565450-93-3

Upstream product

• 98-88-4 benzoyl chloride 
• 385435-81-4 5-O-benzoyl-4-C-ethyl-1-O-methyl-b-D-ribofuranose 
• 55797-67-6 ((3aS,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4,4-diyl)dimethanol 
• 327614-72-2 5-O-(4,4'-dimethoxytrityl)-4-C-hydroxymethyl-2,3-O-isopropylidene-1-O-methyl-β-D-ribofuranose 
• 306960-27-0 5-O-(4,4'-dimethoxytrityl)-2,3-O-isopropylidene-1-O-methyl-4-C-vinyl-β-D-ribofuranose 
• 327614-88-0 5-O-(4,4'-dimethoxytrityl)-4-C-formyl-2,3-O-isopropylidene-1-O-methyl-β-D-ribofuranose 
• 33985-40-9 (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde 

Downstream Products

• 327614-73-3 1-O-acetyl-2,3,5-tri-O-benzoyl-4-C-ethyl-β-D-ribofuranose 

Relevant academic research and scientific papers

Synthesis and cytotoxicity of 4′-C- and 5′-C-substituted toyocamycins

Toyocamycin and some analogues have shown potent antitumor activities; however, none of them could be used clinically primarily owing to their cytotoxicity to normal human cells. In order to overcome the weakness of these nucleoside analogues, substitution of a variety of modified sugars for the ribofuranose was explored in our laboratories with expectation that certain sugar-modified toyocamycin analogues may be selectively cytotoxic to cancer cells. In this article, we report synthesis and cytotoxicity of 4′-C- and 5′-C-substituted toyocamycins, which were prepared via the condensations of 4-C- and 5-C-substituted ribofuranose derivatives 11, 12, 13, 20, 21, and 26 with the silylated form of 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine (27) and subsequent debromination and debenzoylation. When compared to the parent toyocamycin, all these analogues showed much lower cytotoxicity to human prostate cancer cells (HTB-81), mouse melanoma cancer cells (B16) as well as normal human fibroblasts. Compound 1e showed a significant cytotoxicity to the prostate cancer cells and a moderate selectivity. The results suggested that sugar modifications, especially those that may affect phosphorylation of nucleosides, could alter cytotoxicity profile significantly.