66522-52-9

Usage

Uses

Used in Pharmaceutical Applications:
5'-sulfamoyl-2-chloroadenosine is used as an antiviral and antiparasitic agent due to its potential to target and inhibit the replication or function of viruses and parasites, thereby helping to treat or prevent infections.
Used in Cancer Therapy:
In the field of oncology, 5'-sulfamoyl-2-chloroadenosine is used as an angiogenesis inhibitor for its potential to prevent the formation of new blood vessels, which is a critical process in the growth and spread of cancerous tumors.
Used in Drug Development Research:
5'-sulfamoyl-2-chloroadenosine serves as a subject of research for drug development, as scientists investigate its mechanisms of action and explore its potential uses in medicine, including the treatment of various diseases and conditions.
Further research is necessary to fully understand the mechanisms of action and potential uses of 5'-sulfamoyl-2-chloroadenosine in medicine, ensuring its safety and efficacy for therapeutic applications.

Upstream product

• 532-20-7 D-Ribose 
• 103251-76-9 [(3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methyl sulfamate 
• 160473-70-1 5-O-sulfamoyl-1,2,3-tri-O-acetyl-β-D-ribofuranose 
• 103728-78-5 [(2R,3R,4R)-4,5-diacetoxy-2-(hydroxymethyl)tetrahydrofuran-3-yl] acetate 
• 55726-00-6 (3R,4S,5R)-5-((trityloxy)methyl)tetrahydrofuran-2,3,4-triol 
• 94482-37-8 5-O-triphenylmethyl-D-ribofuranose-1,2,3-triacetate 
• 160473-71-2 9-(2'-3'-di-O-acetyl-5'-O-sulfamoyl-β-D-ribofuranosyl)-2,6-dichloropurine 
• 67-56-1 methanol 

Relevant academic research and scientific papers

Hexafluoroisopropyl sulfamate: A useful reagent for the synthesis of sulfamates and sulfamides

Sulfamates and sulfamides are most often synthesized from alcohols and amines with sulfamoyl chloride, which is an unstable reagent. We have identified hexafluoroisopropyl sulfamate (HFIPS) as a bench-stable solid that reacts readily with a wide variety of alcohols, amines, phenols, and anilines under mild reaction conditions. The sole byproduct of the reaction is hexafluoroisopropanol (HFIP) and reaction products can often be isolated in high purity after an aqueous workup (optional) and removal of solvents by evaporation.

Synthesis, structure and bioactivity of primary sulfamate-containing natural products

Here we report the synthesis of natural products (NPs) 5′-O-sulfamoyl adenosine 1 and 5′-O-sulfamoyl-2-chloroadenosine 2. As primary sulfamates these compounds represent an uncommon class of NPs, furthermore there are few NPs known that contain a N–S bond. Compounds 1 and 2 were evaluated for inhibition of carbonic anhydrases (CA), a metalloenzyme family where the primary sulfamate is known to coordinate to the active site zinc and form key hydrogen bonds with adjacent CA active site residues. Both NPs were good to moderate CA inhibitors, with compound 2 a 20–50-fold stronger CA inhibitor (Ki values 65–234 nM) than compound 1. The protein X-ray crystal structures of 1 and 2 in complex with CA II show that it is not the halogen-hydrophobic interactions that give compound 2 a greater binding energy but a slight movement in orientation of the ribose ring that allows better hydrogen bonds to CA residues. Compounds 1 and 2 were further investigated for antimicrobial activity against a panel of microbes relevant to human health, including Gram-negative bacteria (4 strains), Gram-positive bacteria (1 strain) and yeast (2 strains). Antimicrobial activity and selectivity was observed. The minimum inhibitory concentration (MIC) of NP 1 was 10 μM against Gram-positive Staphylococcus aureus and NP 2 was 5 μM against Gram-negative Escherichia coli. This is the first time that NP primary sulfamates have been assessed for inhibition and binding to CAs, with systematic antimicrobial activity studies also reported.

A Novel Synthesis of Sulfamoyl Nucleosides

The sulfamoylated ribose derivative 8 was prepared on a kilogram scale, and used in conjunction with various heterocycles to prepare a series of natural and unnatural 5-O-sulfamoyl nucleosides (10 - 32).A modification of the Vorbrueggen-Hilbert-Johnson reaction conditions for nucleoside formation was used.