1001407-07-3

Upstream product

• 34245-85-7 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranosyl bromide 
• 1001407-03-9 4-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranoside 
• 100-02-7 4-nitro-phenol 
• 1001407-04-0 4-aminophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranoside 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 

Downstream Products

• 1001407-08-4 N-[4-(3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-glucopyranosyloxy)phenyl]-2-aminoacetamide 
• 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 academic research and scientific papers

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

Synthesis and cytotoxic properties of new fluorodeoxyglucose-coupled chlorambucil derivatives

Frequently used in the treatment of malignant cells, alkylating agents, like most anticancer substances, produce adverse side effects caused by the toxicity of the agents toward normal tissues and lose efficiency through poor distribution to target sites.