4310-12-7

Upstream product

• 108-24-7 acetic anhydride 
• 474426-72-7 acetic 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic anhydride 
• 100-46-9 benzylamine 
• 62133-77-1 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronic acid 
• 489-91-8 D-glucuronic acid 

Relevant academic research and scientific papers

Synthesis of purine nucleosides from D -glucuronic acid derivatives and evaluation of their cholinesterase-inhibitory activities

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

Synthesis of some novel D-glucuronic acid acetylated derivatives as potential anti-tumor agents

A structurally diverse series of Δ4,5-uronamide derivatives have been chemically synthesized starting from D-glucuronic acid itself by means of acetylation, activation, amide bond formation and base-catalyzed elimination protocols. Structure el

Synthesis and enzymatic evaluation of substrates and inhibitors of β-glucuronidases

The phosphono and the tetrazolyl analogues 4 and 5 of 4-methylumbelliferyl β-D-glucuronide (= (4-methyl-2-oxo-2H-1-benzopyran-7-yl β-D-glucopyranosid)uronic acid; 6) were synthesized and evaluated as substrates of β-glucuronidases. Similarly, the phenylcarbamate 7 and its phosphono analogue 8 were prepared and evaluated as inhibitors. To examine the diastereoselectivity of the phosphorylation, we also synthesized the protected L-ido-, D-gluco-, and D-galacto-configurated phospha-glycopyranuronates 12, 13, 21, 22, 34 and 35. Two strategies were followed. In the first one, the glucuronic acid 19 was decarboxylated to 11 and further transformed, via 20, into the trichloroacetimidate 10. Phosphorylation of 10 with (MeO)3P yielded the diastereoisomers 12 and 13, the diastereoselectivity depending on the solvent. In MeCN, 12 and 13 were obtained in a ratio of 1:1, while in non-participating solvents the L-ido 12 was by far the major diastereoisomer. The acetate 11 was inert to (MeO)3P, but reacted with (PhO)3P to the anomeric mixture 21/22, in keeping with a stabilizing 1,3-interaction in the intermediate phosphonium salt. Similarly, the phospha-galacturonates 34 and 35 were prepared from the galactoside 23 via the enol ether 26, the lactone 27, and the acetates 28/29 that were also transformed into the trichloroacetimidate 33. In the second, higher-yielding strategy, phosphorylation of the pentodialdehyde 39 to 40/41 was followed by hydrolysis and acetylation to the phospha-glucuronates 43/44. Transesterification to 45/46, selective deacetylation to 48/49, and formation of the trichloroacetimidates 50/51 were followed by glycosidation and deprotection to 4. The tetrazole 5 was prepared from the lactones 54/55 via the N-benzylamides 57/58 that were treated with TfN3 to give the N-benzyltetrazoles 59/60. These were transformed into the trichloroacetimidates 63/64, glycosylated to 65, and deprotected. The O-carbamoylhydroximo-lactone 7 derived from the glucuronate 67/68, and the phosphonate analogue 8 were prepared by established methods. The phosphonate 4 is slowly hydrolyzed by the E. coli β-glucuronidase, but neither 4 nor the tetrazole 5 are affected by the bovine liver β-glucuronidase. The phenylcarbamate 7 of D-glucarhydroximo-1,5-lactone, but not its phosphonate analogue 8, is an inhibitor (K(I) = 8 μM) of the E. coli β-glucuronidase. The bovine liver β-glucuronidase is inhibited strongly by 7 (IC50 = 0.2 μM) and weakly by 8 (IC50 = 2 mM).