Evaluation of bis-triphenylphosphano-copper(I)-butyrate (C3H7COOCu(PPh3)2) as catalyst for the synthesis of 1-glycopyranosyl-4-substituted-1,2,3-triazoles

Bokor, Éva; Koppány, Csenge; Gonda, Zsombor; Novàk, Zoltán; Somsák, László

doi:10.1016/j.carres.2012.01.004

Cited by 12 publications

(8 citation statements)

References 32 publications

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“…The synthesis of 1-(β-D-glucopyranosyl)-4-hetaryl-1,2,3-triazoles was accomplished by the well-known copper(I)-catalyzed azide-alkyne cycloaddition [26,27] (CuAAc). Thus, the easily available 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl azide [28,29] (1) was treated with ethynyl heterocycles a and b in the presence of bis-triphenylphosphano-copper(I)-butyrate [30,31] to give the expected O-peracetylated 1-(β-D-glucopyranosyl)-4-(pyridin-2-yl)-and -4-(quinolin-2-yl)-1,2,3-triazoles (L-1a,b) in high yields (Table 1). Removal of the O-acetyl protecting groups of L-1a,b was effected by the Zemplén method, resulting in the unprotected derivatives L-3a,b in good yields.…”

Section: Chemistrymentioning

confidence: 99%

Ruthenium Half-Sandwich Type Complexes with Bidentate Monosaccharide Ligands Show Antineoplastic Activity in Ovarian Cancer Cell Models through Reactive Oxygen Species Production

Kacsir

Sipos

Ujlaki

et al. 2021

IJMS

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Ruthenium complexes are developed as substitutes for platinum complexes to be used in the chemotherapy of hematological and gynecological malignancies, such as ovarian cancer. We synthesized and screened 14 ruthenium half-sandwich complexes with bidentate monosaccharide ligands in ovarian cancer cell models. Four complexes were cytostatic, but not cytotoxic on A2780 and ID8 cells. The IC50 values were in the low micromolar range (the best being 0.87 µM) and were similar to or lower than those of the clinically available platinum complexes. The active complexes were cytostatic in cell models of glioblastoma, breast cancer, and pancreatic adenocarcinoma, while they were not cytostatic on non-transformed human skin fibroblasts. The bioactive ruthenium complexes showed cooperative binding to yet unidentified cellular target(s), and their activity was dependent on reactive oxygen species production. Large hydrophobic protective groups on the hydroxyl groups of the sugar moiety were needed for biological activity. The cytostatic activity of the ruthenium complexes was dependent on reactive species production. Rucaparib, a PARP inhibitor, potentiated the effects of ruthenium complexes.

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Section: Chemistrymentioning

confidence: 99%

Ruthenium Half-Sandwich Type Complexes with Bidentate Monosaccharide Ligands Show Antineoplastic Activity in Ovarian Cancer Cell Models through Reactive Oxygen Species Production

Kacsir

Sipos

Ujlaki

et al. 2021

IJMS

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“…Our work, summarized in Table 2 , started with O -perbenzylated C -glucosyl acetylene 1 described in the literature [ 45 ]. Copper catalyzed azide-alkyne cycloaddition (CuAAC) [ 46 ] was effected from 1 either by pre-formed aryl azides with CuO(CO)C 3 H 7 (PPh 3 ) 2 as the catalyst [ 47 ] (method a ) or azides obtained in situ from areneboronic acids [ 48 , 49 ] (method b ) to give 1,2,3-triazoles 2a–c in very good yields. Removal of the O -benzyl protecting groups from 2a by usual catalytic hydrogenation (method c ) gave excellent yield of 5a , however, under the same conditions 2c gave an inseparable product mixture.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of New C- and N-β-d-Glucopyranosyl Derivatives of Imidazole, 1,2,3-Triazole and Tetrazole, and Their Evaluation as Inhibitors of Glycogen Phosphorylase

et al. 2018

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The aim of the present study was to broaden the structure-activity relationships of C- and N-β-d-glucopyranosyl azole type inhibitors of glycogen phosphorylase. 1-Aryl-4-β-d-gluco-pyranosyl-1,2,3-triazoles were prepared by copper catalyzed azide-alkyne cycloadditions between O-perbenzylated or O-peracetylated β-d-glucopyranosyl ethynes and aryl azides. 1-β-d-Gluco-pyranosyl-4-phenyl imidazole was obtained in a glycosylation of 4(5)-phenylimidazole with O-peracetylated α-d-glucopyranosyl bromide. C-β-d-Glucopyranosyl-N-substituted-tetrazoles were synthesized by alkylation/arylation of O-perbenzoylated 5-β-d-glucopyranosyl-tetrazole or from a 2,6-anhydroheptose tosylhydrazone and arenediazonium salts. 5-Substituted tetrazoles were glycosylated by O-peracetylated α-d-glucopyranosyl bromide to give N-β-d-glucopyranosyl-C-substituted-tetrazoles. Standard deprotections gave test compounds which were assayed against rabbit muscle glycogen phosphorylase b. Most of the compounds proved inactive, the best inhibitor was 2-β-d-glucopyranosyl-5-phenyltetrazole (IC50 600 μM). These studies extended the structure-activity relationships of β-d-glucopyranosyl azole type inhibitors and revealed the extreme sensitivity of such type of inhibitors towards the structure of the azole moiety.

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“…1-(β- d -Glucosaminyl)-1,2,3-triazoles 25 were prepared first, and to this end, we turned back to an earlier work describing the synthesis of the fully protected derivatives 24 . The O -acetyl and N -phthaloyl protecting groups were removed simultaneously (Scheme ) by using 20 equiv of hydrazine hydrate in MeOH to give the required test compounds 25 in very good yields.…”

Section: Resultsmentioning

confidence: 99%

“…Pyridine (VWR) and Et 3 OBF 4 (Sigma-Aldrich) were purchased from the indicated suppliers. The 4-aryl-1-(2′-deoxy-2′-phthalimido-3′,4′,6′-tri- O -acetyl-β- d -glucopyranosyl)-1,2,3-triazoles ( 24a , b ), C -(2-deoxy-2-phthalimido-3,4,6-tri- O -acetyl-β- d -glucopyranosyl)formic acid ( 26 ), C -(2-deoxy-2-phthalimido-3,4,6-tri- O -acetyl-β- d -glucopyranosyl)formamide ( 30 ), and the 2-amino-1-arylethanone hydrochlorides were synthesized according to published procedures. Purity of the test compounds 25 , 29 , 33 , and 35 (≥95%) was determined by elemental analysis.…”

Section: Methodsmentioning

confidence: 99%

Nanomolar Inhibitors of Glycogen Phosphorylase Based on β-d-Glucosaminyl Heterocycles: A Combined Synthetic, Enzyme Kinetic, and Protein Crystallography Study

et al. 2017

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Aryl substituted 1-(β-d-glucosaminyl)-1,2,3-triazoles as well as C-β-d-glucosaminyl 1,2,4-triazoles and imidazoles were synthesized and tested as inhibitors against muscle and liver isoforms of glycogen phosphorylase (GP). While the N-β-d-glucosaminyl 1,2,3-triazoles showed weak or no inhibition, the C-β-d-glucosaminyl derivatives had potent activity, and the best inhibitor was the 2-(β-d-glucosaminyl)-4(5)-(2-naphthyl)-imidazole with a K value of 143 nM against human liver GPa. An X-ray crystallography study of the rabbit muscle GPb inhibitor complexes revealed structural features of the strong binding and offered an explanation for the differences in inhibitory potency between glucosyl and glucosaminyl derivatives and also for the differences between imidazole and 1,2,4-triazole analogues.

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Evaluation of bis-triphenylphosphano-copper(I)-butyrate (C3H7COOCu(PPh3)2) as catalyst for the synthesis of 1-glycopyranosyl-4-substituted-1,2,3-triazoles

Cited by 12 publications

References 32 publications

Ruthenium Half-Sandwich Type Complexes with Bidentate Monosaccharide Ligands Show Antineoplastic Activity in Ovarian Cancer Cell Models through Reactive Oxygen Species Production

Ruthenium Half-Sandwich Type Complexes with Bidentate Monosaccharide Ligands Show Antineoplastic Activity in Ovarian Cancer Cell Models through Reactive Oxygen Species Production

Synthesis of New C- and N-β-d-Glucopyranosyl Derivatives of Imidazole, 1,2,3-Triazole and Tetrazole, and Their Evaluation as Inhibitors of Glycogen Phosphorylase

Nanomolar Inhibitors of Glycogen Phosphorylase Based on β-d-Glucosaminyl Heterocycles: A Combined Synthetic, Enzyme Kinetic, and Protein Crystallography Study

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