Oligosaccharide-camptothecin conjugates as potential antineoplastic drugs: Design, synthesis and biological evaluation

Design, Synthesis, and Evaluation of New Sugar-Substituted Imidazole Derivatives as Selective c-MYC Transcription Repressors Targeting the Promoter G-Quadruplex

“…The synthetic routes of key amine intermediates ( 35 – 37 , 40 , 41 , 43 , 48 – 51 ) and azide intermediates ( 30 , 31 , 53 ) are illustrated in Scheme A. To obtain the synthetic blocks of R groups with sugar, we first synthesized the synthetic blocks of the carbohydrate part (R′ group) according to a previously reported method, including intermediates 25 – 31 , which were derived from starting materials 18 – 20 in high yields. − On the other hand, the synthetic blocks of the linker were obtained from a commercial source ( 9 ) or by chemical synthesis ( 10 , 12 , and 57 ). , Then, treatment with activated glycosyl 25 – 27 and p -nitrophenol ( 9 ) or p -nitrophenol derivatives ( 10 , 12 ) was performed, yielding linker-coupled monosaccharide derivatives 32 – 34 , 38 , 39 , and 42 under the catalysis of BF 3 -OEt 2 , respectively, and these derivatives were conjugated in a β-configured manner, as confirmed by 1 H NMR analysis. Subsequently, the corresponding reductive amine compounds ( 35 – 37 , 40 , 41 , and 43 ) were derived from these nitro precursors with 5% Pd/C and H 2 .…”

Glyco-Coated CdSe/ZnS Quantum Dots as Nanoprobes for Carbonic Anhydrase IX Imaging in Cancer Cells

“…They were prepared by following a synthetic strategy that includes a key copper(I)-catalyzed azide-alkyne cycloaddition reaction (CuAAC) between the terminal alkyne residues of the DHLA-EDADA derivative 4 and the terminal azide residues of the sulfonamide derivative 5 ( Scheme 1 A) and the acetylated β-O-glucoside 6 , 29 respectively ( Scheme 1 B). The bifunctional di-alkyne derivative 4 was easily prepared in high yield (75% yield) by 2-(1 H -benzotriazole-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate (TBTU) mediated coupling of DHLA-EDADA 7 ( 25 ) with the commercially available propargylamine 8 ( Scheme 1 B).…”

“…Then, the tetracetate β-O-glucoside 6 ( Scheme 1 B), bearing a PEGylated linker at the anomeric position, was prepared by modifying a previously reported protocol ( Scheme S1 , Supporting Information). 29 Finally, the CuAACs were accomplished using a combination of copper(II) sulfate (CuSO 4 ) and sodium ascorbate in dry dimethylformamide (DMF) to afford ligands 2 and 13 in good yields (69% 2 and 62% 13 ; Scheme 1 B). The glucose residues of 13 were deacetylated under basic conditions (K 2 CO 3 , MeOH, 24 h, 57% yield) affording the divalent Glc-bearing ligand 3 .…”

“…Thereafter, the carboxylic group of the intermediate derivative 11 (Scheme A) was coupled with the commercially available 4-aminoethylbenzene sulfonamide 12 upon reaction with carbonyl diimidazole (CDI) to afford compound 5 in good yield (75% yield). Then, the tetracetate β-O-glucoside 6 (Scheme B), bearing a PEGylated linker at the anomeric position, was prepared by modifying a previously reported protocol (Scheme S1, Supporting Information) . Finally, the CuAACs were accomplished using a combination of copper­(II) sulfate (CuSO 4 ) and sodium ascorbate in dry dimethylformamide (DMF) to afford ligands 2 and 13 in good yields (69% 2 and 62% 13 ; Scheme B).…”

Catalytic Site-Selective Carbamoylation of Pyranosides

“…A preliminary modulation of the position and the substitution of the carbamate function suggested that analogs could display improved binding properties toward malignant cells . Several glycoconjugates featuring this carbamoylated monosaccharide were designed very recently that displayed selective cytotoxicity in vitro and encouraging antitumor activities in vivo . As a result, a novel anticancer chemotherapy approach could stem from the targeting properties of carbamoylmannose.…”