327614-74-4

Basic information

• Product Name: C₃₆H₂₈BrN₅O₇
• Synonyms: C₃₆H₂₈BrN₅O₇
• CAS NO: 327614-74-4
• Molecular Weight: 722.552
• Mol File: 327614-74-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₃₆H₂₈BrN₅O₇(CAS DataBase Reference)
• NIST Chemistry Reference: C₃₆H₂₈BrN₅O₇(327614-74-4)
• EPA Substance Registry System: C₃₆H₂₈BrN₅O₇(327614-74-4)

Safety Data

• Hazardous Substances Data: 327614-74-4(Hazardous Substances Data)

Upstream product

• 327614-64-2 C₃₀H₂₈O₈ 
• 332363-24-3 Benzoic acid (R)-1-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-but-3-enyl ester 
• 332363-26-5 Benzoic acid (R)-1-((2S,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-but-3-enyl ester 
• 98-88-4 benzoyl chloride 
• 106220-93-3 (R)-1-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-but-3-en-1-ol 
• 19393-83-0 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine 
• 306960-58-7 1-O-acetyl-5(R)-C-allyl-2,3,5-tri-O-benzoyl-D-ribofuranose 

Downstream Products

• 332363-33-4 C₃₆H₂₉N₅O₇ 
• 332363-34-5 C₃₆H₃₁N₅O₇ 

Relevant articles and documents

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.