1001407-08-4

Basic information

• Product Name: N-[4-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyloxy)phenyl]-2-aminoacetamide
• Synonyms: N-[4-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyloxy)phenyl]-2-aminoacetamide
• CAS NO: 1001407-08-4
• Molecular Weight: 456.425
• Mol File: 1001407-08-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-[4-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyloxy)phenyl]-2-aminoacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[4-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyloxy)phenyl]-2-aminoacetamide(1001407-08-4)
• EPA Substance Registry System: N-[4-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyloxy)phenyl]-2-aminoacetamide(1001407-08-4)

Safety Data

• Hazardous Substances Data: 1001407-08-4(Hazardous Substances Data)

Upstream product

• 1001407-07-3 N-[4-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyloxy)phenyl]-2-(benzyloxycarbonylamino)acetamide 
• 1001407-04-0 4-aminophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranoside 
• 100-02-7 4-nitro-phenol 
• 1001407-03-9 4-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranoside 
• 34245-85-7 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranosyl bromide 

Downstream Products

• 1001407-06-2 N-{2-[4-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyloxy)phenyl]amino-2-oxoethyl}-4-{4-[bis(2-chloroethyl)amino]phenyl}butanamide 

Relevant articles and documents

Linker structure-activity relationships in fluorodeoxyglucose chlorambucil conjugates for tumor-targeted chemotherapy

Nitrogen mustards, such as chlorambucil (CLB), can cause adverse side-effects due to ubiquitous distribution in non-target organs. To minimize this toxicity, strategies of tumor-targeting drug delivery have been developed, where a cytotoxic warhead is linked to a tumor-cell-specific small ligand. Malignant cells exhibit marked glucose avidity and an accelerated metabolism by aerobic glycolysis, known as the Warburg effect, and recognized as a hallmark of cancer. A targeting approach exploiting the Warburg effect by conjugation of CLB to 2-fluoro-2-deoxyglucose (FDG) was previously reported and identified two peracetylated glucoconjugates 2 and 3 with promising antitumor activities in vivo. These results prompted us to investigate the importance of the spacer in this tumor-targeting glucose-based conjugates. Here we report the chemical synthesis and an in vitro cytotoxicity evaluation, using a 5-member panel of human tumor cell lines and human fibroblasts, of 16 new CLB glucoconjugates in which the alkylating drug is attached to the C-1 position of FDG via different linkages. We studied the structure-activity relationships in the linker, and evidenced the positive impact of an aromatic linker on in vitro cytotoxicity: compound 51 proved to be the most active FDG-CLB glucoside, characterized by a bis-aromatic spacer tethered to CLB through an amide function.

Conjugates of 2-fluoro-2-deoxy-glucose and their uses as anti cancer agents

The present invention relates to compounds of general formula (I): wherein: - R1, R2 and R3 mean, independently from the others, an hydrogen atom or an optionally substituted lower alkyl, a (C1-C7)acy