibitor is unique in that it contains a sulfonium ion (1, stabilized by an internal sulfate counterion (1′-deoxy-L-erythrosyl-3′-sulfate anion). [4][5][6] In this regard, we 5,7 and others 6 have previously reported the syntheses of salacinol (1) and its stereoisomers. [4][5][6] In this regard, we 5,7 and others 6 have previously reported the syntheses of salacinol (1) and its stereoisomers.…”

mentioning

confidence: 86%

Improved Syntheses of the Naturally Occurring Glycosidase Inhibitor Salacinol

Ghavami¹,

Sadalapure²,

Johnston³

et al. 2003

Synlett

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Improved syntheses of the naturally occurring sulfonium ion, salacinol are described. Salacinol is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of Type 2 Diabetes. The synthetic strategy relies on the nucleophilic attack of 2,3,5-tri-O-benzyl-or 2,3,5-tri-O-p-methoxybenzyl-1,4-anhydro-4-thio-Darabinitol at the least hindered carbon of benzylidene-protected L-erythritol-1,3-cyclic sulfate in 1,1,1,3,3,3-hexafluoro-2-propanol as solvent. The reactions are compared to those with the benzyl-protected L-erythritol-1,3-cyclic sulfate and also to those in acetone and 2-propanol. Excellent yields are obtained for the reactions with the benzylidene-protected cyclic sulfate. The synthetic route employing p-methoxybenzyl ether protecting groups is advantageous since all protecting groups in the adduct may be removed with trifluoroacetic acid to yield salacinol, thereby obviating the problematic deprotection of benzyl ethers by hydrogenolysis.

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confidence: 86%

Improved Syntheses of the Naturally Occurring Glycosidase Inhibitor Salacinol

Ghavami¹,

Sadalapure²,

Johnston³

et al. 2003

Synlett

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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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“…1) have been isolated from Salacia reticulata WIGHT, 3,4 and Salacia oblonga and Salacia chinensis, 5 traditionally used in the Ayurvedic system of India and Sri Lanka for the treatment of diabetes. 6 The sulfonium ion structure of these compounds has stimulated different groups to carry out the synthesis of salacinol, 7,8 and other carbohydrate-based cyclic sulfonium compounds, [9][10][11][12][13][14][15] such as 3 11 and 4 ( Fig. 2), 12 as a new class of glycosidase inhibitors.…”

Section: Introductionmentioning

confidence: 99%